2-ブロモ-3-メチルチオフェン

化学名:2-ブロモ-3-メチルチオフェン

英語名:2-Bromo-3-methylthiophene

CBNumberCB8147031

MFC5H5BrS

MW177.06

别名

2-ブロモ-3-メチルチオフェン

3-メチル-2-ブロモチオフェン

2-ブロモ-3-メチルチオフェン臭化物

2-ブロモ-3-メチルチオフェン物理性質

融点	<25 °C
沸点	173-176 °C (lit.)
比重(密度)	1.572 g/mL at 25 °C (lit.)
屈折率	n20/D 1.572(lit.)
闪点	155 °F
貯蔵温度	2-8°C
溶解性	soluble in Chloroform, Ethyl Acetate
水溶解度	Insoluble in water
外見	liquid
比重	1.580
色	Pale yellow
BRN	105719
CAS データベース	14282-76-9(CAS DataBase Reference)
NISTの化学物質情報	Thiophene, 2-bromo-3-methyl-(14282-76-9)

安全性情報

危険有害性情報のコード(GHS)

外観
無色～淡黄色、液体
用途
有機合成原料。
化学的特性
clear colorless to light yellow liquid
使用
2-Bromo-3-methylthiophene was used in the preparation of poly(3,3′′′-dimethyl-(2,2′:5′,2′:5′,2′′′)tetrathiophene)). It was also used in the preparation of 2-bromo-3-(bromomethyl)thiophene, lachrymatory compound.
主な応用
2-Bromo-3-methylthiophene is used as a pharmaceutical intermediate. It is used to prepare pyrazolo[3,4-d]pyrimidine derivatives as inhibitors of human enterovirus, coxsackievirus, echovirus, influenza virus, herpes simplex virus and rhinovirus. It is also used in the synthesis of oral α7 nicotinic receptor agonists.
製造方法
2-Bromo-3-methylthiophene synthesis: To a solution of glacial AcOH (100 mL), acetic anhydride (4.0 g, 0.039 mol), and 3-methylthiophene (9.82 g, 0.100 mol) as a stirred mixture was added NBS (19.6 g, 0.11 mol) in one portion with a slight exotherm to 44 oC. After 20 min the reaction mixture was poured onto ice, neutralized with sodium bisulfite and extracted with ether. The ether layer was washed with water and concentrated to give 11.3 g (64%) of 2-bromo-3-methylthiophene as a tan colored liquid in 88% purity by GC area % analysis: 1H NMR (CDCl3) d 7.1 (d, 1H, J=5.7 Hz), 6.7 (d, 1H, J=5.9 Hz), 2.2 (s, 3H).
一般的な説明
2-Bromo-3-methylthiophene is formed (approx. 90%) by bromination of 3-methyl thiophene with N-bromosuccinimide in the absence of benzoyl peroxide.