Description

1,3-Thiazol-4-ylboronic acid (CAS No. 1016642-07-1) is a high-purity boronic acid derivative featuring a thiazole heterocycle, making it a valuable building block for Suzuki-Miyaura cross-coupling reactions. With the molecular formula C₃H₄BNO₂S and a molecular weight of 128.94 g/mol, this compound is ideal for pharmaceutical, agrochemical, and materials science research. Its boronic acid moiety enables efficient C-C bond formation, while the thiazole ring contributes to diverse biological activity and coordination chemistry. Supplied as a white to off-white crystalline powder, it is rigorously tested for purity (typically ≥95% by HPLC) and stability under recommended storage conditions (2-8°C under inert atmosphere). Compatible with organic solvents like DMF, THF, and DMSO, this reagent is essential for medicinal chemistry, ligand design, and functional material synthesis.

Properties

• CAS Number: 1016642-07-1
• Complexity: 81.7
• IUPAC Name: thiazol-4-ylboronic acid
• InChI: InChI=1S/C3H4BNO2S/c6-4(7)3-1-8-2-5-3/h1-2,6-7H
• InChI Key: WSTDOIHBEOVTHX-UHFFFAOYSA-N
• Exact Mass: 129.0055797
• Molecular Formula: C3H4BNO2S
• Molecular Weight: 128.95
• SMILES: B(C1=CSC=N1)(O)O
• Topological: 81.6
• Monoisotopic Mass: 129.0055797
• Synonyms: 1016642-07-1, 1,3-thiazol-4-ylboronic acid, DTXSID40670302, DTXCID40621051, 847-480-5, thiazol-4-ylboronic acid, Boronic acid, B-4-thiazolyl-, THIAZOLE-4-BORONIC ACID, (1,3-THIAZOL-4-YL)BORONIC ACID, Thiazol-4-ylboronicacid, MFCD09879002, 2-Thiazole-4-boronic acid, SCHEMBL243089, WSTDOIHBEOVTHX-UHFFFAOYSA-N, AKOS006312360, AB54186, PS-12975, DB-058635, DB-328748, CS-0175107, EN300-246731, P19194

Application

1,3-Thiazol-4-ylboronic acid is widely used in Suzuki-Miyaura cross-coupling reactions to introduce the thiazole moiety into biaryl systems for drug discovery. It serves as a key intermediate in synthesizing kinase inhibitors, antimicrobial agents, and fluorescent probes due to the thiazole’s electron-rich properties. Researchers also employ it to construct metal-organic frameworks (MOFs) and conjugated polymers for optoelectronic applications.

Safety and Hazards

GHS Hazard Statements

• H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (66.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (33.3%)
• Skin Irrit. 2 (66.7%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (66.7%)

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