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Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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(E)-1-[4-(Methylsulfanyl) phenyl]-3-phenylprop-2-en-1-one.
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.
J. Mol. Catal. A: Chem., 235(1), 98-107 (2005)
Liquid phase acetylation of thioanisole with acetic anhydride to 4-(methylthio) acetophenone (4-MTAP) using H-beta catalyst.
Catalysis Communications, 5(11), 659-663 (2004)
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