2-Bromothiazole

2-Bromothiazole
  • CAS No.:3034-53-5
Other grades of this product :
2-Bromothiazole Chemical Properties
Melting point 171 C
Boiling point 171 °C (lit.)
density 1.82 g/mL at 25 °C (lit.)
refractive index n20/D 1.593(lit.)
Fp 146 °F
storage temp. 2-8°C
solubility Chloroform, Dichloromethane
pka0.84±0.10(Predicted)
form Liquid
color Clear colorless to orange-brown
Specific Gravity1.836
Water Solubility insoluble
BRN 105724
InChIKeyRXNZFHIEDZEUQM-UHFFFAOYSA-N
CAS DataBase Reference3034-53-5(CAS DataBase Reference)
NIST Chemistry ReferenceThiazole, 2-bromo-(3034-53-5)
EPA Substance Registry SystemThiazole, 2-bromo- (3034-53-5)
Safety Information
Hazard Codes Xi,F
Risk Statements 36/37/38
Safety Statements 23-24/25-36-26
RIDADR 1993
WGK Germany 3
TSCA Yes
HazardClass IRRITANT, FLAMMABLE
HS Code 29341000
MSDS Information
ProviderLanguage
2-Bromo-1,3-thiazole English
SigmaAldrich English
ACROS English
ALFA English
2-Bromothiazole Usage And Synthesis
DescriptionIt is usually used as the intermediate or raw material to produce various products in the organic synthesis and pharmaceutical industry, such as 2-acetylthiazole, antibiotics, and anticholinergic drugs. Specifically, this chemical can act as the raw material to produce camalexin through reaction with indolylmagnesium iodide.1 Moreover, this substance has been selected as the reactant to prepare the thiazole Grignard reagents and thiazolyllithium compounds, which can be converted into thiazole-2-carboxylic acid via a halogen-metal exchange reaction.2, 3 In addition, 2-bromothiazole has been used to synthesize N-aryl aminothiazoles, which are found to function as the inhibitors of cyclin-dependent kinases.4 Besides, this compound may be involved in the synthesis of ethynylthiazoles that exhibits a desirable anti-inflammatory activity.5
Referrence
  1. Ayer, W. A.; Craw, P. A.; Ma, Y. T.; Miao, S. C., SYNTHESIS OF CAMALEXIN AND RELATED PHYTOALEXINS. Tetrahedron 1992, 48, 2919-2924.
  2. Kurkjy, R. P.; Brown, E. V., THE PREPARATION OF THIAZOLE GRIGNARD REAGENTS AND THIAZOLYLLITHIUM COMPOUNDS. J. Am. Chem. Soc. 1952, 74, 6260-6262.
  3. Beyerman, H. C.; Berben, P. H.; Bontekoe, J. S., THE SYNTHESIS OF THIAZOLE-2-CARBOXYLIC AND OF THIAZOLE-5-CARBOXYLIC ACID VIA A HALOGEN-METAL EXCHANGE REACTION. Recl. Trav. Chim. Pays-Bas-J. Roy. Neth. Chem. Soc. 1954, 73, 325-332.
  4. Misra, R. N.; Xiao, H. Y.; Williams, D. K.; Kim, K. S.; Lu, S. F.; Keller, K. A.; Mulheron, J. G.; Batorsky, R.; Tokarski, J. S.; Sack, J. S.; Kimball, D.; Lee, F. Y.; Webster, K. R., Synthesis and biological activity of N-aryl-2-aminothiazoles: potent pan inhibitors of cyclin-dependent kinases. Bioorg. Med. Chem. Lett. 2004, 14, 2973-2977.
  5. Geronikaki, A.; Vasilevsky, S.; Hadjipavlou-Litina, D.; Lagunin, A.; Poroikov, B. V., Synthesis and anti-inflammatory activity of ethynylthiazoles. Khim. Geterotsiklicheskikh Soedin. 2006, 769-774.
Chemical PropertiesColourless Liquid
UsesAryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2
Uses2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity.
Uses2-Bromothiazole, is intended used for research purpose only. It is also used as Aryl halide which are used to N-arylate 5- and 7-azaindoles. Copper-catalyzed cyanation provides 2-cyanothiazole

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