This compound belongs to the class of organic compounds known as 2,5-disubstituted thiazoles. These are compounds containing a thiazole ring substituted at positions 2 and 5 only.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Not applicable. No validated bioassay, immunoassay, or imaging protocols are provided for this small-molecule building block.
General handling suggestions for solution preparation (non-binding guidance):
Prepare stock solutions in anhydrous DMSO or DMF (e.g., 10–100 mM) under inert atmosphere. Filter (0.2 μm PTFE) if necessary.
For aqueous use, convert to a defined salt (e.g., HCl) to improve solubility, or use co-solvent systems. Confirm pH and compatibility with your assay components.
Biological Roles
Item-specific biological data are not provided. The material is supplied strictly for research use.
General context (biochemistry/medicinal chemistry literature):
Thiazole motif: prevalent in bioactive molecules, including natural products (e.g., thiamine/vitamin B1 contains a thiazolium core) and numerous synthetic kinase inhibitors, antimicrobials, and agrochemicals. The thiazole ring is π-deficient and can modulate H-bond basicity and dipole orientation in ligands.
Primary amines: frequently used as cationic anchors in ligand design; at physiological pH, the –CH2NH2 group is largely protonated (pKaH typically ~9–10 for aliphatic amines), enabling ionic interactions with acidic residues in protein active sites.
Substituted-thiazoles: C2-functionalization profoundly influences electronics and heteroatom orientation, impacting target engagement and metabolic stability.
No claims are made regarding biological activity, efficacy, or safety of this specific compound. Any biological testing should be conducted under appropriate institutional approvals and safety oversight.
Buffer Applications
This product is not a buffering agent and is not typically used to prepare defined pH buffers.
Practical notes:
The primary amine can be protonated to form water-soluble salts (e.g., hydrochloride) to facilitate aqueous handling or extractions, but such solutions are not buffers and have poor buffering capacity compared to dedicated systems.
For workups or bioconjugation, pair with standard buffers (e.g., phosphate, HEPES) as appropriate to your system.
For robust buffer systems and recipes, consult dedicated buffering reagents.
Green Alternatives
While many transformations on this scaffold are traditionally run in DMF, NMP, dioxane, or chlorinated solvents, greener choices are viable with appropriate condition optimization.
Greener solvent swaps (literature/general):
Replace DMF/NMP with Cyrene, propylene carbonate, or dimethyl carbonate where solubility and reactivity permit (e.g., some acylations, SNAr).
Substitute dioxane/THF with 2-MeTHF or CPME for cross-couplings; often compatible with Pd catalysts and bases, offering improved safety and lower peroxide risk vs THF.
Use ethanol or isopropanol for reductive aminations, with solid-supported catalysts when feasible.
Catalysis and reagents:
Employ ligand-efficient Pd systems (e.g., XPhos/SPhos-derived precatalysts) at low loadings; explore Ni catalysis for arylation to reduce cost and Pd footprint.
For amine acylations, use green coupling reagents (e.g., CDI) or enzymatic acylations in benign media when compatible.
Workup/waste minimization:
Form crystalline salt intermediates (e.g., HCl salt) for purification by filtration rather than chromatography.
Apply aqueous micellar catalysis (TPGS-750-M) for certain couplings and acylations to reduce organic solvent usage.
Trade-offs:
Solubility constraints in greener media may require co-solvents or higher temperatures.
Catalyst/ligand performance can be solvent-dependent; small-scale scouting is recommended before scale-up.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation specifications are provided for this item.
General context (process chemistry/med-chem):
2-chloro-thiazoles are common intermediates in the synthesis of heteroaromatic fragments for lead optimization campaigns.
The aminomethyl handle enables rapid diversification via amide/sulfonamide libraries and linkage to solid supports or tags.
This product is supplied for research use only and is not intended for human or veterinary use, nor for clinical or diagnostic applications.
Physical Properties
Item-specific physicochemical specifications (bp, mp, density, refractive index, pKa, logP, solubility): Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for this structural class (for planning only):
State/appearance: small heteroaromatic amines are often low-melting solids or high-boiling oils (literature, compound-class expectation).
Basicity: primary alkyl amines typically have pKaH ~9–10 (literature, for ammonium conjugate acid), implying the free base is protonated under mildly acidic conditions and can form water-soluble salts (e.g., HCl, H2SO4 salts).
Polarity/solubility: such thiazolyl amines are commonly soluble in polar aprotic solvents (DMSO, DMF, NMP) and alcohols; limited solubility in nonpolar hydrocarbons (literature, class behavior). Salt forms are water-soluble (literature).
Volatility: reduced relative to nonpolar aromatics due to heteroatoms and hydrogen bonding (literature).
Note: Use these generalities only for preliminary method development. Always confirm exact properties of this lot from the CoA/Spec Sheet and SDS before scale-up or formulation.
