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Merck
CN

533610

Sigma-Aldrich

2-乙酰基-5-甲基噻吩

98%

别名:

1-(5-Methyl-2-thienyl)ethanone, 1-(5-Methylthiophen-2-yl)ethan-1-one, 1-(5-Methylthiophen-2-yl)ethanone, 2-Methyl-5-acetylthiophene, 5-Methyl-2-thienyl methyl ketone, Methyl 5-methyl-2-thienyl ketone

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关于此项目

经验公式(希尔记法):
C7H8OS
化学文摘社编号:
分子量:
140.20
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
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质量水平

方案

98%

折射率

n20/D 1.561 (lit.)

沸点

65-67 °C/1 mmHg (lit.)

mp

24-28 °C (lit.)

密度

1.106 g/mL at 25 °C (lit.)

官能团

ketone

SMILES字符串

CC(=O)c1ccc(C)s1

InChI

1S/C7H8OS/c1-5-3-4-7(9-5)6(2)8/h3-4H,1-2H3

InChI key

YOSDTJYMDAEEAZ-UHFFFAOYSA-N

一般描述

2-Acetyl-5-methylthiophene is a volatile organic compound formed during the reaction between L-cysteine and dihydroxyacetone in glycerine or triglyceride solvent system. It can be prepared by reacting 2-methylthiophene with acetic anhydride. 2-Acetyl-5-methylthiophene undergoes palladium-catalyzed cross-coupling reaction with aryl bromides to form C-4 arylated product. It reacts with 1,2-bis(5-formyl-2-methylthiophen-3-yl)cyclopentene via Aldol condensation to form a chalcone with photochromic property. The standard molar enthalpies of combustion, formation and vaporization of 2-acetyl-5-methylthiophene are 4341.9 ± 1.8kJ/mol, 158.0 ± 2.1kJ/mol and 62.0 ± 2.6kJ/mol, respectively.

应用

2-Acetyl-5-methylthiophene may be used in the preparation of:
  • 2-ethyl-5-methylthiophene
  • (5-methylthiophen-2-yl)glyoxal
  • (2E)-1-(5-methylthiophen-2-yl)-3-(pyridin-3-yl)prop-2-en-1-one
  • ethyl 3-(5-methylthiophen-2-yl)-3-oxopropanoate

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

法规信息

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分析证书(COA)

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Experimental thermochemical study of the three methyl substituted 2-acetylthiophene isomers.
da Silva MAVR and Santos AFLOM.
The Journal of Chemical Thermodynamics, 40(8), 1309-1313 (2008)
Straightforward access to diketopyrrolopyrrole (DPP) dimers.
Stas S, et al.
Dyes and Pigments, 97(1), 198-208 (2013)
Acylation studies in the thiophene and furan series. IV. Strong inorganic oxyacids as catalysts.
Hartough HD and Kosak AI.
Journal of the American Chemical Society, 69(12), 3093-3096 (1947)
Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized 2?, 3??-Thiazachalcones.
Ustaa A, et al.
Helvetica Chimica Acta, 90, 1482-1482 (2007)
Efficient guaiazulene and chamazulene syntheses involving [6+4] cycloadditions.
Mukherjee D, et al.
Journal of the American Chemical Society, 1010(1), 251-252 (1979)

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