27298-97-1

Basic information

• Product Name: (S)-(-)-4-Bromo-alpha-phenylethylamine
• Synonyms: (S)-(-)-p-Bromo-alpha-methylbenzylamine;(S)-(-)-P-BROMO-ALPHA-PHENETHYLAMINE;(S)-(-)-1-AMINO-1-(4-BROMOPHENYL)ETHANE;(S)-1-(4-BROMOPHENYL)ETHANAMINE;(S)-(-)-1-(4-BROMOPHENYL)ETHYLAMINE;(S)-1-(4-BROMOPHENYL)ETHYLAMINE;S(-)-4-BROMO-ALPHA-METHYLBENZYLAMINE;(S)-(-)-4-BROMO-ALPHA-PHENYLETHYLAMINE
• CAS NO: 27298-97-1
• Molecular Formula: C₈H₁₀BrN
• Molecular Weight: 200.08
• EINECS: -0
• Product Categories: chiral;API intermediates;Chiral Compound
• Mol File: 27298-97-1.mol

Chemical Properties

• Melting Point: -25°C
• Boiling Point: 63-72 °C (0.2 mmHg)
• Flash Point: >110°C
• Appearance: colorless to light yellow liquid
• Density: 1.390 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0134mmHg at 25°C
• Refractive Index: n20/D 1.566
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.82±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 5729988
• CAS DataBase Reference: (S)-(-)-4-Bromo-alpha-phenylethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-Bromo-alpha-phenylethylamine(27298-97-1)
• EPA Substance Registry System: (S)-(-)-4-Bromo-alpha-phenylethylamine(27298-97-1)

Safety Data

• Hazard Codes: C,N
• Statements: 34-51/53-43-20/22
• Safety Statements: 26-28-36/37/39-45-61
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-23
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 27298-97-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-4-Bromo-alpha-phenylethylamine is used as a key raw material in organic synthesis for the creation of various compounds.
Used in Pharmaceutical Industry:
(S)-(-)-4-Bromo-alpha-phenylethylamine is used as an intermediate in the pharmaceutical industry for the synthesis of specific drugs.
Used in Agrochemical Industry:
(S)-(-)-4-Bromo-alpha-phenylethylamine is also utilized as an intermediate in the agrochemical industry for the development of various agrochemical products.
Used in Synthesis of P2X7 Receptor Antagonist:
(S)-(-)-4-Bromo-alpha-phenylethylamine may be used in the synthesis of (S)-1-(1-(4-bromophenyl) ethyl)-2-cyano-3-(quinoline-5-yl) guanidine, which is an intermediate to prepare a potent and selective antagonist and radioligand for rat P2X7 receptors. This application is particularly relevant in the field of neuroscience and pharmacology, where P2X7 receptor antagonists have potential therapeutic applications in various conditions, such as neurodegenerative diseases and chronic pain.

InChI:InChI=1/C8H10BrN/c1-6(10)7-2-4-8(9)5-3-7/h2-6H,10H2,1H3/p+1/t6-/m0/s1

Upstream product

• 131214-13-6 (2R,1'R)-2-<<1'-(4-bromophenyl)ethyl>amino>-2-phenylethanol 
• 99-90-1 para-bromoacetophenone 
• 24358-62-1 1-(4-bromophenyl)ethylamine 
• 871720-04-6 (R)-N-(1-(4-bromophenyl)ethyl)-2,2,2-trifluoroacetamide 
• 220441-76-9 (R)-2-(4-Bromo-phenyl)-4-phenyl-oxazolidine 
• 1122-91-4 4-bromo-benzaldehyde 
• 99-73-0 para-bromophenacyl bromide 
• 71426-51-2 anti-α,4'-dibromoacetophenone oxime 
• 1434603-04-9 (Z)-1-(4-bromophenyl)ethanone O-benzyloxime 
• 1585-07-5 1-bromo-4-ethylbenzene 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 182141-70-4 N-[(1S)-1-(4-bromophenyl)ethyl]-2,2,2-trifluoroacetamide 
• 2354-91-8 (S)-2,2,2-trifluoro-(α-methylbenzyl)acetamide 
• 17640-21-0 isopropyl methoxyacetate 

