173901-03-6

Basic information

• Product Name: (R)-1-(Pyrid-3-yl)-2-chloroethanol
• Synonyms: (R)-1-(PYRID-3-YL)-2-CHLOROETHAN-1-OL;(R)-2-CHLORO-1-(3'-PYRIDYL)-1-ETHANOL;(R)-1-(Pyrid-3-yl)-2-chloroethanol;(S)-1-(Pyrid-3-yl)-2-chloroethanol;(R)-2-chloro-1-(pyridin-3-yl)ethanol;(1R)-2-Chloro-1-(3-pyridyl)ethanol;(R)-2-Chloro-1-(3-pyridyl)ethanol
• CAS NO: 173901-03-6
• Molecular Formula: C7H8ClNO
• Molecular Weight: 157.6
• Mol File: 173901-03-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 299.5 °C at 760 mmHg
• Flash Point: 134.9 °C
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 0.00053mmHg at 25°C
• Refractive Index: 1.557
• PKA: 12.53±0.20(Predicted)
• CAS DataBase Reference: (R)-1-(Pyrid-3-yl)-2-chloroethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(Pyrid-3-yl)-2-chloroethanol(173901-03-6)
• EPA Substance Registry System: (R)-1-(Pyrid-3-yl)-2-chloroethanol(173901-03-6)

Safety Data

• Hazardous Substances Data: 173901-03-6(Hazardous Substances Data)

Usage

Uses

(R)-2-Chloro-1-(3-pyridyl)ethanol is used in the synthetic preparation of chiral amino(pyridinyl)ethanol via lipase-mediated kinetic resolution.

InChI:InChI=1/C7H8ClNO/c8-4-7(10)6-2-1-3-9-5-6/h1-3,5,7,10H,4H2/t7-/m0/s1

Upstream product

• 55484-11-2 2-chloro-1-(pyridin-3-yl)ethan-1-one 
• 61889-48-3 2-chloro-1-(3-pyridinyl)ethanone hydrochloride 
• 350-03-8 methyl-3-pyridylketone 
• 108-05-4 vinyl acetate 

Downstream Products

• 174060-40-3 3-[(2R)-oxiranyl]pyridine 

Relevant articles and documents

A chemoenzymatic scalable route to optically active (R)-1-(pyridin-3-yl)-2- aminoethanol, valuable moiety of β3-adrenergic receptor agonists

Enantiomerically pure (R)-2-chloro-1-(pyridin-3-yl)ethanol has been prepared by kinetic resolution performed in the presence of Candida antarctica SP435-L lipase immobilized on a macroporous polyacrylate resin (Novozym 435). It was converted into (R)-1-(pyridin-3-yl)-2-aminoethanol, left-hand side of β3-adrenergic receptor ligands.

Solvent and in situ catalyst preparation impacts upon Noyori reductions of aryl-chloromethyl ketones: application to syntheses of chiral 2-amino-1-aryl-ethanols

As part of medicinal chemistry efforts we found it necessary to develop general syntheses of highly enantiomerically enriched 1-aryl-2-chloroethanols and 1-aryl-2-methylaminoethanols. A survey of literature methods suggested that a truly general approach had not yet been reported, encouraging us to undertake the development of such a methodology. This study describes the design, development, and reduction to practice of a general synthesis of chiral 1-aryl-2-chloroethanols and the transformation of these entities to highly enantiomerically enriched 1-aryl-2-methylaminoethanols. Of particular importance were observations of the impact of solvent and the method of catalyst preparation on the yield and enantiomerical excess of chlorohydrins prepared via Noyori transfer hydrogenations of aryl-chloromethyl ketones.

A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium-diamine catalyst

A practical method for the synthesis of optically active aromatic epoxides has been developed via the formation of optically active α-chlorinated alcohols and intramolecular etherification. Optically active alcohols with up to 99% ee can be obtained from