70111-05-6

Basic information

• Product Name: (S)-2-CHLORO-1-PHENYL-ETHANOL
• Synonyms: (S)-2-CHLORO-1-PHENYL-ETHANOL;S(+)-2-CHLORO-1-PHENYLETHANOL;S(+)-ALPHA-(CHLOROMETHYL)BENZENEMETHANOL;(s)-(+)-α-(chloromethyl)benzenemethanol;(1S)-2-Chloro-1-phenylethanol;(alphaS)-alpha-Chloromethylbenzenemethanol;(S)-1-Phenyl-2-chloroethanol;(S)-(+)-2-chloro-1-phenylethanol (S)-2-CHLORO-1-PHENYL-ETHANOL
• CAS NO: 70111-05-6
• Molecular Formula: C₈H₉ClO
• Molecular Weight: 156.61
• Product Categories: Alcohols, Hydroxy Esters and Derivatives;Chiral Compounds
• Mol File: 70111-05-6.mol
• Article Data: 198

Chemical Properties

• Boiling Point: 255℃
• Flash Point: 113 °C
• Appearance: /
• Density: 1.185 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00869mmHg at 25°C
• Refractive Index: n20/D 1.550(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.21±0.20(Predicted)
• BRN: 3648988
• CAS DataBase Reference: (S)-2-CHLORO-1-PHENYL-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-CHLORO-1-PHENYL-ETHANOL(70111-05-6)
• EPA Substance Registry System: (S)-2-CHLORO-1-PHENYL-ETHANOL(70111-05-6)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 70111-05-6(Hazardous Substances Data)

Usage

Description

(S)-2-CHLORO-1-PHENYL-ETHANOL, also known as (S)-(+)-2-chloro-1-phenylethanol, is a chiral organic compound characterized by the presence of a chlorine atom and a phenyl group attached to a chiral carbon center. (S)-2-CHLORO-1-PHENYL-ETHANOL exhibits a specific stereochemistry, with the chlorine atom and the phenyl group positioned on the same side of the chiral carbon, resulting in the (S) configuration. It is a valuable intermediate in the synthesis of various organic and pharmaceutical compounds due to its unique structural features and reactivity.

Uses

Used in Organic Synthesis:
(S)-2-CHLORO-1-PHENYL-ETHANOL is used as a building block for the preparation of enantiopure styrene oxide, which is an important intermediate in organic synthesis. The enantiopurity of the styrene oxide ensures that the final products have the desired stereochemistry, which is crucial for their biological activity and selectivity.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (S)-2-CHLORO-1-PHENYL-ETHANOL serves as a key building block for the synthesis of enantiomerically pure drug candidates. The ability to produce enantiopure compounds is essential for the development of drugs with improved efficacy, reduced side effects, and better pharmacokinetic properties.
Used in Chiral Pool Synthesis:
(S)-2-CHLORO-1-PHENYL-ETHANOL can be employed as a chiral pool compound in the synthesis of various chiral molecules. Chiral pool synthesis is a strategy that utilizes naturally occurring chiral compounds as starting materials to construct more complex chiral molecules. This approach can lead to more efficient and environmentally friendly synthetic routes.
Used in Asymmetric Catalysis:
(S)-2-CHLORO-1-PHENYL-ETHANOL can also be used in asymmetric catalysis, a powerful tool for the enantioselective synthesis of chiral compounds. Asymmetric catalysts can selectively promote the formation of one enantiomer over the other, allowing for the production of enantiomerically pure products with high yields and selectivity.

InChI:InChI=1/C8H9ClO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6H2/t8-/m1/s1

Upstream product

• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 100-42-5 styrene 
• 108-22-5 Isopropenyl acetate 
• 1674-30-2 1-phenyl-2-chloroethanol 
• 98-86-2 acetophenone 
• 622-24-2 2-phenylethyl chloride 
• 532-27-4 1-chloroacetophenone 
• 97-72-3 2-Methylpropionic anhydride 
• 773837-37-9 sodium cyanide 
• 56751-12-3 2-chloro-1-phenylethanol 
• 69638-96-6 isopropenyl valerate 
• 108-05-4 vinyl acetate 
• 876-27-7 4-chlorophenyl acetate 
• 64-18-6 formic acid 