Downstream Products

• 186296-23-1 (S)-N-(1-(4-bromophenyl)ethyl)acetamide 
• 656237-73-9 N-[(1R)-1-(4-bromophenyl)ethyl]-4-methyl-3-nitropyridin-2-amine 
• 149552-52-3 (+)-(1S)-1-(4-bromophenyl)ethyl isocyanate 
• 578729-21-2 [(R)-1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis method of garafloxacin intermediate

The invention discloses a synthesis method of a garafloxacin intermediate (1R)-5-bromo-2, 3-dihydro-1-methyl-1H-isoindole; the synthesis method comprises the following steps of: taking a garafloxacin intermediate as a raw material; the method comprises the following steps: step 1, by taking R(+)-alpha-phenylethylamine as a raw material and lewis acid as a catalyst, carrying out bromine bromination reaction to obtain a compound 2; 2, placing the compound 2 in a solvent, adding hydrochloric acid, paraformaldehyde and a catalyst, and carrying out chloromethylation reaction to obtain a compound 3; 3, dissolving the compound 3 in a solvent, adding alkali, and heating the mixture for reaction to obtain a compound 1. The method is simple in reaction, short in route, less in three wastes, environment-friendly, high in yield of each step, less in waste of raw materials and reagents, and especially suitable for industrial production.

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented.

Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization

In recent years, the reductive amination of ketones in the presence of amine dehydrogenases emerged as an attractive synthetic strategy for the enantioselective preparation of amines starting from ketones, an ammonia source, a reducing reagent and a cofactor, which is recycled in situ by means of a second enzyme. Current challenges in this field consists of providing a broad synthetic platform as well as process development including enzyme immobilization. In this contribution these issues are addressed. Utilizing the amine dehydrogenase EsLeuDH-DM as a mutant of the leucine dehydrogenase from Exigobacterium sibiricum, a range of aryl-substituted ketones were tested as substrates revealing a broad substrate tolerance. Kinetics as well as inhibition effects were also studied and the suitability of this method for synthetic purpose was demonstrated with acetophenone as a model substrate. Even at an elevated substrate concentration of 50 mM, excellent conversion was achieved. In addition, the impact of water-miscible co-solvents was examined, and good activities were found when using DMSO of up to 30% (v/v). Furthermore, a successful immobilization of the EsLeuDH-DM was demonstrated utilizing a hydrophobic support and a support for covalent binding, respectively, as a carrier.

Mapping the substrate scope of monoamine oxidase (MAO-N) as a synthetic tool for the enantioselective synthesis of chiral amines

A library of 132 racemic chiral amines (α-substituted methylbenzylamines, benzhydrylamines, 1,2,3,4-tetrahydronaphthylamines (THNs), indanylamines, allylic and homoallylic amines, propargyl amines) was screened against the most versatile monoamine oxidase (MAO-N) variants D5, D9 and D11. MAO-N D9 exhibited the highest activity for most substrates and was applied to the deracemisation of a comprehensive set of selected primary amines. In all cases, excellent enantioselectivity was achieved (e.e. >99%) with moderate to good yields (55–80%). Conditions for the deracemisation of primary amines using a MAO-N/borane system were further optimised using THN as a template addressing substrate load, nature of the enzyme preparation, buffer systems, borane sources, and organic co-solvents.