Quality and Grades
Grade/purity for this specific catalog item: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance):
Research grade: suitable for most synthetic applications; typical impurity profiles not intended for clinical use.
≥95–98% purity (often stated for building blocks): adequate for discovery chemistry; may require purification for sensitive transformations (e.g., cross-couplings) if trace bases or halide impurities are detrimental.
HPLC/LCMS traceable: when provided, implies tighter control on UV-absorbing impurities; useful for medicinal chemistry.
Considerations specific to this scaffold:
Aryl chloride at C2: trace hydrolysis or dehalogenation can reduce coupling efficiency; review CoA for halogen assay if available.
Primary amine: can form salts; confirm free-base vs. salt form on the CoA (affects molecular weight, solubility, and stoichiometry). Stabilizers are not typically used for such amines; if any stabilizer is present, it will be stated on the CoA.
Recommendations:
For Pd-catalyzed couplings, consider a short pre-purification (plug or recrystallization) if the CoA shows borderline purity or if reactions stall.
Retain CoA/Spec Sheet with your batch for regulatory or reproducibility documentation.
Reaction and Applications
This bifunctional thiazole is valuable in heterocycle elaboration, enabling orthogonal chemistry at C2 and on the aminomethyl side chain.
Cross-coupling at C2–Cl: Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig (post-halide activation), Stille, or Negishi couplings to introduce aryl, vinyl, or alkyl groups. The thiazole ring’s π-deficiency activates C2 toward oxidative addition; amine protection (Boc, Cbz) is recommended to prevent catalyst inhibition.
Metal–halogen exchange: i-PrMgCl·LiCl (Turbo Grignard) or n-BuLi at low temperature can generate C2-thiazolyl metals for electrophile trapping (acylation, formylation, borylation). Control temperature to avoid ring lithiation elsewhere.
Nucleophilic elaboration of –CH2NH2: acylation (amides), sulfonylation (sulfonamides), carbamate formation, urea synthesis, reductive alkylation, or quaternization to ammonium salts.
Salt formation: conversion to hydrochloride or other mineral acid salts to improve handling, crystallinity, and aqueous workups.
Conjugation handles: –CH2NH2 couples with activated esters (NHS), isocyanates, or carbonates for linker installation.
Practical tips:
Protect the amine during C2 cross-coupling to reduce off-cycle binding; deprotect under mild conditions afterward.
Maintain anhydrous, oxygen-free conditions (argon) to suppress hydrolysis/oxidation; aligns with the item’s storage guidance.
If competing N-arylation is observed, adjust ligand/base or employ transient amine protection.
Reaction Conditions
The following are representative literature-style conditions for analogous thiazolyl systems and should be used as general guidance only. Optimize for your substrate and scale.
Suzuki–Miyaura coupling at C2–Cl:
Conditions: Pd(dppf)Cl2·DCM (2–5 mol%), K2CO3 or Cs2CO3 (2–3 equiv), 1,4-dioxane/H2O (3:1) or 2-MeTHF/H2O, 80–100 °C, 4–16 h.
Notes: Protect –CH2NH2 (e.g., Boc) to minimize catalyst inhibition. Alternative ligands: SPhos/XPhos for challenging partners.
Buchwald–Hartwig amination (if converting C2–Cl to C2–NR):
Pd2(dba)3 (1–2 mol%), BrettPhos or RuPhos ligand (2–4 mol%), NaOtBu (2–3 equiv), toluene or t-BuOH, 80–100 °C, 6–20 h.
Halogen–metal exchange at C2:
i-PrMgCl·LiCl (2.0 equiv) in THF, −40 to 0 °C, then electrophile (e.g., DMF for formylation) followed by quench; or n-BuLi (1.1–1.5 equiv) at −78 °C for more reactive exchanges. Keep –CH2NH2 protected to avoid acid–base side reactions.
Reductive amination on –CH2NH2:
Aldehyde (1.2–2.0 equiv), AcOH (cat.), MeOH or EtOH, then NaBH3CN (1.5–2.0 equiv) at rt to 40 °C, 2–6 h; or H2 (1–3 bar), Pd/C (5–10 wt%) in EtOH.
Acylation/sulfonylation:
Acyl chloride/sulfonyl chloride (1.1–1.5 equiv), DIPEA or TEA (2–3 equiv), DCM or THF, 0 °C → rt, 1–3 h.
Yields are substrate- and condition-dependent; consult primary literature for closely related examples.
Safety and Handling
GHS classification, signal word, H-statements, and pictograms: Not specified for this item; refer to SDS.
General laboratory safety for heteroaromatic primary amines and aryl chlorides (non-authoritative; for planning):
Likely hazards: skin/eye irritation, respiratory irritation; amines can be sensitizers/irritants. Avoid inhalation and contact.
