Thiazole

Base Information

• Chemical Name: Thiazole
• CAS No.: 288-47-1
• Deprecated CAS: 857224-45-4
• Molecular Formula: C3H3NS
• Molecular Weight: 85.1295
• Hs Code.: 29341000
• European Community (EC) Number: 206-021-3
• UN Number: 1993
• UNII: 320RCW8PEF
• DSSTox Substance ID: DTXSID2059776
• Nikkaji Number: J26D
• Wikipedia: Thiazole
• Wikidata: Q413426
• Metabolomics Workbench ID: 44003
• ChEMBL ID: CHEMBL15605
• Mol file: 288-47-1.mol

Synonyms:Thiazole;Thiazoles

Chemical Property of Thiazole

Chemical Property:

• Appearance/Colour: colourless or pale yellow liquid
• Vapor Pressure: 21.6mmHg at 25°C
• Melting Point: -33 °C
• Refractive Index: n20/D 1.538(lit.)
• Boiling Point: 116.5 °C at 760 mmHg
• PKA: 2.44(at 20℃)
• Flash Point: 26 ºC
• PSA: 41.13000
• Density: 1.18 g/cm³
• LogP: 1.14310
• Storage Temp.: Flammables area
• Sensitive.: Air & Light Sensitive
• Water Solubility.: slightly soluble
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 84.99862027
• Heavy Atom Count: 5
• Complexity: 30.1
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

Thiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F
• Hazard Codes: Xn,F
• Statements: 10-22-37/38-41
• Safety Statements: 16-26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Thiazoles
• Canonical SMILES: C1=CSC=N1
• Uses: Thiazole is used as a flavoring agent and in the preparation of dyes and rubber accelerators. It serves as a component of the vitamin thiamine (B1). It acts as a protected formyl group used in natural product synthesis. It reacts with alkyl lithium and Grignard?s reagent to prepare organometallic complexes. It is involved in the electrophilic aromatic substitution and nucleophilic aromatic substitution at C-5 and C-2 positions respectively. Further, it undergoes alkylation reaction to get thiazolium cation, which is used as a catalyst in the Stetter reaction and the Benzoin condensation. In addition to this, it is involved in the preparation of alagebrium. Thiazoles were used to create novel recognition motifs for interaction with divalent and trivalent metal ions in siderophores or antibiotics. Organic synthesis of fungicides, dyes, and rubber accelerators.

Technology Process of Thiazole

There total 66 articles about Thiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2,3:5,6-Di-O-isopropylidene-1-(2-thiazolyl)-α-D-mannofuranose (160701-79-1) → 1,3-thiazole (288-47-1) + 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone (7306-64-1,14440-56-3,23262-80-8,27108-15-2,49561-21-9,67642-42-6)

Guidance literature:

With 4 A molecular sieve; In toluene; at 130 ℃; for 14h; Product distribution; Mechanism; elimination of thiazole from thiazolylketofuranoses and -ketopyranoses; no reaction with 1-O-acetyl and 1-O-trimethylsilyl derivatives, thiazolyl alcohols; no elimination of furyl- and thienyl-group;

DOI:10.3987/COM-98-8154

Reference yield: 92.0%

2,5-dibromo-1,3-thiazole (4175-78-4) → 1,3-thiazole (288-47-1)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In methanol; at 23 ℃; for 12h;

DOI:10.1080/00397919508011485

Reference yield: 91.0%

4-bromo-1,3-thiazole (34259-99-9) → 1,3-thiazole (288-47-1)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In methanol; at 23 ℃; for 12h;

DOI:10.1080/00397919508011485

upstream raw materials:

1,4-dithiane-2,5-diol

formaldehyd

2-chlorothiazole

2,2-diethoxy-1-formylaminoethane

Downstream raw materials:

1-(1,3-thiazol-2-yl)cyclobutanol

thiazole-2-sulfonyl chloride

2-[1-(5-fluoro-3-(naphth-2-ylmethoxy)phenyl)propyl]thiazole

(1,3-thiazol-2-yl)methanol

Refernces

• 1、 Brandsma, L.,Jong, R. L. P. de,VerKruijsse, H. D.. "An Efficient Synthesis of 1,3-Thiazole". . p. 948 - 949. Retrieved 1985.
• 2、 -. "PYRAZINE DERIVATIVE AND APPLICATION THEREOF IN INHIBITING SHP2". . . Retrieved 2022/01/23.
• 3、 Ueno, Ryota,Shimizu, Takashi,Shirakawa, Eiji. "Reduction of Aryl Halides into Arenes with 2-Propanol Promoted by a Substoichiometric Amount of a tert-Butoxy Radical Source". supporting information. p. 741 - 744. Retrieved 2016/03/12.