3034-53-5 Usage
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
Different sources of media describe the Uses of 3034-53-5 differently. You can refer to the following data:
1. Aryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2
2. 2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity.
3. 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
Check Digit Verification of cas no
The CAS Registry Mumber 3034-53-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,3 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3034-53:
(6*3)+(5*0)+(4*3)+(3*4)+(2*5)+(1*3)=55
55 % 10 = 5
So 3034-53-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H2BrNS/c4-3-5-1-2-6-3/h1-2H
3034-53-5Relevant articles and documents
Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer
Bandar, Jeffrey S.,Klaus, Danielle R.,Puleo, Thomas R.
supporting information, p. 12480 - 12486 (2021/08/24)
We report a general protocol for the direct C-H etherification of N-heteroarenes. Potassium tert-butoxide catalyzes halogen transfer from 2-halothiophenes to N-heteroarenes to form N-heteroaryl halide intermediates that undergo tandem base-promoted alcohol substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcohols with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions.
Synthetic method for 2-acetyl thiazole
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Paragraph 0048; 0049, (2016/10/08)
The invention relates to a synthetic method for 2-acetyl thiazole. The synthetic method comprises the following steps: firstly, preparation of 2-amino thiazole is carried out, namely, toluene, thiourea and chloroacetaldehyde are mixed, a reaction is carried out with stirring at a constant temperature, and 2-amino thiazole is prepared; secondly, preparation of 2-bromo thiazole is carried out, namely, 2-amino thiazole is dissolved in sulfuric acid, cooling is carried out, a sodium nitrite aqueous solution is added drop by drop slowly at a controlled temperature after concentrated nitric acid is added drop by drop, stirring is carried out continuously, a reaction is carried out, the solution after the reaction is added in a mixed solution of sodium bromide and copper sulphate, a bromination reaction is carried out, and 2-bromo thiazole is prepared; thirdly, preparation of 2-acetyl thiazole is carried out, namely, 2-bromo thiazole is added in a butyllithium solution, stirring is carried out, then ethyl acetate is added, a reaction is carried out, and 2-acetyl thiazole is prepared. The acetylation step of 2-bromo thiazole is improved, the reaction raw material ratio and the reaction temperature are optimized, the high yield of the reaction is achieved, safe and reliable operation of the experiment is ensured effectively, and unexpected technical effects are achieved.
Convenient preparation of halo-1,3-thiazoles: Important building blocks for materials and pharmaceutical synthesis
Grubb, Alan M.,Schmidt, Michael J.,Seed, Alexander J.,Sampson, Paul
experimental part, p. 1026 - 1029 (2012/05/05)
Convenient, scalable and high-yielding approaches to 2,5- and 2,4-dibromo-1,3-thiazole are reported that offer significant improvements over previously reported approaches. 2,5-Dibromo-1,3-thiazole was generated in two steps from commercially inexpensive 2-amino-1,3-thiazole, whereas 2,4-dibromo-1,3-thiazole was generated in a single step from commercially inexpensive 1,3-thiazolidine-2,4-dione. As part of this study, convenient approaches to 2-bromo- and 2-iodo-1,3-thiazole were also developed. Georg Thieme Verlag Stuttgart · New York.
