Converting aldehydes/ketones into amines is one of the most common C–N bond-forming approaches in pharmaceutical synthesis, monomer modification for materials, and fine chemical manufacturing. Reductive amination is popular largely because it can often be done “one-pot”: the carbonyl and amine first form an imine/iminium intermediate, which is then reduced to the target amine.
What truly challenges R&D and process teams is usually not “whether it works,” but whether the following three requirements can be met simultaneously:
1. Safety and compliance pressure: Classic cyanoborohydrides (e.g., NaBH₃CN) often deliver good selectivity in reductive amination, but once placed in an acidic environment—or if there is any risk of acid contact—they can bring a significant EHS and compliance burden associated with “cyanide-containing systems / potential release of highly toxic gas,” which is especially sensitive in scale-up scenarios.
2. Condition compatibility: Formation of imines/iminium species often benefits from protic media such as methanol/ethanol/water and/or a small amount of acid. However, many alternative reductants are either unstable/inefficient in such media, or they operate with a narrower side-reaction/selectivity window.
3. Scale-up reproducibility and controllability: Scale-up prioritizes stable charging, batch-to-batch consistency, gas evolution and exotherm management, and whether quench/workup can be controlled (in particular, “when significant gassing starts” and “how to end the reaction safely”).
Under these practical constraints, the literature and authoritative synthesis resources repeatedly highlight an approach: use BH₃–amine complexes to replace cyanide-containing reductants. Among them, 2-methylpyridine–borane (2-picoline borane, also called α-picoline–borane) is one of the most frequently cited options.
2. What is 2-methylpyridine–borane? A more manageable BH₃ source (amine–borane complex)
1. 2-Methylpyridine–borane (2-picoline·BH₃; also written as borane–2-methylpyridine complex / α-picoline–borane) is, in essence, a Lewis base–borane complex formed by BH₃ and 2-methylpyridine (a pyridine-type nitrogen Lewis base). Coordination of the pyridine nitrogen to BH₃ allows BH₃ to exist in a more stable, weighable, and relatively easier-to-handle complex form.
2. Its repeated mention in the literature and authoritative synthesis resources stems from a simple core idea: it “packages” the reducing power of BH₃ into a more manageable complex—making reductive amination more likely to achieve both “it works” and “it runs reliably.”
3. Note: Here, “more manageable/easier to handle” mainly means avoiding cyanide-containing systems and providing a more stable, weighable form—it does not mean “low risk.” 2-Methylpyridine–borane is still fundamentally a B–H-containing reductant. In regulatory/transport classifications it is often treated as water-reactive and capable of releasing flammable gas. For scale-up, moisture control, process venting/gas evolution, and a controlled quench must be designed and validated as hard safety boundaries.
2-Methylpyridine–borane in reductive amination: why it is often recommended, and what to watch for
Question | What is it / Why it matters | Which type of challenge from Part 1 does it address? | Notes (boundary conditions) |
What is it? | “A complex of BH₃ and 2-methylpyridine (a Lewis base–borane complex; pyridine–borane type): coordination ‘packages’ BH₃ into a more stable, weighable form.” | Scale-up cares more about “charging consistency / reproducibility” than simply “how strong the reducing power is.” | “More stable/more manageable” does not mean “risk-free”; it remains a B–H reductant—moisture control, gas evolution, and controllable quench must be treated as safety boundaries. |
Why is it used to replace NaBH₃CN? | Often cited as one option to replace cyanoborohydrides (e.g., NaBH₃CN), with the emphasis on reducing compliance pressure by avoiding cyanide-containing systems. | More favorable for “safety & compliance,” especially in systems that require acid to promote imine/iminium formation. | The key benefit is “removing cyanide-related concerns,” not “eliminating all EHS constraints”; scale-up still requires evaluation of gas evolution, heat release, and workup risks. |
What does “process-friendly” specifically mean? | Relatively easier storage and weighing help turn reductive amination into a “repeatable workflow.” | Addresses “scale-up reproducibility”: more consistent charging, easier batch alignment, and a more stable process window. | Without process control (temperature, addition mode, quench strategy), even a “process-friendly” reductant can still expose instability at scale. |