Downstream Products

• 177963-02-9 ((S)-2-Chloro-1-phenyl-ethoxy)-trimethyl-silane 
• 223393-84-8 (1S)-1-phenyl-2-(phenylseleno)ethanol 
• 124817-06-7 (S)-2-azido-1-phenylethanol 
• 174472-00-5 (S)-2-methoxy-2-phenylethylamine 
• 177963-03-0 ((S)-2-Azido-1-methoxy-ethyl)-benzene 
• 752258-45-0 ((S)-2-Azido-1-phenyl-ethoxy)-trimethyl-silane 
• 177963-05-2 C₁₅H₁₅N₃O 
• 177963-04-1 ((S)-2-Azido-1-cyclohexylmethoxy-ethyl)-benzene 
• 103665-43-6 (S)-1-acetoxy-1-phenyl-2-chloroethane 
• 56613-81-1 (S)-2-Amino-1-phenyl-1-ethanol 
• 65058-52-8 N-methyl (S)-2-hydroxy-2-phenylethylamine 
• 913289-36-8 (5S)-3-methyl-5-phenyl-2-oxazolidinone 
• 129157-04-6 (R)-2-t-butylamino-2-phenylethanol 
• 14467-32-4 (1S)-2-(tert-butylamino)-1-phenylethanol 

Relevant articles and documents

Unmasking the Hidden Carbonyl Group Using Gold(I) Catalysts and Alcohol Dehydrogenases: Design of a Thermodynamically-Driven Cascade toward Optically Active Halohydrins

A concurrent cascade combining the use of a gold(I) N-heterocyclic carbene (NHC) and an alcohol dehydrogenase (ADH) is disclosed for the synthesis of highly valuable enantiopure halohydrins in an aqueous medium and under mild reaction conditions. The meth

Quinone Reduction by Organo-Osmium Half-Sandwich Transfer Hydrogenation Catalysts

Organo-osmium(II) 16-electron complexes [OsII(η6-arene)(R-PhDPEN)] (where η6-arene =para-cymene or biphenyl) can catalyze the reduction of prochiral ketones to optically pure alcohols in the presence of a hydride source. Such complexes can achieve the conversion of pyruvate to unnatural http://www.w3.org/1999/xlinkd-lactate in cancer cells. To improve the catalytic performance of these osmium complexes, we have introduced electron-donor and electron-acceptor substituents (R) into thepara(R1) ormeta(R2) positions of the chiral R-phenyl-sulfonyl-diphenylethylenediamine (R-PhDPEN) ligands and explored the reduction of quinones, potential biological substrates, which play a major role in cellular electron transfer chains. We show that the series of [OsII(η6-arene)(R-PhDPEN)] derivatives exhibit high turnover frequencies, enantioselectivities (>92%), and conversions (>93%) for the asymmetric transfer hydrogenation (ATH) of acetophenone-derived substrates and reduce duroquinone and menadione to their di-alcohol derivatives. Modeling of the catalysis using density functional theory (DFT) calculations suggests a mechanism involving formic acid deprotonation assisted by the catalyst amine groups, phenyl-duroquinone stacking, hydride transfer to OsII, possible CO2coordination, and tilting of the η6-arene ring, followed by hydride transfer to the quinone. These findings not only reveal subtle differences between Ru(II) and Os(II) catalysts, but also introduce potential biological applications.

Asymmetric Catalytic Meerwein-Ponndorf-Verley Reduction of Ketones with Aluminum(III)-VANOL Catalysts

We report herein an efficient aluminum-catalyzed asymmetric MPV reduction of ketones with broad substrate scope and excellent yields and enantiomeric inductions. A variety of aromatic (both electron-poor and electron-rich) and aliphatic ketones were converted to chiral alcohols in good yields with high enantioselectivities (26 examples, 70-98percent yield and 82-99percent ee). This method operates under mild conditions (-10 °C) and low catalyst loading (1-5 mol percent). Furthermore, this process is catalyzed by the earth-abundant main-group element aluminum and employs 2-propanol as the hydride source.