111423-27-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
(S)-(-)-1,1,1-Trifluorodecan-2-ol is utilized as a chiral building block in the synthesis of various pharmaceutical and agrochemical products. Its unique stereochemistry allows for the creation of enantiomerically pure compounds, which is essential for the development of effective and safe drugs and agrochemicals.
Used in Organic Chemistry:
In the field of organic chemistry, (S)-(-)-1,1,1-Trifluorodecan-2-ol serves as a valuable chiral building block, enabling the synthesis of complex organic molecules with specific stereochemistry. This is particularly important in the development of new compounds with targeted biological activities.
Used in Material Science:
(S)-(-)-1,1,1-Trifluorodecan-2-ol has been studied for its potential application in the development of new materials. Its hydrophobic and lipophilic properties make it a promising candidate for use in the creation of materials with specific properties, such as improved solubility or stability.
Used as a Reagent in Organic Synthesis:
In addition to its role as a building block, (S)-(-)-1,1,1-Trifluorodecan-2-ol is also used as a reagent in organic synthesis. Its unique properties allow it to participate in various chemical reactions, facilitating the synthesis of a wide range of organic compounds.
Used in Industrial Applications:
The strong hydrophobic and lipophilic properties of (S)-(-)-1,1,1-Trifluorodecan-2-ol make it useful in certain industrial applications, such as in the formulation of products that require specific solubility or compatibility with other components. Its unique characteristics can enhance the performance of these products in their intended applications.

InChI:InChI=1/C10H19F3O/c1-2-3-4-5-6-7-8-9(14)10(11,12)13/h9,14H,2-8H2,1H3

Upstream product

• 26902-68-1 1,1,1-trifluorodecan-2-one 
• 75-18-3 dimethylsulfide 
• 3761-92-0 n-hexylmagnesium bromide 
• 130025-34-2 (S)-2-trifluoromethyl-oxirane 
• 108535-32-6 Toluene-4-sulfonic acid (R)-4,4,4-trifluoro-3-(tetrahydro-pyran-2-yloxy)-butyl ester 
• 26902-81-8 (+)-1,1,1-trifluoro-2-decanol 
• 629-05-0 n-octyne 
• 123-29-5 ethyl pelargonate 
• 85336-10-3 1,1,1-trifluoro-3-decyn-2-one 
• 122920-69-8 (Z)-hexyl-3-hydroxy-4,4,4-trifluoro-1-butene 
• 128726-31-8 1-hexyl-3-hydroxy-4,4,4-trifluoro-1-butyne 
• 175776-99-5 (S)-1,1,1-trifluorodecan-2-yl acetate 
• 128779-62-4 Acetic acid (Z)-1-trifluoromethyl-non-2-enyl ester 
• 111423-32-6 (E)-1-hexyl-3-hydroxy-4,4,4-trifluoro-1-butene 

Downstream Products

• 128054-85-3 (S)-(-)-1-(trifluoromethyl)nonyl p-hydroxybenzoate 
• 124689-86-7 (R)-(+)-1-(trifluoromethyl)nonyl p-hydroxybenzoate 
• 135252-68-5 (S)-(-)-4-<(1-trifluoromethylnonyloxycarbonyl)phenyl> 4'-octyloxybiphenyl-4-carboxylate 

Relevant academic research and scientific papers

Different stereochemistry for the reduction of trifluoromethyl ketones and methyl ketones catalyzed by alcohol dehydrogenase from Geotrichum

Reduction of trifluoromethyl ketones by a crude alcohol dehydrogenase from Geotrichum affords (S)-trifluoromethyl carbinols in excellent ee, whereas the reduction of methyl ketones gives the corresponding alcohols of the opposite configuration in excellent ee.

Enantioselective Rhodium(I)-Catalyzed Hydrogenation of Trifluoromethyl Ketones

(Matrix Presented) The asymmetric hydrogenation of trifluoromethyl ketones to yield chiral α-trifluoromethyl alcohols with enantiomeric excesses up to 98% was achieved in the presence of chiral rhodium-(amidephosphine-phosphinite) complexes.

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.

Highly enantioselective synthesis of long chain alkyl trifluoromethyl carbinols and β-thiotrifluoromethyl carbinols through lipases

Among a variety of lipases tested, Candida antarctica lipase has been found to promote the enantioselective acylation of long chain alkyl trifluoromethyl carbinols 1a-4a and β-thiotrifluoromethyl carbinols 5a-7a, producing both R and S enantiomeric alcohols in good to excellent chemical yield and enantioselectivity. In all cases the lipase preferentially acylates the S enantiomer, irrespective the presence or not of a sulfur atom in β position to the hydroxyl group. When the reaction was carried out on the non-fluorinated substrates 1c-2c, the process occurred much faster and with higher e.e. of the less reacting enantiomer than when conducted on the fluorinated substrates.

Efficient synthesis of optically pure 1,1,1-trifluoro-2-alkanols through lipase-catalyzed acylation in organic media

Lipase-catalyzed esterification was successfully utilized for the optical resolution of 1,1,1-trifluoro-2-alkanol 1 when racemic 1 was treated with lipase from Candida antarctica in hexane in the presence of molecular sieves (4 A) to provide the corresponding (S)-acetate 2 in an optically pure state. Alkanol 1 is known as an important component of liquid crystal compounds which display remarkable ferroelectric liquid crystal (FLC) characteristics. Five types of optically pure alkanols, i.e., 1,1,1-trifluoro-2-octanol (1a), 1,1,1-trifluoro-2-nonanol (1b), 1,1,1-trifluoro-2-decanol (1c), 1,1,1-trifluoro-2-undecanol (1d), and 1,1,1-trifluoro-8-(benzyloxy)-2-octanol (1e), were thus obtained by the lipase-catalyzed acylation.

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

Stereoselective Synthesis of Fluorinated Materials Catalyzed by an Antibody

A monoclonal antibody, elicited by a transition-state analogue for the hydrolysis of fluorinated esters, acted as an enzymelike catalyst for the preparation of chiral fluorinated compounds. The syntheses of (R)- or (S)-1-(fluoroalkyl)alkanols and an allyl

TRIFLUOROPROPENE OXIDE AS A TRIFLUOROMETHYL SOURCE. PREPARATION OF OPTICALLY ACTIVE ALCOHOLS

Optically active 3,3,3-trifluoropropene oxide (TFPO) was converted to 1,1,1-trifluoro-2-ols via Grignard type or Friedel-Crafts type reaction.The regio-selectivity of the latter reaction was discussed through an MO calculation.

SYNTHETIC APPROACH TO STEREOISOMERS OF ALLYLIC ALCOHOLS POSSESING A TRIFLUOROMETHYL GROUP

A number of stereoisomers of optically pure allylic alcohols with a trifluoromethyl group were prepared, utilizing the enantiotopic specifity of assymetric hydrolysis of their acetates by hydrolyses.Their absolute configurat