140632-12-8

Basic information

• Product Name: (S)-(-)-1-(2-Bromophenyl)ethylamine
• Synonyms: (S)-(-)-1-(2-Bromophenyl)ethylamine;Benzenemethanamine, 2-bromo-α-methyl-, (αS)-;(S)-2-Bromo-alpha-methylbenzenemethanamine;(1S)-1-(2-BROMOPHENYL)ETHAN-1-AMINE
• CAS NO: 140632-12-8
• Molecular Formula: C₈H₁₀BrN
• Molecular Weight: 200.08
• Product Categories: API intermediates
• Mol File: 140632-12-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 143-146℃
• Boiling Point: 249℃
• Flash Point: 104℃
• Appearance: /
• Density: 1.400
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.50±0.10(Predicted)
• CAS DataBase Reference: (S)-(-)-1-(2-Bromophenyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1-(2-Bromophenyl)ethylamine(140632-12-8)
• EPA Substance Registry System: (S)-(-)-1-(2-Bromophenyl)ethylamine(140632-12-8)

Safety Data

• Hazardous Substances Data: 140632-12-8(Hazardous Substances Data)

Usage

General Description

(S)-(-)-1-(2-Bromophenyl)ethylamine, also known as (S)-(-)-2-phenethylamine or (S)-(-)-alpha-methyl-2-phenethylamine, is an organic compound with the chemical formula C8H10BrN. It is a chiral amine and a derivative of phenethylamine, with a bromine atom attached to the phenyl ring. (S)-(-)-1-(2-Bromophenyl)ethylamine is commonly used as a starting material in the synthesis of various pharmaceuticals and research chemicals. It has also been investigated for its potential therapeutic properties, including its role as a potential antipsychotic agent. Additionally, (S)-(-)-1-(2-Bromophenyl)ethylamine has been used in the production of certain pesticides and herbicides. Due to its structural and biochemical properties, this compound is of interest to researchers in the field of medicinal chemistry and chemical biology.

Upstream product

• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 2142-69-0 2-bromophenyl methyl ketone 
• 109-73-9 N-butylamine 
• 5411-56-3 1-(2-bromophenyl)ethanol 
• 87227-77-8 bishydrochloride salt of cis-1,4-diamino-but-2-ene 
• 1434602-33-1 (E)-1-(2-bromophenyl)ethanone O-benzyloxime 
• 5411-56-3 (1R)-1-(2-bromophenyl)ethan-1-ol 
• 943779-19-9 1-((S)-1-Azido-ethyl)-2-bromo-benzene 

Downstream Products

• 943779-20-2 C₃₆H₃₇BrN₆O₃S 
• 927175-30-2 2-[1-(2-bromo-phenyl)-ethylamino]-5-isopropyl-thiazol-4-one 
• 927175-29-9 [1-(2-bromo-phenyl)-ethyl]-thiourea 

Relevant articles and documents

n-Butylamine as an alternative amine donor for the stereoselective biocatalytic transamination of ketones

Formal reductive amination has been a main focus of biocatalysis research in recent times. Among the enzymes able to perform this transformation, pyridoxal-5′-phosphate-dependent transaminases have shown the greatest promise in terms of extensive substrate scope and industrial application. Despite concerted research efforts in this area, there exist relatively few options regarding efficient amino donor co-substrates capable of allowing high conversion and atom efficiency with stable enzyme systems. Herein we describe the implementation of the recently described spuC gene, coding for a putrescine transaminase, exploiting its unusual amine donor tolerance to allow use of inexpensive and readily-available n-butylamine as an alternative to traditional methods. Via the integration of SpuC homologues with tandem co-product removal and cofactor regeneration enzymes, high conversion could be achieved with just 1.5 equivalents of the amine with products displaying excellent enantiopurity.

Stereoselective amination of racemic sec-alcohols through sequential application of laccases and transaminases

A one-pot/two-step bienzymatic asymmetric amination of secondary alcohols is disclosed. The approach is based on a sequential strategy involving the use of a laccase/TEMPO catalytic system for the oxidation of alcohols into ketone intermediates, and their following transformation into optically enriched amines by using transaminases. Individual optimizations of the oxidation and biotransamination reactions have been carried out, studying later their applicability in a concurrent process. Therefore, 17 racemic (hetero) aromatic sec-alcohols with different substitutions in the aromatic ring have been converted into enantioenriched amines with good to excellent selectivities (90-99% ee) and conversion values (67-99%). The scalability of the process was also demonstrated when two different amine donors were used in the transamination step, such as isopropylamine and cis-2-buten-1,4-diamine. Satisfyingly, both sacrificial amine donors can shift the equilibrium toward the amine formation, leading to the corresponding isolated enantioenriched amines with good to excellent results.

But-2-ene-1,4-diamine and But-2-ene-1,4-diol as Donors for Thermodynamically Favored Transaminase- and Alcohol Dehydrogenase-Catalyzed Processes

Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78–99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91–99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products. (Figure presented.).