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396583

Sigma-Aldrich

4′-(Methylthio)acetophenone

97%

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About This Item

Linear Formula:
CH3SC6H4COCH3
CAS Number:
Molecular Weight:
166.24
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

97%

mp

80-82 °C (lit.)

SMILES string

CSc1ccc(cc1)C(C)=O

InChI

1S/C9H10OS/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3

InChI key

JECUZQLBQKNEMW-UHFFFAOYSA-N

General description

4′-(Methylthio)acetophenone (4-(Methylthio)acetophenone, p-(methylthio) acetophenone, 4-MTAP) is a sulphur containing organic building block. It is a key intermediate in drug synthesis. Its industrial preparation, via Friedel-Crafts acylation reaction in the presence of aluminium chloride as catalyst and acetyl chloride as acylating agent has been reported. It has been prepared by the acetylation reaction of thioanisole with acetic anhydride in the presence of solid acid catalyst.

Application

4′-(Methylthio)acetophenone may be used for the synthesis of Vioxx (Rofecoxib), an non-steroidal anti-inflammatory drug (NSAID). It may be used in the synthesis of (E)-1-[4-(methylsulfanyl)phenyl]-3-phenylprop-2-en-1-one.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Liquid phase acetylation of thioanisole with acetic anhydride to 4-(methylthio) acetophenone (4-MTAP) using H-beta catalyst.
Sawant DP and Halligudi SB.
Catalysis Communications, 5(11), 659-663 (2004)
(E)-1-[4-(Methylsulfanyl) phenyl]-3-phenylprop-2-en-1-one.
Thiruvalluvar A, et al.
Acta Crystallographica Section E, Structure Reports Online, 64(7), o1263-o1263 (3008)
Experimental and theoretical analysis of Friedel-Crafts acylation of thioanisole to 4-(methylthio) acetophenone using solid acids.
Yadav GD and Bhagat RD.
J. Mol. Catal. A: Chem., 235(1), 98-107 (2005)

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