6150-01-2

Basic information

• Product Name: (R)-1-Phenylbutylamine
• Synonyms: (R)-1-PHENYLBUTYLAMINE;(R)-1-Phenylbutylamine, ChiPros 98%, ee 98+%;(R)-1-phenylbutan-1-aMine;(R)-1-PhenylbutylaMine, ChiPros|r, 98%, ee 98+%;(R)-1-PHENYLBUTYLAMINE-HCl;(1R)-1-phenylbutan-1-amine
• CAS NO: 6150-01-2
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• Mol File: 6150-01-2.mol
• Article Data: 22

Chemical Properties

• Boiling Point: 220°C
• Flash Point: 220°C
• Appearance: /
• Density: 0.934g/cm³
• Vapor Pressure: 0.0938mmHg at 25°C
• Refractive Index: 1.52
• PKA: 9.31±0.10(Predicted)
• CAS DataBase Reference: (R)-1-Phenylbutylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Phenylbutylamine(6150-01-2)
• EPA Substance Registry System: (R)-1-Phenylbutylamine(6150-01-2)

Safety Data

• Hazard Codes: C
• Statements: 34-52/53
• Safety Statements: 26-36/37/39-45-61
• RIDADR: UN2735
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6150-01-2(Hazardous Substances Data)

Usage

General Description

(R)-1-Phenylbutylamine is a chiral amine with the chemical formula C10H15N. It is also known as phenylbutylamine or PBA and is a psychoactive drug with stimulant effects. (R)-1-Phenylbutylamine is most commonly used as a research chemical and is not approved for medical use. It is structurally related to amphetamines and is believed to exert its effects by increasing the levels of certain neurotransmitters in the brain, such as dopamine and norepinephrine. It is often used as a reference standard for analytical testing and research purposes. However, due to its psychoactive properties, it is considered a controlled substance in some jurisdictions and its use is strictly regulated.

InChI:InChI=1/C10H15N/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8,10H,2,6,11H2,1H3/t10-/m1/s1

Upstream product

• 614-14-2 1-Phenyl-1-butanol 
• 2941-19-7 1-phenyl-butylamine 
• 495-40-9 propiophenone 
• 1315613-42-3 C₁₄H₂₃NOS 
• 100-52-7 benzaldehyde 
• 566950-10-5 (R)-2-Phenyl-2-((R)-1-phenyl-buta-2,3-dienylamino)-ethanol 
• 566949-99-3 (R)-[(R)-2-methoxy-1-phenylethyl]-(1-phenylbuta-2,3-dienyl)amine 
• 144302-38-5 (R)-benzylidene-(2-methoxy-1-phenylethyl)amine 
• 741681-30-1 (R)-2-[(phenylmethylene)amino]-2-phenylacetamide 
• 22135-49-5 (S)-1-phenylbutan-1-ol 
• 386747-26-8 (R)-2-Phenyl-2-((R)-1-phenyl-but-3-enylamino)-acetamide 
• 566950-11-6 (+)-(R)-1-phenylbuta-2,3-dien-1-ylamine 
• 402750-57-6 (E)-1-phenylbutanone O-benzyl oxime 
• 206768-81-2 (R)-benzyl-(1-phenyl-but-3-enyl)-amine 

Downstream Products

• 495-40-9 propiophenone 

Relevant articles and documents

A Simple Biosystem for the High-Yielding Cascade Conversion of Racemic Alcohols to Enantiopure Amines

The amination of racemic alcohols to produce enantiopure amines is an important green chemistry reaction for pharmaceutical manufacturing, requiring simple and efficient solutions. Herein, we report the development of a cascade biotransformation to aminate racemic alcohols. This cascade utilizes an ambidextrous alcohol dehydrogenase (ADH) to oxidize a racemic alcohol, an enantioselective transaminase (TA) to convert the ketone intermediate to chiral amine, and isopropylamine to recycle PMP and NAD+ cofactors via the reversed cascade reactions. The concept was proven by using an ambidextrous CpSADH-W286A engineered from (S)-enantioselective CpSADH as the first example of evolving ambidextrous ADHs, an enantioselective BmTA, and isopropylamine. A biosystem containing isopropylamine and E. coli (CpSADH-W286A/BmTA) expressing the two enzymes was developed for the amination of racemic alcohols to produce eight useful and high-value (S)-amines in 72–99 % yield and 98–99 % ee, providing with a simple and practical solution to this type of reaction.

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.