157925-24-1

Basic information

• Product Name: 4-Chloro-1-(3-Methyl-2-thienyl)-1-butanone
• Synonyms: 4-Chloro-1-(3-Methyl-2-thienyl)-1-butanone;4-CHLORO-1-(3-METHYLTHIOPHEN-2-YL)BUTAN-1-ONE
• CAS NO: 157925-24-1
• Molecular Formula: C9H11ClOS
• Molecular Weight: 202.70104
• Product Categories: Miscellaneous Reagents
• Mol File: 157925-24-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Chloro-1-(3-Methyl-2-thienyl)-1-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-1-(3-Methyl-2-thienyl)-1-butanone(157925-24-1)
• EPA Substance Registry System: 4-Chloro-1-(3-Methyl-2-thienyl)-1-butanone(157925-24-1)

Safety Data

• Hazardous Substances Data: 157925-24-1(Hazardous Substances Data)

Usage

Uses

4-Chloro-1-(3-methyl-2-thienyl)-1-butanone is used in the synthesis of intermediates of GABA uptake inhibitors.

Upstream product

• 14282-76-9 2-bromo-3-methylthiophene 
• 628-20-6 4-Chlorobutyronitrile 
• 95184-07-9 3-methyl-2-thienyl magnesium bromide 

Relevant articles and documents

The Synthesis of Novel GABA Uptake Inhibitors. Part 2. Synthesis of 5-Hydroxytiagabine, a Human Metabolite of the GABA Reuptake Inhibitor Tiagabine

(R)-1-(4-(2,5-Dihydro-3-methyl-5-oxothien-2-ylidene)-4-(3-methyl-2-thienyl)butyl)-3-piperidinecarboxylic acid (5-hydroxytiagabine) 13, has been prepared in 8 steps from 2-bromo-3-methylthiophene 3.Key steps are Grignard reactions, displacement of heteroaromatic chlorine with methoxy, and simultaneously demethylation and opening of a hydroxymethylcyclopropane with bromotrimethylsilane.An alternative approach involving acylation of 2-lithio-3-methylthiophene 17a was found less satisfying.A metalloporphyrin assisted hydroxylation of tiagabine 1 also yielded the target metabolite.The structure of 5-hydroxytiagabine was confirmed by NMR-data including COSY, ROESY, HMQC and HMBC experiments.