4-butyl-2-methylaniline - Reagent grade

Cat. No.: B483595

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

No vendor-validated bioassay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent. For synthetic applications, follow standard organic chemistry procedures relevant to anilines (see Reaction Conditions and Synthetic Utility). If you require a procedure tailored to this substrate (e.g., selective bromination or Boc-protection), contact technical support with your reaction context for protocol suggestions.

Biological Roles

This product is an anthropogenic aromatic amine used as a chemical building block; it does not have a known endogenous biological role.

• General biochemistry of anilines (literature context)
  • Primary arylamines can undergo N-acetylation (by arylamine N-acetyltransferases) and N-oxidation in biological systems; metabolites may include N-acetyl derivatives or hydroxylamines.
  • Protonation state: in physiological media, anilines are partially protonated (pKaH ~4–6), affecting membrane permeability and distribution.
• Research relevance
  • Hydrophobic aniline motifs are common in medicinal chemistry scaffolds; this specific substitution pattern provides steric/electronic tuning but is used strictly as a synthetic intermediate in research.

No clinical or therapeutic claims are made or implied. For laboratory research use only, as stated in the Product Data.

Buffer Applications

Not typically applicable. 4-butyl-2-methylaniline is not a buffering reagent or a component of standard biochemical buffer systems. If pH control is required during reactions (e.g., diazotization or coupling), use appropriate mineral acids/buffers; the amine can be handled as its protonated salt to improve aqueous compatibility.

Green Alternatives

While the compound itself is a specific building block (no direct substitute for identical structure), greener choices can be made in how it is used, purified, and transformed.

• Solvent selection (preferable options, literature/guidelines)
  • Replace chlorinated solvents (DCM, DCE) with toluene, ethyl acetate, 2-MeTHF, cyclopentyl methyl ether (CPME), or dimethyl carbonate where feasible.
  • For diazotization/azo coupling, use aqueous/EtOH or aqueous/AcOH systems when compatible.
• Coupling chemistry
  • Consider ligand-efficient Pd catalysis in greener solvents (2-MeTHF, CPME) or Cu-catalyzed Chan–Lam couplings in alcohols under air (minimizes strong bases and high temperatures).
• Protection/minimization strategies
  • Avoid unnecessary protection–deprotection by choosing chemoselective acylation/coupling conditions.
• Workup and purification
  • Favor crystallization/trituration over silica chromatography; switch to higher b.p. greener eluents (heptane/EtOAc) instead of hexanes/DCM.
• Energy efficiency
  • Employ microwave or flow reactors to reduce reaction times and energy consumption; use catalytic over stoichiometric reagents when possible.

Comparison snapshot (general)

• DCM vs toluene/EtOAc: lower toxicity and VOC impact with toluene/EtOAc; DCM may be required for low-temperature acylations—evaluate substitution.
• DMF/NMP vs 2-MeTHF/CPME: polar aprotics offer high solvency but carry reproductive toxicity flags; ether alternatives may work for many amide couplings/cross-couplings with optimized bases/ligands.

All suggestions are general process-intensification/green-chemistry principles; confirm compatibility with your specific transformation.

Pharmaceutical Uses

• Formulation/excipient status
  • Not a recognized pharmaceutical excipient. No pharmacopeial monograph is indicated for this specific substituted aniline.
• Role in pharmaceutical R&D/manufacturing (general)
  • May serve as an intermediate in the synthesis of API candidates or key fragments, providing a lipophilic, electron-donating aniline motif.
  • Can be derivatized to amides, ureas, sulfonamides, or heterocycles commonly evaluated in discovery programs.
• Handling considerations for GMP transitions
  • If used in regulated manufacturing as an intermediate, control residual levels per ICH Q3A/B and establish appropriate purge strategies.
  • Characterize potential nitrosamine risks when nitrosating agents are present; avoid co-presence of nitrite in acidic media except under tightly controlled lab conditions.

No therapeutic or clinical claims are made. This product is supplied strictly for research use, as noted in the Product Data.

Physical Properties

Item-specific specifications are not provided in the listing; use CoA for acceptance criteria. The following are literature/general expectations for this class of substituted anilines and this structure.