Why is it said to be more compatible with common one-pot conditions? (C=N formation and reduction can connect in the same system) | Reductive amination often proceeds in alcohols/mixed solvents with a small amount of acid or a protic environment to enable “imine formation → reduction.” It can more readily interface with these practical conditions. | Addresses “condition compatibility”: better chance to run both “imine formation needs” and the “reduction step” stably within one system. | Medium compatibility is still substrate-dependent: solubility, phase behavior, and matching the rates of imine formation vs reduction all determine the final usable window. |
What is the core takeaway? | Its value is often not “stronger,” but more likely to make reductive amination robust—offering a more engineered balance among compliance pressure, condition compatibility, and scale-up controllability. | Shifts focus from “can it be done” to “can it be reliably replicated and safely closed out.” | Whether scale-up succeeds still depends on incorporating key control points (process gassing/exotherm, quench and workup) into validation and records—not merely “switching to a different reductant.” |
3. Reaction mainline: the key tension is “build C=N first, then selectively reduce it”
Success in reductive amination usually does not hinge on “directly reducing the carbonyl,” but on whether two things can be achieved simultaneously:
① Can C=N (imine/iminium) be established smoothly under suitable conditions?
② Does reduction occur preferentially at C=N (especially the iminium) rather than at competing substrates such as C=O?
This is why “reagent and condition selection” often determines success or failure more than the reaction equation itself.
Mainline step | What happens | Most sensitive control variables | Common failure modes (why it becomes unstable) | What “works well” looks like |
① Establishment of C=N (equilibrium step) | The carbonyl and amine first form a C=N intermediate: primary amines more often proceed via imines, while secondary amines more often proceed via the iminium pathway; this process is a reversible equilibrium. Carbonyl + amine ⇄ C=N intermediate | Solvent and water content / degree of dehydration; acidity (“mildly acidic window”); substrate solubility and phase behavior. | Too much water or insufficient dehydration shifts equilibrium back to the carbonyl; acidity too weak makes C=N formation slow; acidity too strong over-protonates the amine, reducing nucleophilicity and slowing formation instead. | It can operate within a medium/acidity window that favors C=N formation (rather than failing or losing selectivity as soon as alcohols/water/a small amount of acid are present). |
② Selective reduction (key step) | A hydride reduces C=N (especially the iminium) to the amine, thereby “locking in” the C–N bond. | Reductant selectivity and reactivity; addition mode and temperature; acidity and ionic environment. | The reductant preferentially reduces C=O (forming alcohol) or triggers broad side reductions; reduction that is too fast/too slow causes mismatch with the C=N formation rate. | It focuses reduction on C=N while suppressing competing pathways (e.g., direct carbonyl reduction, or nonselective reduction of other functional groups). |
③ The coupling key: matching the C=N formation rate with the reduction rate | Imine formation and reduction are not independent steps—they are coupled in rate and equilibrium. If C=N formation is slow or unstable, even a strong reductant can drive the system toward side reactions. | The combined set of “acidity × water content × solubility/phase behavior × addition rhythm.” | Works in small scale but unstable in scale-up: often due to heat/mass transfer changes that cause rate mismatch, and uncontrolled gassing/exotherm and quench. | “Works well” is not “stronger,” but “easier to stabilize this coupled relationship”: a broader window, fewer conflicts, and stronger controllability. |
4. Making Reductive Amination Robust: A Reproducible Window, Minimal Validation, and a Troubleshooting Path
4.1 Four “knobs” determine robustness (operationalizing the coupled relationship)
The reason reductive amination can work in small scale yet drift during scale-up is often not a single variable, but the combined effect of four knobs that together determine how well “C=N formation rate/equilibrium” matches “reduction rate/selectivity”:
1. Acidity window: It must promote C=N formation, but must not fully “deactivate” the amine.
2. Water content / degree of dehydration: The more water present, the harder it is for the C=N equilibrium to move forward; however, completely anhydrous conditions are not always optimal (depending on the system and substrate).
