533610
2-Acetyl-5-methylthiophene
98%
Synonym(s):
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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About This Item
Empirical Formula (Hill Notation):
C7H8OS
CAS Number:
Molecular Weight:
140.20
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
237-181-2
MDL number:
Assay:
98%
Quality Level
assay
98%
refractive index
n20/D 1.561 (lit.)
bp
65-67 °C/1 mmHg (lit.)
mp
24-28 °C (lit.)
density
1.106 g/mL at 25 °C (lit.)
functional group
ketone
SMILES string
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
General description
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.
Application
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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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)
Straightforward access to diketopyrrolopyrrole (DPP) dimers.
Stas S, et al.
Dyes and Pigments, 97(1), 198-208 (2013)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 533610-25G | 04061833045862 |