128535-89-7

Basic information

• Product Name: (S)-2-Amino-1-(4-chlorophenyl)ethanol
• Synonyms: (S)-2-Amino-1-(4-chlorophenyl)ethanol;(+)-a-(Aminomethyl)-p-chlorobenzyl alcohol
• CAS NO: 128535-89-7
• Molecular Formula: C₈H₁₀ClNO
• Molecular Weight: 171.6241
• Product Categories: API intermediates
• Mol File: 128535-89-7.mol

Chemical Properties

• Boiling Point: 319.8 °C at 760 mmHg
• Flash Point: 147.2 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 0.000138mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: (S)-2-Amino-1-(4-chlorophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Amino-1-(4-chlorophenyl)ethanol(128535-89-7)
• EPA Substance Registry System: (S)-2-Amino-1-(4-chlorophenyl)ethanol(128535-89-7)

Safety Data

• Hazardous Substances Data: 128535-89-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Amino-1-(4-chlorophenyl)ethanol is used as a pharmaceutical intermediate for the synthesis of biologically active molecules. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic effects.
Used in Chemical Industry:
In the chemical industry, (S)-2-Amino-1-(4-chlorophenyl)ethanol serves as a building block for the synthesis of complex organic molecules. Its versatile structure makes it a valuable precursor in the creation of various chemical compounds.
Used in Production of Chiral Catalysts:
(S)-2-Amino-1-(4-chlorophenyl)ethanol is utilized in the production of chiral catalysts, which are essential in asymmetric synthesis and other chemical reactions requiring stereoselectivity. Its chiral nature contributes to the development of enantioselective catalysts.
Used in Medicinal Applications:
(S)-2-Amino-1-(4-chlorophenyl)ethanol has been studied for its potential as a neuroprotective agent, indicating its use in the treatment or prevention of neurological disorders. Its protective effects on neurons could be beneficial in managing conditions associated with neuronal damage.
Additionally, (S)-2-Amino-1-(4-chlorophenyl)ethanol has been investigated for its potential as an anticancer agent, suggesting its use in cancer therapy. It may contribute to the development of novel treatments targeting cancer cells while minimizing damage to healthy cells.

InChI:InChI=1/C8H10ClNO/c9-7-3-1-6(2-4-7)8(11)5-10/h1-4,8,11H,5,10H2

Upstream product

• 149285-94-9 Acetic acid (S)-2-acetylamino-1-(4-chloro-phenyl)-ethyl ester 
• 297765-49-2 (S)-(+)-2-azido-1-(p-chlorophenyl)ethanol 
• 2788-86-5 (2S)-2-(4-chlorophenyl)oxirane 
• 1073-67-2 4-vinylbenzyl chloride 
• 104-88-1 4-chlorobenzaldehyde 
• 357952-84-2 (S)-(+)-1-(4-Chlorophenyl)-2-(p-tolylsulfonyloxy)ethanol 
• 6660-08-8 N-(2-(4-chlorophenyl)-2-oxoethyl)acetamide 
• 149342-40-5 N-(4-chloro-β-hydroxy-phenethyl)-acetamide 
• 5467-71-0 4-chlorophenacylamine hydrochloride 
• 26086-60-2 2-azido-4'-chloroacetophenone 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Relevant articles and documents

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Asymmetric reduction of α-keto aldoxime o -ethers

The catalytic asymmetric reduction of -keto aldoxime O-methyl, O-benzyl, and O-trityl ethers, derived from substituted acetophenones, with borane/oxazaborolidines, by transfer hydrogenation, and with yeast, was studied. The reduction with borane/oxazaborolidines produced the corresponding -hydroxy oxime ethers, -hydroxy hydroxylamine ethers, and -amino alcohols in 39-78% yields and up to 77% ee. The carbonyl group was selectively reduced by transfer hydrogenation with formic acid-triethylamine catalyzed by RhCl[(R,R)-TsDPEN](Ce, and also with yeast, producing -hydroxy oxime ethers, up to 75% ee and 93% ee, respectively. Georg Thieme Verlag Stuttgart New York.

Synthesis of enantiopure 2-amino-1-phenyl and 2-amino-2-phenyl ethanols using enantioselective enzymatic epoxidation and regio- and diastereoselective chemical aminolysis

Several enantiopure 1,2-amino alcohols have been prepared by combining a stereoselective enzymatic epoxidation of styrenes with regio- and stereoselective chemical reactions. An interesting reactivity has been noted concerning the reaction of epoxides and NH3 under microwave activation.

Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline

A very convenient and highly efficient synthesis of near enantiopure β-azido and β-amino alcohols including biologically active substances such as (R)-octopamine, (R)-tembamide and (R)-aegeline from optically active 1,2-diol monotosylates is reported.

Baker's Yeast Reduction of α-(Acylamino)acetophenones and Lipase Catalyzed Resolution of 2-Acylamino-1-arylethanols

Enzymatic reduction of α-acylaminoacetophenones with fermenting baker's yeast afforded optically active (R)-2-acylamino-1-arylethanols.Furthermore, lipase-catalyzed resolution of the 2-acylamino-1-arylethanols using vinyl acetate as an acyl donor resulted in the formation of (S)-1-acetoxy-2-acylamino-1-arylethanols and (R)-2-acylamino-1-arylethanols.