3. Solvent and phase behavior (solubility / mass transfer): Whether the flask is truly one phase or two phases—and whether the amine and carbonyl actually contact effectively—often determines rate and selectivity more directly than the “solvent category” itself.
4. Charging and process rhythm (temperature control / addition / close-out): This determines whether the reduction step acts mainly on the C=N intermediate (instead of switching to competing substrates), and directly affects whether gas evolution/exotherm and the quench–close-out process are controllable and reproducible.
4.2 Three rapid checks: confirm the reaction is on the right track
What you need to confirm | How to judge | If not satisfied, it typically means… |
The system is actually forming C=N (imine/iminium) | Early in the reaction you can observe C=N-related signals / an intermediate trend (or at minimum: the rate logic of carbonyl consumption and target amine formation is consistent) | C=N formation is too slow / equilibrium is pulling back: mismatch in acidity, water content, phase behavior, or substrate reactivity |
Reduction mainly occurs at C=N, rather than reducing C=O first | In the byproducts, the “alcohol (direct C=O reduction)” does not rise significantly | The reductant/conditions are too biased toward C=O, or C=N formation cannot keep up, so the competing pathway dominates |
The reaction can be “ended in a controlled way” | At close-out the reaction stops smoothly: quench proceeds steadily, gas evolution is not violent, and workup does not show sudden exotherm/violent foaming or other runaway behavior | Many scale-up issues occur at “close-out” rather than mid-reaction: you must design and lock in the quench and addition rhythm in advance (write it into the procedure), rather than focusing only on maximizing yield |
4.3 Troubleshooting decision table: observation → likely root cause → next adjustment
What you observe | Likely root cause to check first | Priority adjustment (what to do next) |
High residual carbonyl, slow increase of target amine | Slow C=N formation / equilibrium pulling back | First check water content/dehydration and the acidity window; then check phase behavior (two-phase? insufficient solubility?) |
Low target amine, but alcohol byproduct is obvious | Reduction is occurring preferentially at C=O (aldehyde/ketone is reduced to alcohol first) | Reduce the “C=O-sensitive” condition conflict: make C=N build faster (acidity/phase behavior), and match reduction rate to formation rate |
Small-scale looks good, but scale-up becomes highly variable (batch instability) | Heat/mass transfer changes cause rate mismatch; inconsistency in addition and temperature control | Fix critical process parameters: temperature control, addition rhythm, stirring/phase-behavior consistency; manage close-out/quench as a scale-up critical point |
Tail-end drags; total time becomes long | Late-stage slowdown: C=N formation/reduction rate drops; or as product/salts accumulate the system shifts from one phase to two phases, viscosity rises / mass transfer worsens, reducing effective contact | First check whether “the system has changed”: salt/byproduct build-up, phase split/emulsification/viscosity changes; also check whether acidity shifts during the run (more acidic or less), and whether inhibitory salts/ionic environments form |
4.4 The check order for making reductive amination “robust”
1. Check phase behavior and solubility first: Is it one phase or two phases? Do the amine and carbonyl truly contact sufficiently; is the mixture homogeneous after stirring?
2. Then set the acidity window: Is acidity sufficient to promote C=N formation while not overly suppressing the amine’s nucleophilicity?
3. Then control water content / degree of dehydration: Is water pulling the C=N equilibrium back toward the carbonyl side, preventing intermediate accumulation?
4. Then tune process rhythm (temperature / addition): Is the reduction step mainly targeting C=N; are the formation and reduction rates matched?
5. Finally, write close-out/quench into the procedure and validate it: Scale-up is not only about yield, but whether the reaction and workup can be ended smoothly, safely, and reproducibly.