PPE: lab coat, safety glasses or face shield, nitrile gloves; change gloves regularly. Handle in a chemical fume hood.
Storage incompatibilities: segregate from strong oxidizers, acid chlorides/anhydrides (uncontrolled acylation), and strong acids/bases unless forming a controlled salt. Avoid moisture and air exposure per item storage guidance.
Special risks: primary amines can absorb CO2 and moisture; heteroaromatic chlorides may hydrolyze slowly under strongly basic, wet conditions. Protect from light as specified.
First aid (overview; defer to SDS): rinse skin/eyes with water for at least 15 minutes upon contact; seek medical attention. If inhaled, move to fresh air. If ingested, do not induce vomiting; seek medical attention.
Manufacturer storage guidance (authoritative for this item):
Store at −20 °C, protected from light, under argon (inert atmosphere).
Shipped cold (ice chest + ice pads) to maintain material integrity.
Always consult the official SDS for definitive hazard and response information.
Solvent Selection
Applicability: This product is a small, heteroaromatic primary amine with an activated aryl chloride. Solvent choice depends on whether you are exploiting the C2–Cl electrophile (e.g., metal-catalyzed coupling) or the –CH2NH2 nucleophile.
General solvent behavior (literature/class-based):
Polar aprotic (DMSO, DMF, NMP): high solubility for both free base and many salts; ideal for coupling and SNAr; good for stock solutions.
Alcohols (MeOH, EtOH, i-PrOH): moderate to good solubility; useful for salt formation, reductive amination, and acylations.
Ethers (THF, 2-MeTHF, CPME): variable solubility; often paired with a polar co-solvent or base for metalation/couplings.
Water: free base has low solubility; salt forms (e.g., HCl) are water-soluble.
Selection tips by transformation:
Cross-coupling at C2–Cl: toluene/1,4-dioxane/THF with polar co-solvent (DMF or t-BuOH) under Pd catalysis; ensure amine protection to avoid catalyst poisoning.
Functionalizing –CH2NH2: conduct acylations/sulfonylations in DCM, THF, or acetonitrile with a base (DIPEA, TEA); reductive aminations in MeOH/EtOH or MeCN with NaBH3CN or H2/Pd.
Note: These are general guidelines. Verify actual solubility and stability of this specific lot experimentally; item-specific solubility is not provided here.
General reconstitution and handling (planning guidance; verify with CoA/SDS):
Open containers under inert atmosphere if possible. Minimize exposure to air and moisture.
For stock solutions, use anhydrous solvents (e.g., DMSO, DMF, acetonitrile, 2-MeTHF) based on your intended application. Item-specific solubility is not provided; determine empirically on small scale.
If aqueous handling is required, consider forming a defined salt (e.g., hydrochloride) to improve solubility and stability.
Aliquot solutions to avoid repeated freeze–thaw. Store solutions at −20 °C under inert gas and protected from light; monitor for degradation by LC/MS or HPLC.
Shelf life and stability: Not specified for this item; refer to CoA/Spec Sheet.
Always follow your institution’s chemical hygiene plan and consult the SDS for detailed stability and incompatibility information.
Structure and Identity
A thiazole heteroaromatic bearing a chloride at the 2-position and an aminomethyl substituent at the 5-position; useful as a bifunctional building block (electrophilic C2–Cl and nucleophilic –CH2NH2).
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general description):
Core ring: thiazole (five-membered, aromatic), containing one ring nitrogen and one ring sulfur.
Substitution pattern: chlorine at C2 (adjacent to both N and S), and –CH2NH2 at C5.
Functional groups: aryl chloride (on an electron-deficient thiazole carbon), primary aliphatic amine (basic, nucleophilic), heteroaromatic ring (π-deficient relative to benzene).
Stereochemistry: none (achiral molecule).
Reactivity handles: C2–Cl is activated toward metal–halogen exchange and cross-coupling; the aminomethyl can be protected (e.g., Boc, Cbz) or transformed (acylation, sulfonylation, reductive alkylation).
Synthetic Utility
Key functional handles and their typical reactivity (literature/general):
Derivatization: acylation (amides), sulfonylation, carbamates, ureas/thioureas; reductive alkylation with aldehydes/ketones.
Quaternization and salt formation to modulate solubility/physical properties.
Strategic value:
Orthogonal chemistry: protect the amine to unlock C2 coupling; deprotect late-stage to functionalize side-chain.
Vector exploration: varying C2 substituents tunes electronics and topology while retaining the –CH2NH2 for target engagement or linker installation.
Library synthesis: amenable to parallel synthesis workflows using solid-supported scavengers for rapid purification.
Target Specificity
Not applicable. This product is a small-molecule heterocycle, not an antibody, enzyme, or biologic. No target, clone, isotype, or species reactivity information is associated with this item.
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