3034-55-7

Basic information

• Product Name: 5-Bromothiazole
• Synonyms: 5-Bromo-1,3-thiazole, tech;5-BroMothiazole 95%;5-Bromo-1,3-thiazole,97%;5-BROMOTHIAZOLE;Thiazole, 5-bromo-;5-BROMOTHIAZOLE,98%
• CAS NO: 3034-55-7
• Molecular Formula: C₃H₂BrNS
• Molecular Weight: 164.02
• Product Categories: Heterocyclic Building Blocks;ThiazolesHeterocyclic Building Blocks;Building Blocks;API;Thiazoles;Thiazole;Building Blocks;Halogenated Heterocycles
• Mol File: 3034-55-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 131-132 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 80-81°C/18mm
• Flash Point: 170°F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.835
• Vapor Pressure: 0.535mmHg at 25°C
• Refractive Index: 1.5955
• PKA: 1.00±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 5-Bromothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromothiazole(3034-55-7)
• EPA Substance Registry System: 5-Bromothiazole(3034-55-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41-43
• Safety Statements: 26-36/37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 3034-55-7(Hazardous Substances Data)

Usage

Uses

5-Bromothiazole is used as a pharmaceutical intermediate and performance material.

General Description

5-Bromothiazole is a monobromothiazole, which can be prepared via treatment of 2,5-dibromothiazole with sodium ethoxide followed by hydrogenation over spongy nickel.

Purification Methods

If bromothiazole is too coloured, then suspend it in dilute NaOH and steam distil it. Add NaCl to the aqueous distillate, extract it with Et2O, dry it (Na2SO4), evaporate and fractionate the residue in a vacuum. The HgCl2 salt crystallises from EtOH with m 148o (dec). [Beyerman et al. Recl Trav Chim, Pays Bas 73 330 1954, Beilstein 27 III/IV 962.]

InChI:InChI=1/C3H2BrNS/c4-3-1-5-2-6-3/h1-2H

Upstream product

• 4175-78-4 2,5-dibromo-1,3-thiazole 
• 288-47-1 1,3-thiazole 
• 79265-30-8 2-(trimethylsilyl)thiazole 
• 3034-22-8 5-bromo-2-aminothiazole 

Downstream Products

• 14527-41-4 thiazole-5-carboxylic acid 
• 14542-14-4 5-Methoxy-thiazol 
• 25115-63-3 5-Ethoxythiazol 
• 774230-98-7 1-(5-bromo-1,3-thiazol-2-yl)ethanone 
• 1175534-98-1 5-(2-nitrophenyl)thiazole 
• 602298-91-9 5-(3-methoxyphenyl)thiazole 
• 859481-13-3 5‐(3‐nitrophenyl)‐1,3‐thiazole 

Relevant articles and documents

Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods

The synthesis of the full family of bromothiazoles has been revisited in order to update and optimize their production. The species reported include 2-bromothiazole, 4-bromothiazole, 5-bromothiazole, 2,4-dibromothiazole, 2,5-dibromothiazole, 4,5-dibromothiazole, and 2,4,5-tribromothiazole, the majority of which are produced via sequential bromination and debromination steps. This complete family can now be produced without the use of elemental bromine, and the presented methods have allowed the physical and NMR spectroscopic characterization of the full family to be reported for the first time.

HETEROCYCLYL-SUBSTITUTED ANTI-HYPERCHOLESTEROLEMIC COMPOUNDS

This invention provides cholesterol absorption inhibitors of Formula I: and the pharmaceutically acceptable salts thereof, wherein R12 is a hydroxylated alkyl group and R9 contains a heterocyclic ring. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating atherosclerosis and preventing atherosclerotic disease events.

COURSE OF BROMINATION OF THIAZOLE AND 2-METHYLTHIAZOLE

Bromination of thiazole by bromine in the presence of aluminium chloride in neutral solvent or without solvent takes place at the 2-position.Such an orientation contradicts the traditional addition-cleavage mechanism, and agrees with the ylid mechanism of electrophilic substitution. 2-Methylthiazole brominates at the 5-position, and the reaction is impeded in the presence of aluminium chloride; this is due to heterocycle deactivation by complexation with the Lewis acid at the nitrogen atom.