5. Product Navigation Table｜2-Methylpyridine–Borane (2-Picoline·BH₃) Reductive Amination: Quickly Choose Which Table to Use by Experimental Task (Tables 1–3)
Research / experimental need | Which table to look at first | Why start with that table | Representative products in that table |
Get reductive amination “working” first: choose a suitable reductant system (both mainline and controls) | Table 1 Core reductants and borane/borohydride systems | Success/failure is often determined first by the reductant’s selectivity window: does it favor imine/iminium reduction, or does it more readily reduce the carbonyl directly? This also determines operability and the control/benchmark plan | 2-Methylpyridine–borane complex (2-Picoline·BH₃), STAB, sodium cyanoborohydride, sodium borohydride, borane–pyridine / THF·BH₃ / Me₂S·BH₃ |
Build a benchmark/control set: compare 2-Picoline·BH₃ with mainstream reductants side-by-side (rate/selectivity/substrate fit) | Table 1 | Changing only the reductant on the same substrate is the fastest “strategy control”: it quickly tells you whether the issue is the “reductant window” or the upstream “imine formation/acidity/water control” | 2-Picoline·BH₃ vs STAB vs sodium cyanoborohydride vs sodium borohydride; BH₃-complex controls |
Low conversion / slow reaction: suspect “slow imine formation / too much water / wrong acidity” | Table 2 General reaction environment & workup components (check Table 1 in parallel if needed) | Most of these issues are not about “whether the reductant is strong enough,” but whether imine/iminium formation is being driven: acid source, buffering, water management, and Lewis-acid synergy are often more decisive | TFA, p-toluenesulfonic acid monohydrate, formic acid, ammonium acetate, 4Å molecular sieves, titanium tetraisopropoxide, anhydrous methanol |
Many side reactions (e.g., direct carbonyl reduction / extra peaks): need to pull selectivity back to the imine/iminium pathway | Table 1 + Table 2 (Table 1 first, then fine-tune with Table 2) | First select the right reductant window (more biased toward imine/iminium reduction) via Table 1, then tune acidity/water control via Table 2 to “form only, reduce only along the target pathway” | Table 1: 2-Picoline·BH₃, STAB, sodium cyanoborohydride; Table 2: TFA/p-toluenesulfonic acid, ammonium acetate, 4Å molecular sieves |
Make conditions reproducible and scalable: standardize solvent water content, drying/water control, and workup | Table 2 | Scale-up and reproducibility most often drift due to “water, acid/base, and workup” variation; Table 2 focuses on engineering elements such as solvent dryness, water control, quench/neutralization, and drying | Anhydrous methanol, 4Å molecular sieves, water, sodium bicarbonate, sodium acetate, magnesium sulfate / sodium sulfate |
Workup is stuck: emulsions / poor phase split, residual acid, product salt hard to liberate | Table 2 | These problems are typically solved by a structured “quench–neutralize–dry–re-extract” workflow; the key is choosing the right combination of water/base/salt/drying agent | Water, sodium bicarbonate, sodium acetate, magnesium sulfate, sodium sulfate |
Need an alternative route or mechanistic confirmation: consider whether “imine formation + catalytic hydrogenation” is more suitable | Table 3 Control routes & methodology validation | Table 3 provides tools for switching to a “metal-catalyzed hydrogenation” control route to diagnose whether the bottleneck is intrinsic to borane/borohydride systems | Palladium powder, platinum oxide |
Pharma/high-requirement projects: focus on metal impurities and QC (or compare impurity risks of “metal hydrogenation vs borane systems”) | Table 3 (check Table 2 in parallel if needed) | Table 3 provides catalysts for a “metal-hydrogenation control route” and the logic for monitoring metal residues; for quantitation, select elemental standards matching the actual catalyst metal used (Pd/Pt/Ru/Ni…), with Ni standard listed here as an example | Nickel standard solution for water quality (Ni standard) |
