147991-84-2

Basic information

• Product Name: (S)-(-)-1,1,1-TRIFLUORONONAN-2-OL
• Synonyms: (S)-(-)-1,1,1-TRIFLUORONONAN-2-OL;(S)-(-)-1,1,1-Trifluorononan-2-ol (>98%ee);(2S)-(-)-1,1,1-Trifluorononan-2-ol;(2S)-(-)-2-Hydroxy-1,1,1-trifluorononane
• CAS NO: 147991-84-2
• Molecular Formula: C₉H₁₇F₃O
• Molecular Weight: 198.23
• Mol File: 147991-84-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 67-68/6mm
• Flash Point: 96.3°C
• Appearance: /
• Density: 1.035g/cm³
• Vapor Pressure: 0.0363mmHg at 25°C
• Refractive Index: 1.393
• CAS DataBase Reference: (S)-(-)-1,1,1-TRIFLUORONONAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1,1,1-TRIFLUORONONAN-2-OL(147991-84-2)
• EPA Substance Registry System: (S)-(-)-1,1,1-TRIFLUORONONAN-2-OL(147991-84-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 147991-84-2(Hazardous Substances Data)

Usage

General Description

(S)-(-)-1,1,1-Trifluorononan-2-ol is a type of chemical compound that belongs to the organic chemical class known as Alcohols, specifically Nonanol. It is characterized by a hydroxy functional group attached to the carbon atom of a nonane backbone. The descriptive (S)-(-) indicates the compound's chiral configuration or the arrangement of atoms in the molecule. The trifluoro component suggests the presence of three fluoride atoms. While it is not a common substance in household products or commercial applications, it is often used in scientific research, particularly within chemistry, for various studies or as a chemical building block. Details regarding its physical and chemical properties, toxicity, or potential uses are generally available from specialized scientific databases or chemical suppliers.

InChI:InChI=1/C9H17F3O/c1-2-3-4-5-6-7-8(13)9(10,11)12/h8,13H,2-7H2,1H3/t8-/m0/s1

Upstream product

• 26902-66-9 1,1,1-trifluorononan-2-one 
• 106-32-1 octanoic acid ethyl ester 

Downstream Products

• 128054-80-8 (S)-(-)-1-(trifluoromethyl)octyl p-hydroxybenzoate 

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.

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