• Aggregate formula and mass (literature/computed)
  • Formula: C11H17N
  • Molecular weight: ~163.27 g/mol (computed)
• State/appearance
  • Not specified for this item; refer to CoA/Spec Sheet. Substituted anilines of similar size are commonly liquids or low-melting solids with characteristic amine odor (general).
• Acid–base properties (literature, typical for anilines)
  • pKa (conjugate acid, pKaH) expected ~4.8–5.5; electron-donating alkyl groups can slightly increase basicity versus aniline (pKaH ≈ 4.6).
• Partitioning and polarity (literature/estimates)
  • logP is expected to be higher than aniline (~0.9) due to n-butyl and methyl; approximate range 2.5–3.5 (general for para-alkyl anilines).
• Solubility (general trends)
  • Water: low at neutral pH due to hydrophobic substituents; solubility increases markedly upon protonation (e.g., as HCl salt).
  • Organic: miscible/soluble in alcohols, ethers, esters, chlorinated solvents, and aromatics (e.g., toluene); good solubility in polar aprotics (DMF, DMSO).
• Volatility/thermal behavior (literature expectations)
  • Boiling point likely in the 250–290 °C range at 1 atm for C11 anilines; reduced under vacuum (literature trend).
  • Refractive index for related para-alkyl anilines typically nD20 ~1.53–1.57.

All numerical values above are provided as literature/general expectations for closely related structures and are not item-specific specifications.

Quality and Grades

• Item-specific grade (from Product Data)
  • Grade/Purity: Reagent Grade.
• What “Reagent Grade” implies (general guidance)
  • Suitable for general laboratory synthesis and analytical sample preparation where high chemical purity is required but ultra-trace impurity control (e.g., LC–MS, semiconductor) is not mandatory.
  • Typical controls include identity confirmation and assay; impurity profiles (water, peroxides, metals, UV cutoffs) are not specified here. For acceptance limits, consult the CoA.
• Stabilizers/additives
  • Not specified for this item; refer to CoA/Spec Sheet. Many anilines are supplied neat without stabilizers; verify if any acid scavengers or antioxidants are present.
• Batch documentation
  • For each lot, request the CoA to confirm assay, residual solvents, and any tested parameters relevant to your method (e.g., GC area %, titratable amine content).
• Suitability notes
  • For moisture- or oxygen-sensitive applications (e.g., air-free coupling catalysis), you may wish to further dry or degas prior to use (see Reaction Conditions). If your analytical method is sensitive to trace basic impurities, verify via GC/HPLC.

Summary: This SKU provides a general laboratory grade suitable for most synthetic workflows. For specialized uses (chromatographic calibration, bioassays, trace analysis), verify fitness with your internal method and the lot-specific CoA.

Reaction and Applications

As a 2-methyl-4-n-butyl aniline, this molecule is a versatile nucleophilic/aromatic building block combining a basic aniline with hydrophobic alkyl substituents. Typical uses (literature/general):

• Protection and derivatization of the amine
  • Acylation to acetanilide carbamates/urethanes (Ac2O, Boc2O, CDI) to modulate directing effects and improve handling/crystallinity.
  • Sulfonylation (tosyl/mesyl) for directing-group or protecting-group strategies.
• Electrophilic aromatic substitution (EAS)
  • The –NH2 strongly activates the ring; remaining open positions (3,5,6) are ortho/para-directed. Existing 2-methyl/4-butyl substituents bias regioselectivity (3- and 5-substitution often favored).
  • Representative transformations: nitration (mild, temperature-controlled), halogenation, Friedel–Crafts acylation on the ring (with protected amine), formylation (Vilsmeier if protected).
• Diazotization and azo chemistry
  • Formation of the corresponding diazonium salt (NaNO2/HCl, 0–5 °C) enables azo coupling to phenols/anilines for dye/pigment intermediates; the bulky alkyl groups tune hydrophobicity.
• Cross-coupling and C–N bond formation
  • As a nucleophilic amine partner in urea/thiourea/carbamate formation and in C–N couplings (Buchwald–Hartwig, Chan–Lam with arylboronic acids on Cu). Protect if catalyst poisons.
• Heterocycle construction
  • Cyclization to benzimidazoles (with carbonyl equivalents), quinazolines/quinazolinones via condensation/oxidation sequences (when appropriately functionalized).
• Materials/ligand design
  • Hydrophobic, electron-donating arylamine motif is useful in OLED hole-transport segments, polymer intermediates, and as a lipophilic donor in small-molecule libraries.

Practical tips: pre-dry and, when needed, protect the amine to control EAS. For metal-catalyzed processes, use base and ligands tolerant to primary anilines; remove free amine or protect to avoid catalyst deactivation.

Reaction Conditions

Guidance below reflects general literature conditions for primary anilines with similar substitution; optimize for your substrate and scale.

