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533610

Sigma-Aldrich

2-Acetyl-5-methylthiophene

98%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C7H8OS
Numero CAS:
13679-74-8
Peso molecolare:
140.20
Numero CE:
237-181-2
Numero MDL:
MFCD00014529
Codice UNSPSC:
12352100
ID PubChem:
24877976
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Indice di rifrazione

n20/D 1.561 (lit.)

P. ebollizione

65-67 °C/1 mmHg (lit.)

Punto di fusione

24-28 °C (lit.)

Densità

1.106 g/mL at 25 °C (lit.)

Gruppo funzionale

ketone

Stringa SMILE

CC(=O)c1ccc(C)s1

InChI

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

Descrizione generale

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.

Applicazioni

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG0054
BCBV2604
BCBJ6419V
1442786V
1442786

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Palladium-catalysed direct 3-or 4-arylation of thiophene derivatives using aryl bromides.
Dong JJ, et al.
Tetrahedron, 50(23), 2778-2781 (2009)
Zinc azaphthalocyanines with thiophen-2-yl, 5-methylthiophen-2-yl and pyridin-3-yl peripheral substituents: Additive substituent contributions to singlet oxygen production.
M?rkved EH, et al.
Dyes and Pigments, 82(3), 276-285 (2009)
Novel Dithienylethenes with Extended ??Systems: Synthesis by Aldol Condensation and Photochromic Properties.
Altenhoner K, et al.
European Journal of Organic Chemistry, 2010(31), 6033-6037 (2010)
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)
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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