110270-42-3

Basic information

• Product Name: (R)-(+)-1-FLUORO-2-OCTANOL
• Synonyms: (R)-(+)-1-FLUORO-2-OCTANOL;((+)-1-Fluoro-2-octanol
• CAS NO: 110270-42-3
• Molecular Formula: C₈H₁₇FO
• Molecular Weight: 148.22
• Mol File: 110270-42-3.mol

Chemical Properties

• Boiling Point: 96-97 °C22 mm Hg(lit.)
• Flash Point: 167 °F
• Appearance: /
• Density: 1.254 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.069mmHg at 25°C
• Refractive Index: 1.412
• PKA: 14.12±0.20(Predicted)
• CAS DataBase Reference: (R)-(+)-1-FLUORO-2-OCTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-FLUORO-2-OCTANOL(110270-42-3)
• EPA Substance Registry System: (R)-(+)-1-FLUORO-2-OCTANOL(110270-42-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 110270-42-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-(+)-1-FLUORO-2-OCTANOL is used as a building block in the synthesis of pharmaceutical and agrochemical products, contributing to the development of new compounds with specific therapeutic and agricultural benefits.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, (R)-(+)-1-FLUORO-2-OCTANOL serves as a chiral auxiliary, playing a crucial role in controlling the stereochemistry of chemical reactions. This application is vital for the production of enantiomerically pure compounds, which are essential in various industries, including pharmaceuticals where the stereochemistry of a molecule can significantly affect its biological activity.
Used in Flavor and Fragrance Production:
(R)-(+)-1-FLUORO-2-OCTANOL also finds potential applications in the creation of flavors and fragrances, capitalizing on its sweet odor to enhance or create novel scents for the perfumery, food, and beverage industries.
Used in the Development of Chiral Building Blocks:
Its ability to act as a chiral building block makes (R)-(+)-1-fluoro-2-octanol a valuable component in the development of new compounds with specific stereochemical properties, which are important in various chemical and biological processes.

InChI:InChI=1/C8H17FO/c1-2-3-4-5-6-8(10)7-9/h8,10H,2-7H2,1H3/t8-/m1/s1

Upstream product

• 77495-66-0 (R)-1,2-epoxyoctane 
• 590-05-6 1-fluoro-2-octanone 
• 3761-92-0 n-hexylmagnesium bromide 
• 115899-99-5 1-fluoro-2-octyl acetate 

Downstream Products

• 141671-01-4 2-[4-(1-monofluoromethylheptyloxymethyl)phenyl]-5-decylpyrimidine 

Relevant articles and documents

SYNTHESIS OF OPTICALLY ACTIVE FLUORINATED MATERIALS BY USE OF IMMOBILIZED ENZYMES FOR ASYMMETRIC HYDROLYSIS

A synthetic approach to optically active fluorinated compounds was based on the enantiotopic specificity of asymmetric hydrolysis by an immobilized enzyme.

Selective Reductions. 53. Asymmetric Reduction of α-Fluoromethyl Ketones with B-Chlorodiisopinocampheylborane or B-Isopinocampheyl-9-borabicyclononane. Combined Electronic and Steric Contributions to the Enantiocontrol Process

A systematic study of the asymmetric reduction of aryl and alkyl α-fluoroalkyl ketones with (-)-diisopinocampheylchloroborane ((-)-DIP-Chloride, 1) and (-)-B-isopinocampheyl-9-borabicyclononane (R-Alpine-Borane, 2) has been made.In the case of reagent 1, the direction of asymmetric induction in the chiral reduction of aryl trifluoromethyl ketones differs from that of the corresponding mono- and difluoromethyl ketones.For example, while 2-fluoro, and 2,2-difluoroacetophenones are reduced with 1 to the R-alcohols in 95percent and 85percent ee, respectively, 2,2,2-trifluoroacetophenone is reduced, under neat conditions at room temperature, to the S-alcohol in 90percent ee.Though DIP-Chloride reduces unhindered prochiral dialkyl ketones in poor ee, alkyl α-fluoroalkyl ketones are reduced in improved ee depending on the number of α-fluorine atoms present in the ketone.While monofluoromethyl ketones provide moderate ee in the R-isomer, the di- and trifluoromethyl ketones are reduced in moderate to excellent ee in the opposite isomer.For example, 1-fluoro-2-octanone is reduced in 40percent ee (R), whereas 1,1-difluoro- and 1,1,1-trifluoro-2-octanone are reduced in 32percent (S), and 91percent ee (S), respectively.In the case of the asymmetric reduction of the above series of ketones with 2, the results are different.There is no change in the direction of chiral induction in the reduction of α-fluoroacetophenones with 2. 2-Fluoroacetophenone and 2,2-difluoroacetophenone are reduced with 2 to the R-alcohol in 89percent and 97percent ee, respectively.The reaction of 2,2,2-trifluoroacetophenone is very slow, only 90percent complete in 45 d, and provides the R-alcohol in 32percent ee.In contrast, while 1-fluoro- and 1,1-difluoro-2-octanone are reduced by 2 in 65percent (R) and 50percent ee (R), respectively, 1,1,1-trifluoro-2-octanone is reduced in 60percent ee (S), raising the question of which factors other than the steric size of the trifluoromethyl group, control the enantioselectivity of these reductions.The effect of steric versus electronic influence in such chiral reductions is discussed.

Stereo- and regiocontrolled synthesis of fluorohydrins from optically active epoxides

The hydrofluorination of optically active terminal epoxides, which were produced by a microbial reaction, with HF-amine reagents weer studied. 1,2-Epoxyoctane and glycidyl hexyl ether gave the corresponding 2-fluoro-1-alkanol derivatives with inversion of the asymmetric center with high stereospecificity, while in the hydrofluorination of pentafluorostyrene oxide and 2-methyl-1,2-epoxyhexane, partial racemization occurred. The basicity of the amine used, the HF/amine ratio in the HF-amine reagent, and the substituent on the epoxide affected the stereospecificity and regioselectivity of the hydrofluorination of the epoxides.