• Acylation/protection
  • Ac2O or acyl chloride (1.1–1.5 eq) in DCM or toluene; base: pyridine or Et3N (1–2 eq); 0–25 °C, 0.5–2 h; typical isolated yields 85–98% (literature, protected anilines).
  • Boc protection: Boc2O (1.1–1.5 eq), DMAP catalytic, solvent: THF/MeCN; 20–25 °C, 1–4 h.
• Diazotization and azo coupling
  • 1–2 M HCl(aq), 0–5 °C; NaNO2 (1.05–1.2 eq) added dropwise; diazonium used in situ. Couple with activated aromatics in EtOH/aqueous base at 0–10 °C; typical conversions high; isolate as azo products.
• Electrophilic aromatic substitution
  • Halogenation: Br2 or NBS in AcOH/DCM; 0–25 °C; monitor to avoid polysubstitution. Nitration: HNO3 (dilute) in Ac2O or H2SO4 at 0–10 °C.
• Urea/carbamate formation
  • CDI (1.1–1.2 eq) in THF/DMF at 0–25 °C, then amine/ROH addition; or triphosgene/alternatives under controlled conditions (phosgene surrogates) with base.
• Buchwald–Hartwig amination (as nucleophile)
  • Aryl halide (1.0 eq), aniline (1.2–1.5 eq), Pd2(dba)3 or Pd(OAc)2 (0.5–2 mol%), bulky biaryl phosphine (e.g., XPhos/BrettPhos 1–4 mol%), base NaOtBu/K3PO4, solvent toluene/dioxane/2-MeTHF, 80–110 °C, 4–16 h; literature yields commonly 70–95% after optimization.
• Chan–Lam coupling
  • Arylboronic acid (1.5–2.0 eq), Cu(OAc)2 (5–20 mol%), base (pyridine or Et3N), solvent MeOH/EtOH or MeCN, air/O2, rt–50 °C, 6–24 h.

Notes: Primary anilines can poison catalysts; pre-form protected derivatives or adjust ligand/base. Maintain inert atmosphere for air-sensitive catalysts and ensure substrates are dry. Values above are literature guidance, not item-specific specs.

Safety and Handling

Item-specific GHS fields are not provided in the listing; defer to the product SDS for authoritative hazard, precautionary statements, and transport information.

• Item-specific hazard data
  • Signal word / H-statements / GHS classification / pictograms: Not specified for this item; refer to SDS.
• General hazards (aromatic primary amines; literature/good practice)
  • Harmful by inhalation, skin contact, or ingestion; may cause skin/eye irritation and respiratory irritation.
  • Aromatic amines can form N-oxides and undergo air oxidation/discoloration; minimize exposure to air/oxidants.
  • May cause methemoglobinemia upon significant exposure (general for anilines). Work in a fume hood.
• Handling guidance
  • Use in well-ventilated fume hood with appropriate PPE: lab coat, nitrile gloves (change regularly), splash goggles.
  • Avoid contact with strong oxidizers, acylating/alkylating agents unless intended; aromatic amines are nucleophilic.
  • Avoid prolonged skin contact; promptly wash with soap/water after handling.
• First-aid overview (consult SDS for full instructions)
  • Inhalation: move to fresh air, support breathing, seek medical attention.
  • Skin/eye: rinse with water for ≥15 minutes, remove contaminated clothing, obtain medical advice.
  • Ingestion: rinse mouth, do not induce vomiting, seek immediate medical attention.
• Fire and reactivity
  • Combustible organic; use CO2, dry chemical, or foam for small fires.
  • Thermal decomposition may generate toxic fumes (NOx). Store away from ignition sources.

Always consult and follow the SDS and institutional EHS policies before use.

Solvent Selection

This product is a hydrophobic aromatic amine building block, not a solvent. However, solvent choice critically affects its handling and reactivity.

• Polarity and solubility profile (general)
  • Moderately nonpolar with a basic amine. Readily soluble in ethers (THF, MTBE), aromatics (toluene, xylene), chlorinated solvents (DCM, DCE), esters (EtOAc), and polar aprotics (DMF, DMAc, NMP, DMSO). Low aqueous solubility at neutral pH; high solubility in acidic aqueous media as its ammonium salt.
• Dielectric constant and miscibility (by solvent)
  • For nucleophilic aromatic substitutions or metal-catalyzed couplings, polar aprotics (DMF/DMAc/NMP, ε ~37–47; DMSO, ε ~47) can enhance rates.
  • For electrophilic aromatic substitution or acylations, toluene or DCM provide good solubility and manageable reactivity.
• Choosing among common media (practical tips)
  • Protecting group manipulations (acetylation, carbamates): DCM or toluene with base (pyridine, Et3N).
  • Diazotization/azo coupling: aqueous mineral acid for diazotization (0–5 °C), then couple in ethanol/ACN or mixed aqueous/organic systems.
  • Buchwald–Hartwig or urea formation: toluene, dioxane, or tBuOH for Pd-catalysis; DMF/DME for SNAr or CDI-mediated couplings.
• Comparison notes
  • Toluene vs DCM: toluene offers higher boiling point and greener profile; DCM enables lower-temperature control but with higher EH&S burden.