Substrate fit / site-selectivity validation: use “model amines / drug-like amines” to probe the operating window first | Table 3 (check Table 1 in parallel if needed) | Table 3 consolidates more realistic, complex amine substrates/models to validate site selectivity and reproducibility; then return to Table 1 to choose the reductant system | Procainamide hydrochloride, 4-amino-N-(2-diethylaminoethyl)benzamide, 2-aminobenzamide |
Table 1｜Core Reductants and Borane/Borohydride Systems (Including Controls/Alternatives)
Category | CAS No. | Aladdin Cat. No. | Product name | Spec / purity | Key features & applications |
Mainline reductant｜2-Picoline·BH₃ (core) | 3999-38-0 | 2-Methylpyridine–borane complex | ≥95% | Mainline reductant: selectively reduces imines/iminium species in reductive amination, typically balancing practical stability with functional-group tolerance. Well-suited to making “imine formation → reduction” a more controllable two-step coupled process (the operating window should be optimized based on substrate and acidity). | |
Reductant / classic mainstream｜STAB system | 56553-60-7 | Sodium triacetoxyborohydride (STAB) | ≥90% | One of the most widely used reductants for reductive amination: more tolerant of mildly acidic conditions and commonly used for in situ reduction of imine/iminium formed from amines and carbonyls. Can serve as a mainstream benchmark vs 2-Picoline·BH₃ to compare side reactions (e.g., direct carbonyl reduction) and substrate compatibility. | |
Reductant / classic benchmark｜Cyanoborohydride (Borch system) | 25895-60-7 | Sodium cyanoborohydride | ≥95% | Classic benchmark reductant for reductive amination: under mildly acidic conditions it tends to favor reduction of imines/iminium while less readily reducing carbonyls directly. Often used to compare selectivity, rate, and substrate scope vs 2-Picoline·BH₃ (note its system characteristics and compliance management requirements). | |
Reductant / control｜Borane-type reductant (alternative system) | 74-94-2 | Dimethylamine borane | Suitable for synthesis | A representative “mild hydrogen source/hydride donor,” usable as a control reductant system versus 2-Picoline·BH₃ in reductive amination (to compare reaction rate, functional-group tolerance, and byproduct profile). | |
Reductant / control｜Strong borohydride | 16940-66-2 | S432207 | Sodium borohydride (explosive precursor) | purum p.a., ≥96% (gas-volumetric) | As a stronger hydride reductant, it can be used for reactivity/selectivity benchmarking vs 2-Picoline·BH₃: NaBH₄ more readily reduces carbonyls directly rather than “forming an imine first, then reducing,” making it useful for assessing side-reaction risk and substrate tolerance differences (with appropriate compliance and safety management). |
Reductant / upstream borane source｜BH₃ complex (control/alternative) | 110-51-0 | Borane–pyridine complex | ≥95% | One ligand-stabilized form of BH₃: can serve as a structural and reactivity control vs 2-Picoline·BH₃ (both are “pyridine–borane” types), useful for evaluating how ligand differences affect stability/solubility/selectivity. | |
Reductant / upstream borane source｜BH₃ complex (control/alternative) | 14044-65-6 | B110263 | Borane–tetrahydrofuran complex | 1.0 M in THF, with 5 mmol sodium borohydride stabilizer | A common solution-form BH₃ reductant; can be used as a control system for reductive amination or related reductions, and to understand the stability/operability advantages of 2-Picoline·BH₃ vs solution BH₃ (this system is more dependent on strictly anhydrous conditions). |
Reductant / upstream borane source｜BH₃ complex (control/alternative) | 13292-87-0 | Borane–dimethyl sulfide complex | 9.8 M in Dimethylthioamidine | A highly active BH₃ donor often used for more forcing reductions; in reductive amination it can be treated as an upstream borane source / “strong-reduction” control vs 2-Picoline·BH₃ to compare “higher reactivity but higher sensitivity” system differences. |
