149846-93-5

Basic information

• Product Name: 1-phenyl-4,4,4-trifluorobut-2-yn-1-ol
• CAS NO: 149846-93-5
• Molecular Weight: 200.16
• Mol File: 149846-93-5.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 1-phenyl-4,4,4-trifluorobut-2-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-4,4,4-trifluorobut-2-yn-1-ol(149846-93-5)
• EPA Substance Registry System: 1-phenyl-4,4,4-trifluorobut-2-yn-1-ol(149846-93-5)

Safety Data

• Hazardous Substances Data: 149846-93-5(Hazardous Substances Data)

Upstream product

• 661-54-1 3,3,3-trifluoroprop-1-yne 
• 14856-86-1 (3,3,3-trifluoroprop-1-yn-1-yl)lithium 
• 100-52-7 benzaldehyde 
• 949112-27-0 (E)-2-chloro-4,4,4-trifluoro-1-phenylbut-2-en-1-ol 
• 754-12-1 2,3,3,3-tetrafluoro-propene 
• 102687-65-0 trans-1-chloro-3,3,3-trifluoropropene 
• 99728-16-2 (Z)-1-chloro-3,3,3-trifluoro-1-propene 
• 943610-08-0 1,1-dichloro-3,3,3-trifluoro-2-tosyloxypropene 
• 460-73-1 1,1,1,3,3-Pentafluoropropane 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 

Downstream Products

• 1037582-83-4 C₁₇H₁₄F₃N₃O 
• 1037582-99-2 C₁₇H₁₄F₃N₃O 
• 1037582-85-6 C₁₈H₂₄F₃N₃O 
• 1453495-96-9 (3S,4R)-3-methyl-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-97-0 (3S,4R)-3-(2-(benzyloxy)ethyl)-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 136964-14-2 (Z)-1-phenyl-4,4,4-trifluoro-2-buten-1-one 
• 3108-34-7 (E)-4,4,4-trifluoro-1-phenyl-2-buten-1-one 
• 1453495-81-2 (3S,4S)-3-butyl-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-88-9 (3S,4S)-3-methyl-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-89-0 (3S,4S)-3-isobutyl-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-91-4 (3S,4S)-3-(2-(benzyloxy)ethyl)-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-93-6 (3S,4R)-3-butyl-6-phenyl-4-(trifluoromethyl)-3,4-dihydro-2H-pyran-2-one 
• 1453495-98-1 (S)-methyl 2-((S)-1,1,1-trifluoro-4-oxo-4-phenylbutan-2-yl)hexanoate 
• 1453496-00-8 (S)-methyl 2-((R)-1,1,1-trifluoro-4-oxo-4-phenylbutan-2-yl)-hexanoate 

Relevant articles and documents

HFO-1234yf as a CF3-Building Block: Synthesis and Chemistry of CF3-Ynones

Reaction of low cost, readily available 4th generation refrigerant gas 2,3,3,3-tetrafluoropropene (HFO-1234yf) with lithium diisopropylamide (LDA) leads to formation of lithium 3,3,3-trifluoropropynide, addition of which to a range of aldehydes formed CF3-alkynyl alcohol derivatives on multigram scale, which were oxidised using Dess–Martin periodinane (DMP) to give substituted CF3-ynones with minimal purification required. Michael-type additions of alcohol and amine nucleophiles to CF3-ynones are rapid and selective, affording a range of CF3-enone ethers and enaminones in excellent yields with high stereoselectivity for the Z-isomer. By analogous reactions with difunctional nucleophiles, a wide range of CF3-substituted pharmaceutically relevant heterocyclic structures can be accessed, exemplified in the simple synthesis of the anti-arthritis drug celecoxib from HFO-1234yf in just three steps.

A Remarkable Influence of a Trifluoromethyl Group on the Reactions of β-Mercaptoalcohols with Fluorinated α-Bromoenones

Isomeric fluorinated α-bromoenones react with dinucleophilic β-mercaptoalcohols in CH2Cl2 at room temperature in the presence of Et3N in a multistep process. Depending on the position of the CF3 group, different O,S-heterocycles or non-cyclic products were obtained. With 3-bromo-1,1,1-trifluorobut-3-en-2-ones derivatives of 1,4-oxathianes were formed, but isomeric 2-bromo-4,4,4-trifluorobut-2-en-1-ones yielded 1,3-oxathiolanes or non-cyclic sulfides. The thia-Michael addition is proposed as the initial step of the reaction, and the final heterocyclization is governed by the location of the CF3 group.

Iron-Catalyzed Thiocyclization for the Synthesis of Trifluoro-methylated Benzothiophenes by C-H Functionalization of Aryl Disulfides

An iron-catalyzed thiocyclization of propynols with aryl disulfides has been developed for the synthesis of trifluoromethylated benzothiophenes. The one-pot tandem reaction involves Meyer-Schuster -rearrangement of propynols and radical cyclization through C-H functionalization of aryl disulfides. A variety of 2-trifluoroacyl benzothiophenes were prepared in moderate to good yields with good functional-group tolerance.