- 2-Bromothiazole
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- $0.00 / 25KG
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2025-12-01
- CAS:3034-53-5
- Min. Order: 1KG
- Purity: 99.0%
- Supply Ability: 10000KGS
- 2-Bromothiazole
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- $32.00 / 1kg
-
2025-09-25
- CAS:3034-53-5
- Min. Order: 1kg
- Purity: 99%
- Supply Ability: g-kg-tons, free sample is available
- 2-Bromothiazole
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- $0.00 / 1KG
-
2025-04-04
- CAS:3034-53-5
- Min. Order: 1KG
- Purity: 98%
- Supply Ability: 1ton
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| | 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 | | form | Liquid | | pka | 0.84±0.10(Predicted) | | color | Clear colorless to orange-brown | | Specific Gravity | 1.836 | | Water Solubility | insoluble | | BRN | 105724 | | InChI | 1S/C3H2BrNS/c4-3-5-1-2-6-3/h1-2H | | InChIKey | RXNZFHIEDZEUQM-UHFFFAOYSA-N | | SMILES | Brc1nccs1 | | CAS DataBase Reference | 3034-53-5(CAS DataBase Reference) | | NIST Chemistry Reference | Thiazole, 2-bromo-(3034-53-5) | | EPA Substance Registry System | Thiazole, 2-bromo- (3034-53-5) |
| Hazard Codes | Xi,F | | Risk Statements | 36/37/38 | | Safety Statements | 23-24/25-36-26 | | RIDADR | 1993 | | WGK Germany | 3 | | TSCA | TSCA listed | | HazardClass | IRRITANT, FLAMMABLE | | HS Code | 29341000 | | Storage Class | 12 - Non Combustible Liquids |
| | 2-Bromothiazole Usage And Synthesis |
| Description | It 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 |
- Ayer, W. A.; Craw, P. A.; Ma, Y. T.; Miao, S. C., SYNTHESIS OF CAMALEXIN AND RELATED PHYTOALEXINS. Tetrahedron 1992, 48, 2919-2924.
- Kurkjy, R. P.; Brown, E. V., THE PREPARATION OF THIAZOLE GRIGNARD REAGENTS AND THIAZOLYLLITHIUM COMPOUNDS. J. Am. Chem. Soc. 1952, 74, 6260-6262.
- 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.
- 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.
- 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 Properties | Colourless Liquid | | Uses | Aryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2 | | Uses | 2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity. | | Uses | 2-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 | | Synthesis | General procedure for the synthesis of 2-bromothiazole from 2-aminothiazole: 2-aminothiazole (0.25 mol) and 150 mL of 45% sulfuric acid were added to a 500 mL reaction flask, and stirred until the 2-aminothiazole was completely dissolved. The reaction mixture was cooled to 2 °C and 50 mL of 65% concentrated nitric acid was added slowly and dropwise, controlling the reaction temperature to not exceed 10 °C. Subsequently, 50 mL of 5 mol/L sodium nitrite solution was added slowly dropwise, and after the dropwise addition was completed, stirring was continued for 1 hour to keep the reaction temperature below 7 °C. The reaction mixture was dripped into a 200 mL solution containing 74 g of sodium bromide and 40 g of copper sulfate through a dropping funnel for the bromination reaction, controlling the temperature at 6 °C, and the dropping time was about 1.5 hours. After the reaction was completed, N2 gas was removed. After cooling, the pH of the reaction mixture was adjusted to 6-7 with 20% NaOH solution, followed by hydrodistillation to collect the aqueous solution containing 2-bromothiazole. After drying with magnesium sulfate, vacuum distillation was carried out to collect the fraction with a boiling point of 71~73 °C/2.4 kPa to give 35.2 g of 2-bromothiazole in 85.8% yield. In this reaction, keeping the reaction temperature in the range of 0~10 °C not only accelerated the reaction rate, but also reduced the occurrence of side reactions, thus significantly increasing the reaction yield. | | References | [1] Synthesis, 2012, vol. 44, # 7, p. 1026 - 1029
[2] Patent: CN105348216, 2016, A. Location in patent: Paragraph 0048; 0049
[3] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 77,78
[4] Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 554 - 564
[5] Patent: WO2016/55947, 2016, A1. Location in patent: Page/Page column 142 |
| | 2-Bromothiazole Preparation Products And Raw materials |
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