30933-31-4

Basic information

• Product Name: Ethanone, 2,2,2-trifluoro-1-(3-thienyl)- (9CI)
• Synonyms: Ethanone, 2,2,2-trifluoro-1-(3-thienyl)- (9CI);2,2,2-trifluoro-1-(thiophen-3-yl)ethan-1-one
• CAS NO: 30933-31-4
• Molecular Formula: C₆H₃F₃OS
• Molecular Weight: 180.1476296
• Product Categories: ACETYLHALIDE
• Mol File: 30933-31-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 169.7°C at 760 mmHg
• Flash Point: 56.4°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 1.52mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: Ethanone, 2,2,2-trifluoro-1-(3-thienyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2,2,2-trifluoro-1-(3-thienyl)- (9CI)(30933-31-4)
• EPA Substance Registry System: Ethanone, 2,2,2-trifluoro-1-(3-thienyl)- (9CI)(30933-31-4)

Safety Data

• Hazardous Substances Data: 30933-31-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H3F3OS/c7-6(8,9)5(10)4-1-2-11-3-4/h1-3H

Upstream product

• 872-31-1 3-Bromothiophene 
• 1547-87-1 N,N-dimethyl-2,2,2-trifluoroacetamide 
• 407-25-0 trifluoroacetic anhydride 
• 383-63-1 ethyl trifluoroacetate, 

Relevant articles and documents

Two Classes of Enzymes of Opposite Stereochemistry in an Organism: One for Fluorinated and Another for Nonfluorinated Substrates

Reduction of methyl ketones by dried cells of Geotrichum candidum (APG4) afforded (S)-alcohols in excellent enantiomeric excess (ee), whereas the reduction of trifluoromethyl ketones gave the corresponding alcohols of the opposite configuration also in excellent ee. The replacement of the methyl moiety with a trifluoromethyl group alters both the bulkiness and the electronic properties, the effect of which on the stereoselectivity was examined. No inversion in stereochemistry was observed in the reduction of hindered ketones such as isopropyl ketone, while the stereoselectivity was inverted in the reduction of ketones with electron-withdrawing atoms such as chlorine. The mechanism for the inversion in stereochemistry was investigated by enzymatic studies. Several enzymes with different stereoselectivities were isolated; one of them catalyzed the reduction of methyl ketones, and another with the opposite stereoselectivity catalyzed the reduction of trifluoromethyl ketones. Furthermore, both APG4 and the isolated enzyme were applied to the reduction of fluorinated ketones on a preparative scale, which resulted in the synthesis of chiral fluorinated alcohols with excellent ee.

A Convenient Preparation of Aryltrifluoromethylketones

The reaction of aryllithium reagents prepared by halogen metal exchange or direct metallation with α,α,α-trifluoro-N,N-dimethylacetamide give the corresponding aryltrifluoromethylketones in good yield.