Table 2｜General Components for Reaction Environment and Workup (Acids/Bases/Salts/Solvents/Water Control/Drying)
Category | CAS No. | Aladdin Cat. No. | Product name | Spec / purity | Key features & applications |
Reaction environment control｜Strong acid (salt formation / iminium generation) | 76-05-1 | Trifluoroacetic acid (TFA) | Anhydrous grade, ≥99% | Commonly used to convert amine substrates into controlled salts / promote iminium formation, widening the selectivity window in reductive amination; because it is relatively strong, it is typically used catalytically / for salt formation rather than in large excess (to avoid unnecessary consumption of borane reagents). | |
Reaction environment control｜Acid catalysis (non-volatile strong acid) | 6192-52-5 | p-Toluenesulfonic acid monohydrate | Chemical pure (CP), ≥98% | Frequently used to promote imine/iminium formation (acid catalysis/salt formation), especially when a stronger, non-volatile acid is needed. With 2-Picoline·BH₃ it helps focus reduction on the iminium pathway (balance acid loading vs reductant consumption). | |
Reaction environment control｜Acid source / acid catalysis (also usable for quench) | 64-18-6 | F433212 | Formic acid (FA) | Pharma grade, PharmPure™, ≥98% | A mild acid source to promote “amine + carbonyl → imine/iminium,” helping 2-Picoline·BH₃ favor imine/iminium reduction; also often used for controlled quenching of active hydride after reaction (system-dependent). |
Reaction environment control｜Buffer / ammonium salt (also an ammonia-source alternative) | 631-61-8 | Ammonium acetate | HPLC grade, ≥99% | Common mild buffer/ammonium-salt system in reductive amination; in converting carbonyls to primary amines, it is also often used as an ammonia-source alternative (depending on the system). With 2-Picoline·BH₃ it can help keep acidity in a milder range. | |
Workup / buffering & salting-out｜Acetate system | 127-09-3 | Sodium acetate, anhydrous | For electrophoresis, ≥99% | A weakly basic buffer / pH-adjusting component: after acid-catalyzed reductive amination (TFA/p-TsOH, etc.), it can be used to gently bring pH back up and reduce side-reaction risks associated with excessive acidity (primarily for process/workup use). | |
Workup / neutralization｜Bicarbonate wash | 144-55-8 | Sodium bicarbonate | Pharma grade, PharmPure™ | A typical base-wash/neutralization reagent after acidic steps: used to liberate amine products from their salt forms to free bases, or to neutralize residual acids such as TFA/p-TsOH, facilitating extraction and purification. | |
Reaction solvent｜Alcohol solvent (also for cleaning/workup) | 67-56-1 | Methanol | Anhydrous grade, ≥99.8%, H₂O ≤100 ppm | A common solvent or co-solvent in 2-Picoline·BH₃ and many reductive amination systems; anhydrous methanol helps reduce water’s drag on imine formation (final choice still depends on substrate and reductant compatibility). | |
Workup / aqueous operations｜Water for quench/extraction | 7732-18-5 | Water | For biotechnology, nuclease-free, sterile | Used after reductive amination to quench residual borane/borohydride and proceed to aqueous workup (washing, phase separation); also used to prepare subsequent neutralization/buffer solutions. | |
Reaction water control｜Dehydrating aid | 70955-01-0 | M406640 | Molecular sieves, 4 Å | beads, 1–4 mesh | A commonly used water-control additive in reductive amination: removes water to push equilibrium toward imine/iminium, helping 2-Picoline·BH₃ reduction focus on the target pathway and improving conversion and reproducibility. |
Reaction additive / Lewis acid｜Carbonyl activation / dehydration synergy | 546-68-9 | Titanium tetraisopropoxide | Packaged for deposition systems | Ti(OR)₄ reagents can act as Lewis-acid / dehydration-synergy additives: activate carbonyls and promote imine formation, enhancing subsequent 2-Picoline·BH₃ reduction efficiency toward imine/iminium (especially valuable for substrates that form imines poorly). | |
