2-Bromothiazole

Base Information

• Chemical Name: 2-Bromothiazole
• CAS No.: 3034-53-5
• Molecular Formula: C3H2BrNS
• Molecular Weight: 164.026
• Hs Code.: 29341000
• European Community (EC) Number: 221-229-4
• NSC Number: 91532
• UNII: 53KY5HU6FR
• DSSTox Substance ID: DTXSID9062805
• Nikkaji Number: J101.493E
• Wikidata: Q72512865
• Mol file: 3034-53-5.mol

Synonyms:2-Bromothiazole;3034-53-5;2-Bromo-1,3-thiazole;Thiazole, 2-bromo-;2-bromo thiazole;2-bromo-thiazole;Thiazole, bromo-;C3H2BrNS;MFCD00005316;NSC 91532;53KY5HU6FR;EINECS 221-229-4;NSC-91532;2-Thiazolyl Bromide;bromothiazole;bromo-thiazole;2-bromothiazol;2- bromothiazole;NSC91532;2-Bromothiazole, 98%;UNII-53KY5HU6FR;SCHEMBL6063;C3-H2-Br-N-S;DTXSID9062805;BCP29431;STR03615;BBL027513;STK803405;AKOS000121266;AB00399;CS-W001223;PS-4269;AM803661;BP-20653;SY001649;B1280;BB 0263321;FT-0611616;EN300-21325;Q-100385;F2173-0032;2-Bromo-thiazole;2-bromo-1,3-thiazole

Chemical Property of 2-Bromothiazole

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 1.9mmHg at 25°C
• Melting Point: 171 °C
• Refractive Index: n20/D 1.593(lit.)
• Boiling Point: 170.999 °C at 760 mmHg
• PKA: 0.84±0.10(Predicted)
• Flash Point: 63.333 °C
• PSA: 41.13000
• Density: 1.857 g/cm³
• LogP: 1.90560
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane
• Water Solubility.: insoluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 162.90913
• Heavy Atom Count: 6
• Complexity: 50.1

Purity/Quality:

99% ^*data from raw suppliers

2-Bromothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC(=N1)Br
• 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
• Uses: Aryl halide used to N-arylate 5- and 7-azaindoles.1 Copper-catalyzed cyanation provides 2-cyanothiazole.2 2-Bromothiazole is a heterocyclic S compound to induce base-pair substitution and having mutagenic activity. 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

Technology Process of 2-Bromothiazole

There total 8 articles about 2-Bromothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

2-thiazolylamine (96-50-4) → 2-bromo-1,3-thiazole (3034-53-5,215777-74-5)

Guidance literature:

With copper(II) sulphate hydrate; phosphoric acid; nitric acid; sodium bromide; sodium nitrite; In water; at 0 - 7 ℃; for 6h;

DOI:10.1055/s-0031-1289710

Reference yield: 14.0%

1,3-thiazole (288-47-1) + 2,5-dibromothiophen (3141-27-3) → 2-bromo-1,3-thiazole (3034-53-5,215777-74-5)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;

DOI:10.1021/jacs.1c06481

Reference yield:

1,3-thiazole (288-47-1) → 2-bromo-1,3-thiazole (3034-53-5,215777-74-5)

Guidance literature:

With tetrachloromethane; N-Bromosuccinimide;

upstream raw materials:

1,3-thiazole

2-thiazolylamine

2,5-dibromothiophen

Downstream raw materials:

2-(methyl-thiazol-2-yl-amino)-ethanol

N-benzyl-N',N'-dimethyl-N-thiazol-2-yl-ethylenediamine

4-acetylamino-N-methyl-N-thiazol-2-yl-benzenesulfonamide

Zolamine

Refernces

• 1、 Uzelac, Eric J.,Rasmussen, Seth C.. "Synthesis of Brominated Thiazoles via Sequential Bromination-Debromination Methods". . p. 5947 - 5951. Retrieved 2017/06/07.
• 2、 -. "ALKYNE COMPOUNDS AS S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS". Page/Page column 142. . Retrieved 2016/05/02.