Select solvents that balance solubility, reaction rate, and downstream workup, and verify catalyst/base compatibility with a primary aniline.

Storage and Reconstitution

• Storage (from Product Data)
  • Store at room temperature.
• Container and atmosphere (general best practice for anilines)
  • Keep tightly closed in amber glass to minimize light exposure and oxidative discoloration. For long-term storage, consider an inert headspace (N2/Ar) and store desiccated.
• Stability notes
  • Aromatic amines may slowly darken on air exposure due to oxidation; this typically does not affect performance but monitor assay and color. If significant discoloration occurs, consider purification (e.g., distillation under reduced pressure or column after protection) prior to critical use.
• Reconstitution
  • Supplied neat; no reconstitution required. If preparing stock solutions, use dry, oxygen-limited solvents (e.g., toluene, THF, MeCN) and store in sealed vials at 2–8 °C when practical. Avoid acidic stock solutions unless forming a defined salt for aqueous work.
• Shipping
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Always refer to the lot-specific CoA and SDS for definitive storage and handling instructions. Research use only, as noted in the Product Data.

Structure and Identity

A para-butyl, ortho-methyl substituted aniline (aromatic primary amine) useful as a hydrophobic aniline building block.

• Item-specific identifiers (from Product Data)
  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identity data (general reference)
  • Molecular formula: C11H17N (literature)
  • Molecular weight: ~163.27 g/mol (computed from C11H17N)
• Structural features (general description)
  • Core: benzene ring bearing a primary amine (–NH2) at position 1 (aniline).
  • Substituents: methyl at C2 (ortho to –NH2) and n-butyl at C4 (para to –NH2).
  • Functional groups: aromatic amine (basic), hydrophobic alkyl substituents (methyl, n-butyl).
  • Regiochemistry: 2-methyl/4-butyl relative to the –NH2 director; remaining unsubstituted ring positions are 3,5,6.
  • Stereochemistry: none (achiral). 2D depiction would show –NH2 on the ring, a small methyl at the adjacent ortho carbon, and a linear n-butyl chain para to the amine.
• Synonymy notes (general)
  • Also described as 2-methyl-4-n-butylaniline; “o-methyl, p-n-butyl aniline.”

Note: Exact registry identifiers (CAS, InChIKey, specific SMILES) are not provided in the item record and should be confirmed against the product’s CoA/Specification Sheet for this SKU (B483595).

Synthetic Utility

Key reactivity arises from the primary aniline and an activated aromatic ring bearing ortho/para-directing, electron-donating substituents.

• Functional group handles
  • Primary aniline: nucleophilic at N; allows acylation, carbamoylation, sulfonylation, urea formation, imine/Schiff base formation, reductive amination (of carbonyls), and diazotization.
  • Aromatic ring: strongly activated toward EAS; substitution patterns guided by –NH2, with existing 2-Me and 4-nBu modulating sterics/regioselectivity.
• Named transformations (literature)
  • Buchwald–Hartwig C–N coupling (as N-nucleophile partner).
  • Chan–Lam amination with arylboronic acids.
  • Sandmeyer-related sequences via diazonium salts (for installing Cl/Br/CN, etc., if desired from diazo stage).
  • Vilsmeier–Haack (on protected aniline) for ring formylation.
  • Mills reaction/azo coupling after diazotization.
• Retrosynthetic value
  • Serves as a convergent node: N-derivatization yields diverse amides/ureas; ring substitution enables rapid SAR around a lipophilic aniline core; diazonium chemistry enables late-stage diversification.
• Practical considerations
  • Protect –NH2 (e.g., Ac, Boc) to suppress over-activation during EAS or to avoid catalyst poisoning in metal-catalyzed couplings.
  • Use non-nucleophilic bases (DIPEA, NaOtBu) where needed; control temperature to maintain selectivity given the activated ring.

This balance of nucleophilicity (at N) and ring activation makes the reagent a versatile entry point to hydrophobic, electron-rich arylamine derivatives.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent (aromatic amine), not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype applies. Item-specific target data: Not specified for this item; refer to CoA/Spec Sheet if any application testing is provided.