Workup / drying｜Inorganic drying agent | 7487-88-9 | Magnesium sulfate | Anhydrous grade, high purity, reagent grade, ≥99.5% | A “faster” organic-phase drying agent (typically faster than Na₂SO₄), useful for quick small-scale extract drying after reductive amination to reduce impacts of residual water on product stability/purification. | |
Workup / drying｜Inorganic drying agent | 7757-82-6 | Sodium sulfate | Anhydrous grade, AR, granulated for organic trace analysis | Standard drying agent after organic extraction, improving workup reproducibility (reducing phase split/emulsification and downstream decomposition driven by residual water). |
Table 3｜Control Routes and Methodology Validation (Catalysts/Standards/Model Substrates/Precursor Controls)
Category | CAS No. | Aladdin Cat. No. | Product name | Spec / purity | Key features & applications |
Catalytic hydrogenation / control｜Noble-metal catalyst | 7440-05-3 | Palladium, 99+ powder | Suitable for analysis, top grade, ≥99% | Used to switch the reductive amination route to an “imine formation + catalytic hydrogenation” control (under H₂). Enables comparison of the “no external gas-source reduction” advantage of 2-Picoline·BH₃ and differences in substrate sensitivity. | |
Catalytic hydrogenation / control｜Noble-metal catalyst | 1314-15-4 | Platinum oxide | Pt, 80–86% | A typical hydrogenation catalyst component; can serve as a control route vs 2-Picoline·BH₃ (form imine/iminium then hydrogenate), for comparing how different reduction modes affect functional groups, impurity profiles, and scale-up feasibility. | |
Analysis / QC｜Residual monitoring for metal-catalysis routes (example: Ni standard) | 7440-02-0 | Nickel standard solution for water quality | Concentration: 1.39 mg/L; matrix: water | For residue monitoring/method validation when using metal-catalyzed control routes or introducing metal additives: supports ICP/AA quant workflows, spike recovery, and cross-contamination checks. In practice, select elemental standards matching the catalyst metal used (Pd/Pt/Ru/Ni, etc.); Ni is listed here as an example. | |
Mainline-related｜2-Picoline·BH₃ ligand/precursor and base control | 109-06-8 | 2-Methylpyridine (2-picoline) | Standard for GC, ≥99.5% (GC) | The ligand/source molecule and a methodological control for 2-methylpyridine–borane (2-Picoline·BH₃); also a reference basic nitrogen component when studying acid–base balance (primarily for “system understanding/control” purposes). | |
Amine substrate / model compound｜Derivatization control for drug-like amines | 614-39-1 | Procainamide hydrochloride | Moligand™, ≥98% | A drug-like amine/model substrate: used to evaluate 2-Picoline·BH₃ selectivity, salt-form control, and workup convenience in reductive amination (N-alkylation derivatization) on complex amine substrates. | |
Amine substrate / model compound｜Derivatization control for drug-like amines | 51-06-9 | 4-Amino-N-(2-diethylaminoethyl)benzamide | Moligand™, ≥97% | A model substrate with multiple amine sites and an amide scaffold, useful for testing site selectivity and the “acidity window–side reaction” relationship in 2-Picoline·BH₃ reductive amination (primarily for method validation/control). | |
Amine substrate / model substrate｜Aromatic amine (for reductive amination derivatization) | 88-68-6 | 2-Aminobenzamide | ≥98% | A representative aromatic amine substrate: useful for testing imine formation efficiency, aromatic amine reactivity, and functional-group tolerance in 2-Picoline·BH₃ reductive amination; more direct as a method-development/condition-screening control. |
Note: The above list contains representative Aladdin products. For additional specifications, please refer to the product list at the end of the article, or search the Aladdin website using “product name / CAS / catalog number.”
Aladdin: https://www.aladdinsci.com/