175655-85-3

Basic information

• Product Name: (R)-(+)-(1-trifluoromethyl)octanol
• CAS NO: 175655-85-3
• Molecular Weight: 198.229
• Mol File: 175655-85-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R)-(+)-(1-trifluoromethyl)octanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-(1-trifluoromethyl)octanol(175655-85-3)
• EPA Substance Registry System: (R)-(+)-(1-trifluoromethyl)octanol(175655-85-3)

Safety Data

• Hazardous Substances Data: 175655-85-3(Hazardous Substances Data)

Upstream product

• 26902-66-9 1,1,1-trifluorononan-2-one 

Downstream Products

• 128054-80-8 (S)-(-)-1-(trifluoromethyl)octyl p-hydroxybenzoate 
• 128054-77-3 (R)-(+)-1-(trifluoromethyl)octyl p-hydroxybenzoate 

Relevant articles and documents

Chiral Synthesis Via Organoboranes. 38 Selective Reductions. 48. Asymmetric Reduction of Trifluoromethyl Ketones by B-Chlorodiisopinocampheylborane in High Enantiomeric Purity

(-)-B-Chlorodiisopinocampheylborane TM,1>, introduced by us several years ago, has been shown to reduce prochiral aryl and alkyl perfluorinated ketones to the corresponding optically active alcohols in very high ee.For example, 2,2,2-trifluoroacetophenone, trifluoroacetyl-1-naphthalene, and trifluoroacetyl-2-naphthalene are all reduced with 1 within 1-3 d at rt in 90percent ee, 78percent ee and 91percent ee, respectively.The optical purity of 1-phenyl-2,2,2-trifluoroethanol is upgraded to = 99percent ee by crystallizing the initially formed products from pentane. 1,1,2,2,2- pentafluoropropiophenone and 1,1,2,2,3,3,3-heptafluorobutyrophenone are reduced in 3 d with 1 to the corresponding alcohols in 92percent ee and 87 percent ee, respectively.The reagent reduces alkyl trifluoromethyl ketones at a rate faster than that of the aryl derivatives, while still providing the product alcohols in very high ee.Thus, 1,1,1-trifluoroacetone, 1,1,1-trifluorononan-2-one, and 1,1,1-trifluorodecan-2-one are all reduced within 4 - 8 h in 89percent ee, 92percent ee, and 91percent ee, respectively.Even α-sec-alkyl trifluoromethyl ketones are handled by 1 very efficiently.Thus cyclohexyl trifluoromethyl ketone is reduced by 1 at rt in 12 h to the product alcohol in 87percent ee.In all of these cases the trifluoromethyl group acts as the enantiocontrolling larger group as compared to the aryl or alkyl group.This produces alcohol products with stereochemistry opposite to those obtained for the corresponding hydrogen analogs.The steric and electronic influence of the trifluoromethyl group in achieving enantiocontrol in assymmetric reductions is discussed.Keywords: asymmetric reduction; trifluoromethyl ketones; DIP-Chloride; high enantiomeric purity