191109-51-0

Basic information

• Product Name: (S)-b-AMino-4-chloro-benzeneethanol
• Synonyms: (S)-b-AMino-4-chloro-benzeneethanol;(S)-2-aMino-2-(4-chlorophenyl)ethanol;(2S)-2-AMINO-2-(4-CHLOROPHENYL)ETHAN-1-OL;(2S)-2-Amino-2-(4-chlorophenyl)ethanol
• CAS NO: 191109-51-0
• Molecular Formula: C₈H₁₀ClNO
• Molecular Weight: 171.6241
• Mol File: 191109-51-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: (S)-b-AMino-4-chloro-benzeneethanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-b-AMino-4-chloro-benzeneethanol(191109-51-0)
• EPA Substance Registry System: (S)-b-AMino-4-chloro-benzeneethanol(191109-51-0)

Safety Data

• Hazardous Substances Data: 191109-51-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
(S)-b-Amino-4-chloro-benzeneethanol is used as a key intermediate in the synthesis of pharmaceutical drugs, particularly those targeting the adrenergic system. Its unique stereochemistry allows for the development of enantiomerically pure compounds, which can exhibit different biological activities and reduce potential side effects.
Used in Organic Synthesis:
(S)-b-Amino-4-chloro-benzeneethanol is used as a building block in organic synthesis for the preparation of various biologically active compounds. Its functional groups and chiral center enable the formation of a wide range of molecules with potential applications in medicine, agrochemistry, and other fields.
Used in Chiral Recognition Studies:
Due to its chiral nature, (S)-b-Amino-4-chloro-benzeneethanol is used as a tool for studying stereochemistry and chiral recognition in chemical and biological systems. This can help in understanding the role of chirality in molecular interactions and the development of more effective and selective drugs.
Used in Analytical Chemistry:
(S)-b-Amino-4-chloro-benzeneethanol can be employed as a chiral reference standard in analytical chemistry for the determination of enantiomeric purity and the development of chiral separation techniques, such as chromatography and capillary electrophoresis.
Used in Material Science:
The unique properties of (S)-b-Amino-4-chloro-benzeneethanol, such as its chirality and functional groups, may also find applications in the development of new materials with specific properties, such as chiral catalysts, sensors, or optically active polymers.

Upstream product

• 169272-17-7 (S)-2-azido-2-(4-chlorophenyl)ethanol 
• 1073-67-2 4-vinylbenzyl chloride 
• 152142-03-5 (1R)-1-(4-chlorophenyl)-1,2-ethanediol 
• 191109-44-1 (R)-4-(p-chlorophenyl)-1,3-dioxolane-2-one 
• 67336-19-0 (S)-2-amino-2-(4-chlorophenyl)acetic acid 
• 7477-64-7 1-(p-chlorophenyl)-1,2-ethanediol 
• 27993-56-2 1-(4-chlorophenyl)-2-hydroxyethanone 
• 2788-86-5 4-Chlorostyrene oxide 
• 179811-64-4 4-(aminomethyl)benzene-1,2-diol hydrochloride 

Downstream Products

• 191109-58-7 2-(Bis-{[(S)-1-(4-chloro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-amino)-N-[(S)-1-(4-chloro-phenyl)-2-hydroxy-ethyl]-acetamide 

Relevant articles and documents

Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase

Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.

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