Optimization of 2-alkoxyacetates as acylating agent for enzymatic kinetic resolution of chiral amines

In this study, the activity of acetic acid esters modified with electron withdrawing 2-alkoxy-groups was investigated as acylating agent in kinetic resolution (KR) of racemic amines. A homologous series of the isopropyl esters of four 2-alkoxyacetic acids (2-methoxy-, 2-ethoxy-, 2-propoxy- and 2-butoxyacetic acids) were prepared and investigated for enantiomer selective N-acylation, catalyzed by lipase B from Candida antarctica, under batch and continuous-flow conditions. In the first set of experiments, isopropyl 2-propoxyacetate showed the highest effectivity with all of the four racemic amines [(±)-1-phenylethylamine, (±)-4-phenylbutan-2-amine, (±)-heptan-2-amine and (±)-1-methoxypropane-2-amine] in the set enabling excellent conversions (≥46%) and enantiomeric excess values (ee ≥ 99%) with each amines in continuous-flow mode KRs under the optimized reaction conditions. In a second set of experiments, KRs of five additional amines – being substituted derivatives of (±)-1-phenylethylamine – further demonstrated the usefulness of isopropyl 2-propoxyacetate – being the best acylating agent in the first set of KRs – in KRs leading to (R)-N-propoxyacetamides with high ee values (≥99.8%).

Synthesis and pKa determination of new enantiopure dimethyl-substituted acridino-crown ethers containing a carboxyl group: Useful candidates for enantiomeric recognition studies

New enantiopure dimethyl-substituted acridino-18-crown-6 and acridino-21-crown-7 ethers containing a carboxyl group at position 9 of the acridine ring [(S,S)-8, (S,S)-9, (R,R)-10] were synthesized. The pKa values of the new crown ethers [(S,S)-8, (S,S)-9, (R,R)-10] and of an earlier reported macrocycle [(R,R)-2] were determined by UV-pH titrations. Crown ether (S,S)-8 was attached to silica gel by covalent bonds and the enantiomeric separation ability of the newly prepared chiral stationary phase [(S,S)-CSP-12] was studied by high-performance liquid chromatography (HPLC). Homochiral preference was observed and the best separation was achieved for the enantiomers of 1-NEA. Ligands (S,S)-9 and (R,R)-10 are precursors of enantioselective sensor and selector molecules for the enantiomers of protonated primary amines, amino acids, and their derivatives.

A (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline and its preparation method and application (by machine translation)

The present invention provides a kind of (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline and its preparation method and application, (R)- 4 - bromo - α - phenethylamine in under the action of Lewis acid poly formaldehyde reaction, to obtain the (R)- 5 - bromo - 1 - methyl isobutyl ketone indoline, and then using the tert-butoxy carbonyl amino can be obtained by protecting the (R)- N - Boc - 5 - bromo - 1 - methyl isobutyl ketone indoline, the ring method step is novel and unique, easy operation, the yield is higher. The use of split reagent first split to get chiral raw materials for preparing (R)- 4 - bromo - α - phenethylamine, and then prepare to obtain (R)- 5 - bromo - 1 - methyl isobutyl ketone indoline, makes it possible to greatly reduce the quantity, the quantity is greatly reduced, the whole process of splitting of waste is greatly reduced. The whole of this invention the method of preparing the raw materials are easy, simple process operation, low cost, and has relatively high practical application value. (by machine translation)

Whole-Cell Biocatalysts for Stereoselective C-H Amination Reactions

Enantiomerically pure chiral amines are ubiquitous chemical building blocks in bioactive pharmaceutical products and their synthesis from simple starting materials is of great interest. One of the most attractive strategies is the stereoselective installation of a chiral amine through C-H amination, which is a challenging chemical transformation. Herein we report the application of a multienzyme cascade, generated in a single bacterial whole-cell system, which is able to catalyze stereoselective benzylic aminations with ee values of 97.5 %. The cascade uses four heterologously expressed recombinant enzymes with cofactors provided by the host cell and isopropyl amine added as the amine donor. The cascade presents the first example of the successful de novo design of a single whole-cell biocatalyst for formal stereoselective C-H amination.

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.

A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters

A novel one-pot protocol combining aza-Michael addition and aminolysis resolution was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled-up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large-scale production of chiral β-amino acid esters. A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.