121652-86-6

Basic information

• Product Name: (R)-1-(3-CHLOROPHENYL)-1-HYDROXY-2-AMINOETHANE
• Synonyms: (R)-1-(3-CHLOROPHENYL)-1-HYDROXY-2-AMINOETHANE;Benzenemethanol,|á-(aminomethyl)-3-chloro-,(aR)-
• CAS NO: 121652-86-6
• Molecular Formula: C₈H₁₀ClNO
• Molecular Weight: 171.6241
• Mol File: 121652-86-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 319.8 °C at 760 mmHg
• Flash Point: 147.2 °C
• Appearance: /
• Density: 1.26 g/cm³
• PKA: 11.77±0.35(Predicted)
• CAS DataBase Reference: (R)-1-(3-CHLOROPHENYL)-1-HYDROXY-2-AMINOETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3-CHLOROPHENYL)-1-HYDROXY-2-AMINOETHANE(121652-86-6)
• EPA Substance Registry System: (R)-1-(3-CHLOROPHENYL)-1-HYDROXY-2-AMINOETHANE(121652-86-6)

Safety Data

• Hazardous Substances Data: 121652-86-6(Hazardous Substances Data)

Usage

General Description

(R)-1-(3-chlorophenyl)-1-hydroxy-2-aminoethane, also known as (R)-norepinephrine, is a chemical compound that functions as a neurotransmitter in the sympathetic nervous system. It is a catecholamine hormone and neurotransmitter that helps regulate blood pressure, heart rate, and the "fight-or-flight" response. (R)-norepinephrine is synthesized in the adrenal medulla and sympathetic nerve terminals and acts on alpha and beta adrenergic receptors to generate physiological responses. It is also involved in mood regulation and has been implicated in conditions such as depression and anxiety. Additionally, (R)-norepinephrine is used as a medication to treat low blood pressure and heart failure.

Upstream product

• 20697-04-5 (R)-meta-chlorostyrene oxide 
• 859931-64-9 (R)-3-chloromandelamide 
• 587-04-2 m-Chlorobenzaldehyde 
• 650638-45-2 (2R)-2-(3-chlorophenyl)-2-trimethylsilyloxyacetonitrile 

Downstream Products

• 138908-48-2 3-chloroalpha-(((2-(3,4-dimethoxyphenyl)-1-methylethyl)amino)methyl)-benzenemethanol 
• 198276-67-4 5-{2-[2-(3-Chloro-phenyl)-2(R)-hydroxy-ethylamino]-propyl}-1-phenylacetyl-1,3-dihydro-indole-2,2-dicarboxylic acid dimethyl ester 
• 1269928-33-7 (S)-tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate 

Relevant articles and documents

Aminoheteroaryl benzamides as kinase inhibitors

The present invention provides a compound of Formula (I) or a salt thereof; and therapeutic uses of these compounds. The present invention further provides pharmaceutical compositions comprising these compounds, and compositions comprising these compounds with a therapeutic co-agent.

Application of the lewis acid-lewis base bifunctional asymmetric catalysts to pharmaceutical syntheses: Stereoselective chiral building block syntheses of human immunodeficiency virus (HIV) protease inhibitor and β3- adenergic receptor agonist

Chiral building block syntheses of promising drugs were achieved using two types of catalytic stereoselective cyanosilylations of aldehydes promoted by Lewis acid-Lewis base bifunctional catalysts 1 and 2 as the key steps (diastereoselective cyanosilylation of amino aldehyde and enantioselective cyanosilylation). In the first part of this article, syntheses of chiral building blocks (6) of Atazanavir (3: human immunodeficiency virus (HIV) protease inhibitor) using the bifunctional catalyst 2 are discussed. The reaction of Boc-protected phenylalaninal 21 in the presence of 1 mol% catalyst 2 selectively afforded the anti isomer 22 as the major product (diastereomeric ratio=97:3), which was successively converted to the corresponding epoxide 6 in six steps. In the second part, we describe a chiral building block synthesis of β3-adrenergic receptor agonists. The enantioselective cyanosilylation of 3-chlorobenzaldehyde (38) with 9 mol% catalyst 1 gave the chiral cyanohydrin 39, which was converted to β-hydroxyethylamine 40 by reduction. Moreover, the chiral ligand of catalyst 1 could be recovered without column chromatography and reused without decreasing its activity.