3034-53-5

Basic information

• Product Name: 2-Bromothiazole
• Synonyms: 2-THIAZOLYL BROMIDE;2-BROMOTHIOAZOLE;2-BROMOTHIAZOLE;2-BROMO-1,3-THIAZOLE;TIMTEC-BB SBB003918;2-bromo-thiazol;2-Bromothiazole, 98+%;Thiazole, 2-bromo-
• CAS NO: 3034-53-5
• Molecular Formula: C₃H₂BrNS
• Molecular Weight: 164.02
• EINECS: 221-229-4
• Product Categories: ThiazolesHeterocyclic Building Blocks;Halides;Heterocycles;Thiazoles, Isothiazoles &Benzothiazoles;API intermediates;Organohalides;Thiazole;Heterocyclic Compounds;Thiazoles;Sulfur & Selenium Compounds;Thiazoles, Isothiazoles & Benzothiazoles;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;C3 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl bromide
• Mol File: 3034-53-5.mol

Chemical Properties

• Melting Point: 171 C
• Boiling Point: 171 °C(lit.)
• Flash Point: 146 °F
• Appearance: Clear colorless to orange-brown/Liquid
• Density: 1.82 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.9mmHg at 25°C
• Refractive Index: n20/D 1.593(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane
• PKA: 0.84±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 105724
• CAS DataBase Reference: 2-Bromothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromothiazole(3034-53-5)
• EPA Substance Registry System: 2-Bromothiazole(3034-53-5)

Safety Data

• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• RIDADR: 1993
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT, FLAMMABLE
• Hazardous Substances Data: 3034-53-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Bromothiazole is used as an aryl halide for N-arylation of 5and 7-azaindoles, which are important in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
2-Bromothiazole is used as a raw material to produce 2-acetylthiazole, antibiotics, and anticholinergic drugs, contributing to the development of medications for various health conditions.
Used in Research:
2-Bromothiazole is intended for research purposes only, where it can be used to study its mutagenic activity and potential applications in the development of new pharmaceuticals.
Used in Synthesis of Camalexin:
2-Bromothiazole is used as a raw material to produce camalexin through a reaction with indolylmagnesium iodide, which is a phytoalexin involved in plant defense mechanisms.
Used in Thiazole Reagents:
2-Bromothiazole is used to prepare thiazole Grignard reagents and thiazolyllithium compounds, which can be converted into thiazole-2-carboxylic acid via a halogen-metal exchange reaction, further expanding its applications in organic synthesis.
Used in Inhibitors of Cyclin-Dependent Kinases:
2-Bromothiazole has been used to synthesize N-aryl aminothiazoles, which function as inhibitors of cyclin-dependent kinases, playing a role in the development of potential cancer treatments.
Used in Anti-Inflammatory Agents:
2-Bromothiazole may be involved in the synthesis of ethynylthiazoles, which exhibit anti-inflammatory activity, contributing to the development of new treatments for inflammation-related conditions.
Used in Copper-Catalyzed Cyanation:
2-Bromothiazole is used in copper-catalyzed cyanation reactions to provide 2-cyanothiazole, which can be further utilized in the synthesis of various organic compounds.

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.

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

Upstream product

• 288-47-1 1,3-thiazole 
• 96-50-4 2-thiazolylamine 
• 3141-27-3 2,5-dibromothiophen 

Downstream Products

• 122320-81-4 2-(methyl-thiazol-2-yl-amino)-ethanol 
• 101117-32-2 N-benzyl-N',N'-dimethyl-N-thiazol-2-yl-ethylenediamine 
• 66507-95-7 4-acetylamino-N-methyl-N-thiazol-2-yl-benzenesulfonamide 
• 553-13-9 Zolamine 
• 100585-58-8 N-(4-chlorophenyl)thiazol-2-amine 
• 72-14-0 Sulfathiazole 
• 127-76-4 4'-(thiazol-2-ylsulfamoyl)acetanilide 
• 14542-13-3 2-methoxythiazole 
• 14190-59-1 1,3-thiazole-2-carboxylic acid 
• 41731-70-8 2-bromo-thiazole-5-sulfonic acid 
• 4175-70-6 2-(piperidin-1-yl)thiazole 
• 21429-06-1 2-(morpholine-1-yl)thiazole 
• 69390-09-6 bis(1,3-thiazol-2-yl) sulfide 
• 90418-58-9 --keton 

Relevant articles and documents

Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer

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.

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.

Synthetic method for 2-acetyl thiazole

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.

ALKYNE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS

Provided are compounds of formula (Ia) and pharmaceutically acceptable salts thereof, wherein A, B, R 1, R 2, m and n are as defined herein, which are active as inhibitors of S-Nitrosoglutathione reductase (GSNOR). These compounds prevent, inhibit, or suppress the action of GSNOR and are therefore useful in the treatment of GSNOR mediated diseases, disorders, syndromes or conditions such as, e.g., pulmonary hypertension, acute respiratory distress syndrome (ARDS), asthma, bronchospasm, cough, pneumonia, pulmonary fibrosis, interstitial lung diseases, cystic fibrosis and chronic obstructive pulmonary disease (COPD).

Convenient preparation of halo-1,3-thiazoles: Important building blocks for materials and pharmaceutical synthesis

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.

CARBOXYLIC ACID DERIVATIVES AND DRUGS CONTAINING THE SAME

The present invention provides a novel carboxylic acid compound, a salt thereof or a hydrate of them useful as an insulin-resistant improver, and a medicament comprising the compound as an active ingredient. That is, the present invention provides a carboxylic acid compound represented by the following formula (I), a salt thereof, an ester thereof or a hydrate of them. In the formula, R1 represents hydrogen atom, hydroxyl group or a C1-6 alkyl group etc. which may have one or more substituents; L represents a single or double bond or a C1-6 alkylene group etc. which may have one or more substituents; M represents a single bond or a C1-6 alkylene group etc. which may have one or more substituents; T represents a single bond or a C1-3 alkylene group which may have one or more substituents; W represents carboxyl group or a group represented by the formula -CON(Rw1)Rw2 (wherein Rw1 and Rw2 are the same as or different from each other and each represents hydrogen atom, formyl group etc.) etc.; represents a single or double bond; X represents oxygen atom or a C2-6 alkenylene group etc. which may have one or more substituents; Y represents a C5-12 aromatic hydrocarbon group etc. which may have one or more substituents and which may have one or more heteroatoms; and ring Z represents a C5-6 aromatic hydrocarbon group which may have 0 to 4 substituents and which may have one or more heteroatoms.

Tetrahalogenomethanes: Simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds

Tetrabromo- or tetrachloromethane and 2-lithio derivatives of aromatic heterocycles rapidly produce the corresponding 2-bromo or 2-chloro derivatives in high yields through a metal-halogen exchange mechanism. This kind of reaction was also used to obtain, in good yields, 5-bromo-2-chlorothiazole and 5-bromo-2-chloro-N-methylimidazole.

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.