7238-61-1

Basic information

• Product Name: 2-Bromo-4-methylthiazole
• Synonyms: 2-Bromo-4-methyl-1,3-thiazole;2-Bromo-4-methylthiazole;Thiazole, 2-bromo-4-methyl-;2-Bromo-4-Methylthiazole ada@tuskwei.com sky
• CAS NO: 7238-61-1
• Molecular Formula: C₄H₄BrNS
• Molecular Weight: 178.05
• EINECS: 1533716-785-6
• Product Categories: Halides;Thiazoles, Isothiazoles &Benzothiazoles;Thiazoles;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;Thiazole;C3 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;2-Bromo-4-Methylthiazole ada@tuskwei.com sky;18031153937@189.cn
• Mol File: 7238-61-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 195.1 °C at 760 mmHg
• Flash Point: 90°C
• Appearance: /
• Density: 1.654g/mLat 25℃
• Vapor Pressure: 3.52E-18mmHg at 25°C
• Refractive Index: n20/D 1.572
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 1.36±0.10(Predicted)
• Sensitive: Stench
• CAS DataBase Reference: 2-Bromo-4-methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-methylthiazole(7238-61-1)
• EPA Substance Registry System: 2-Bromo-4-methylthiazole(7238-61-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 7238-61-1(Hazardous Substances Data)

Usage

Uses

2-Bromo-4-methylthiazole is a useful reagent for preparing galactoside inhibitor of galectins.

InChI:InChI=1/C11H13IN4O3/c12-5-2-16(8-1-6(18)7(3-17)19-8)11-9(5)10(13)14-4-15-11/h2,4,6-8,17-18H,1,3H2,(H2,13,14,15)

Upstream product

• 693-95-8 4-Methylthiazole 
• 1603-91-4 4-methylthiazol-2-ylamine 
• 3029-48-9 thiocyanoacetone 

Downstream Products

• 515-59-3 sulfamethylthiazole 
• 71119-13-6 N-(4-{[(4-methyl-2-thiazolyl)amino]sulfonyl}phenyl)-acetamide 
• 1217864-20-4 C₂₂H₂₄F₄N₄OS 
• 138330-01-5 4-(4-methyl-thiazol-2-yl)-phenol 
• 145464-54-6 4-(4-methylthiazol-2-yl)benzonitrile 

Relevant articles and documents

Improved procedure for the synthesis of thiazolium-type peptide coupling reagents: BMTB as a new efficient reagent

An efficient scalable synthesis of 2-halothiazolium-type peptide coupling reagents has been developed. The key step is the formation of the 2-bromothiazole scaffold through cyclization of α-thiocyanato ketones with hydrogen bromide. Using this method, the new coupling reagent 2-bromo-N-methylthiazolium bromide (BMTB) was synthesized. BMTB was tested in a difficult model coupling reaction of two sterically hindered N-methylated amino acids and showed higher activity than the well-established peptide coupling reagent HATU.

A novel thiazolium type peptide coupling reagent for hindered amino acids

A highly efficient coupling reagent, 2-bromo-3-ethyl-4-methyl thiazolium tetrafluoroborate (BEMT), was designed, synthesized and successfully applied to the synthesis of oligopeptides containing N-alkyl or α-C-dialkyl amino acids. Its efficiency was evaluated by HPLC and 1H NMR methods, and demonstrated by synthesis of a number of N-methyl-rich peptide segments with good yields and negligible racemization. The mechanism of coupling was studied by HPLC, 1H NMR and IR monitoring; it is proposed that labile (acyloxy)thiazolium salts and N-protected amino acid bromides were the major active intermediates with concomitant formation of N-ethyl-4-methyl thiazolidones and a small amount of oxazolones and N-protected amino acid anhydrides.