176707-77-0

Basic information

• Product Name: (R)-1-(3-Bromophenyl)ethylamine
• Synonyms: (R)-3-BROMO-ALPHA-METHYLBENZYLAMINE;(R)-(+)-3-BROMO A-METHYLBENZYLAMINE;(R)-1-(3-BROMOPHENYL)ETHANAMINE;(R)-1-(3-BROMOPHENYL)ETHYLAMINE;[(1R)-1-(3-Bromophenyl)ethyl]amine;(R)-1-(3-Bromophenyl)ethylamine, ChiPros 99%, ee 98+%;Benzenemethanamine, 3-bromo-α-methyl-, (αR)-;Albb-005066
• CAS NO: 176707-77-0
• Molecular Formula: C₈H₁₀BrN
• Molecular Weight: 200.08
• Product Categories: API intermediates
• Mol File: 176707-77-0.mol

Chemical Properties

• Boiling Point: 96°C/4mm
• Flash Point: 96°C/4mm
• Appearance: /
• Density: 1.33
• Vapor Pressure: 0.024mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive: Air Sensitive
• CAS DataBase Reference: (R)-1-(3-Bromophenyl)ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3-Bromophenyl)ethylamine(176707-77-0)
• EPA Substance Registry System: (R)-1-(3-Bromophenyl)ethylamine(176707-77-0)

Safety Data

• Hazard Codes: C,N
• Statements: 34-51/53-43-22
• Safety Statements: 26-36/37/39-61-45
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 176707-77-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(3-Bromophenyl)ethylamine is used as a precursor for the synthesis of various pharmaceuticals and research chemicals. Its chiral nature and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
(R)-1-(3-Bromophenyl)ethylamine is used as an intermediate in the production of other organic compounds, contributing to the synthesis of a wide range of chemical products.
Used in Drug Development:
Due to its structural properties, (R)-1-(3-Bromophenyl)ethylamine has potential applications in the development of new drugs and therapeutic agents, aiding in the advancement of chemical and pharmaceutical research.

InChI:InChI=1/C8H10BrN/c1-6(10)7-3-2-4-8(9)5-7/h2-6H,10H2,1H3

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 74877-08-0 1-(3-bromophenyl)ethanamine 
• 623-50-7 ethyl 2-hydroxyacetate 
• 95-92-1 oxalic acid diethyl ester 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 108-22-5 Isopropenyl acetate 
• 2142-63-4 1-(3-Bromophenyl)ethanone 
• 18523-22-3 2,3'-dibromoacetophenone 
• 1434602-84-2 (Z)-1-(3-bromophenyl)ethanone oxime 
• 1434603-05-0 (Z)-1-(3-bromophenyl) ethanone O-benzyloxime 
• 24280-05-5 N-[1-(3-bromophenyl)ethylidene]hydroxyl amine 
• 87227-77-8 bishydrochloride salt of cis-1,4-diamino-but-2-ene 
• 52780-14-0 1-(3-bromophenyl)ethanol 
• 110-60-1 1,4-diaminobutane 

Downstream Products

• 1187932-25-7 (R)-tert-butyl (1-(3-bromophenyl)ethyl)carbamate 
• 1381809-17-1 (E)-(2R,5S,11S,14S,17R,18R)-11-(3-hydroxy-benzyl)-14-isopropyl-18-methoxy-2,17-dimethyl-3,9,12,15,28-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone 
• 1381813-33-7 [(R)-1-(3-vinyl-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 1381813-39-3 (R)-1-(3-vinylphenyl)ethylamine hydrochloride 
• 1381813-48-4 (S)-1-{(S)-3-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-[(S)-2-((2R,3R)-3-methoxy-2-methyl-hept-6-enoylamino)-3-methyl-butyrylamino]-propionyl}-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(3-vinyl-phenyl)-ethyl]-amide 
• 1381813-63-3 (E)-(2R,5S,11S,14S,17R,18R)-11-[3-(tert-butyl-dimethyl-silanyloxy)-benzyl]-14-isopropyl-18-methoxy-2,17-dimethyl-3,9,12,15,28-pentaaza-tricyclo[21.3.1.1*5,9*]octacosa-1⁽²⁷⁾,21,23,25-tetraene-4,10,13,16-tetraone 
• 1429187-89-2 (R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate 
• 1429187-97-2 (R)-N-(1-(3-bromophenyl)ethyl)-3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide 

Relevant articles and documents

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.

Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases

The discovery and characterisation of enzymes with both monoamine and diamine transaminase activity is reported, allowing conversion of a wide range of target ketone substrates with just a small excess of amine donor. The diamine co-substrates (putrescine, cadaverine or spermidine) are bio-derived and the enzyme system results in very little waste, making it a greener strategy for the production of valuable amine fine chemicals and pharmaceuticals.

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.).

PROCESS FOR THE PREPARATION OF CHIRAL AMINES FROM PROCHIRAL KETONES

There is provided a method for the preparation of an enantiomerically enriched amine from a prochiral ketone.

PROCESS FOR THE PREPARATION OF CHIRAL AMINES BY ASYMMETRIC HYDROGENATION OF PROCHIRAL OXIMES

There is provided a method for the preparation of an enantiomerically enriched amine by asymmetric hydrogenation of a prochiral oxime.

Monoamine oxidase-ω-transaminase cascade for the deracemisation and dealkylation of amines

Herein we report a one-pot protocol for the deracemisation of chiral benzylic amines employing a novel monoamine oxidase-ω-transaminase cascade, allowing access to enantiopure compounds in >99 % ee. We also demonstrate that the same enzymatic cascade can be employed for the dealkylation of secondary amines with >99 % conversion. Cascade ball: A monoamine oxidase- ω-transaminase cascade has been developed for the deracemisation of chiral benzylic amines, allowing access to the enantiopure compounds in >99 % ee. The same system was also employed for the efficient dealkylation of secondary amines.

Transaminases applied to the synthesis of high added-value enantiopure amines

Critical parameters affecting the stereoselective amination of (hetero)aromatic ketones using transaminases have been studied, such as temperature, pH, substrate concentration, cosolvent, and source and percentage of amino donor, to further optimize the production of enantiopure amines using both (S)- and (R)-selective biocatalysts from commercial suppliers. Interesting enantiopure amino building blocks have been obtained, overcoming some limitations of traditional chemical synthetic methods. Representative processes were scaled up, affording halogenated and heteroaromatic amines in enantiomerically pure form and good isolated yields.

Asymmetric synthesis of nonracemic primary amines via spiroborate-catalyzed reduction of pure (E)- and (Z)-O-benzyloximes: Applications toward the synthesis of calcimimetic agents

Highly enantiopure (1-aryl)- and (1-naphthyl)-1-ethylamines were synthesized by the borane-mediated reduction of single-isomeric (E)- and (Z)-O-benzyloxime ethers using the stable spiroborate ester derived from (S)-diphenyl valinol and ethylene glycol as the chiral catalyst. Primary (R)-arylethylamines were prepared by the reduction of pure (Z)-ethanone oxime ethers in up to 99% ee using 15% of catalyst. Two convenient and facile approaches to the synthesis of new and known calcimimetic analogues employing enantiopure (1-naphthalen-1-yl)ethylamine as chiral precursor are described.

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine

An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.

Organocatalytic asymmetric biomimetic transamination of aromatic ketone to optically active amine

An asymmetric biomimetic transamination of aromatic ketones to optically active amines with o-HOPhCH2NH2 as amine source catalyzed by hydroquinine-derived chiral base is described. Up to 85% ee was obtained.