3082-64-2

Basic information

• Product Name: (R)-(+)-1-Phenylpropylamine
• Synonyms: (R)-(+)-PHENYLPROPYLAMINE;(R)-(+)-ETHYLBENZYLAMINE;(R)-1-PHENYLPROPAN-1-AMINE;(R)-(+)-1-PHENYLPROPYLAMINE;(R)-1-PHENYLPROPYLAMINE;R(+)-A-ETHYLBENZYLAMINE;(R)-(+)-ALPHA-ETHYLBENZYLAMINE;(R)-ALPHA-ETHYLBENZYLAMINE
• CAS NO: 3082-64-2
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• EINECS: -0
• Product Categories: chiral;Chiral Reagent;Chiral Compound;Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 3082-64-2.mol
• Article Data: 69

Chemical Properties

• Melting Point: -69°C
• Boiling Point: 205°C
• Flash Point: 77°C
• Appearance: /
• Density: 0.940 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.272mmHg at 25°C
• Refractive Index: n20/D 1.520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, Ethyl Acetate
• PKA: 9.34±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 3029904
• CAS DataBase Reference: (R)-(+)-1-Phenylpropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-Phenylpropylamine(3082-64-2)
• EPA Substance Registry System: (R)-(+)-1-Phenylpropylamine(3082-64-2)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45-39-37-36
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3082-64-2(Hazardous Substances Data)

Usage

Description

(R)-(+)-1-Phenylpropylamine is a chiral phenylalkylamine derivative, characterized by its clear, colorless oil appearance. It is an optically active compound, which means it can be distinguished by its interaction with plane-polarized light. This unique property makes it a valuable component in various applications across different industries.

Uses

Used in Pharmaceutical Industry:
(R)-(+)-1-Phenylpropylamine is used as a key intermediate for the synthesis of optically active products. Its chiral nature allows for the creation of enantiomers, which are crucial in the development of drugs with specific therapeutic effects and reduced side effects. The ability to produce optically active compounds is essential in the pharmaceutical industry, as it enables the development of more effective and safer medications.
Used in Research and Development:
(R)-(+)-1-Phenylpropylamine is used as a research compound for studying metabolic Cytochrome P-455 nm complex formation. Cytochrome P450 (CYP450) is a group of enzymes that play a vital role in the metabolism of drugs and other substances in the body. Understanding the interaction between (R)-(+)-1-Phenylpropylamine and these enzymes can provide valuable insights into drug metabolism, leading to the development of more effective and safer pharmaceuticals.
Used in Chemical Synthesis:
(R)-(+)-1-Phenylpropylamine is also used as a building block in the synthesis of various organic compounds. Its unique structure and optical activity make it a valuable component in the creation of complex molecules with specific properties and applications. This versatility allows it to be utilized in a wide range of chemical processes and industries, from pharmaceuticals to materials science.

InChI:InChI=1/C9H13N/c1-2-9(10)8-6-4-3-5-7-8/h3-7,9H,2,10H2,1H3/t9-/m0/s1

Upstream product

• 2941-20-0 1-phenylpropylamine 
• 2114-36-5 (S)-1-bromo-1-phenyl-propane 
• 31053-44-8 Propiophenonbenzoylhydrazon 
• 2157-50-8 propiophenone oxime 
• 125402-82-6 1-phenylpropan-1-one O-(phenylmethyl)oxime 
• 54542-07-3 1-phenyl-propan-1-one-O-methyl-oxime 
• 131214-09-0 (2R,1'R)-2-<(1'-phenylpropyl)amino>-2-phenylethanol 
• 121328-37-8 (S)-4-Isopropyl-3-((R)-1-phenyl-propyl)-oxazolidin-2-one 
• 75039-34-8 (E)-propiophenone O-methyl oxime 
• 125402-82-6 (E)-1-phenylpropanone O-benzyl oxime 
• 177265-21-3 2,2-Dimethyl-N-{(R)-1-[2-((R)-(R)-1-phenyl-propylsulfinamoyl)-phenyl]-ethyl}-propionamide 
• 873-66-5 1-propenylbenzene 
• 154675-31-7 N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide 
• 439271-80-4 (R)-N-(1-phenylpropyl)formamide 

Downstream Products

• 69622-08-8 (R)-N-(p-Aminophenylacetyl)-1-phenyl-n-propylamin 
• 92455-88-4 2-Acetylamino-N-((R)-1-phenyl-propyl)-acrylamide 
• 127106-87-0 [2-Phenyl-eth-(E)-ylidene]-((R)-1-phenyl-propyl)-amine 
• 37696-15-4 Eth-(E)-ylidene-((R)-1-phenyl-propyl)-amine 
• 37696-19-8 ((R)-1-Phenyl-propyl)-prop-(E)-ylidene-amine 
• 37696-23-4 [2-Methyl-prop-(E)-ylidene]-((R)-1-phenyl-propyl)-amine 
• 128257-18-1 (R)-N-Methyl-1-phenylpropylamine 
• 164033-11-8 (R)-(+)-1-phenylpropyl isocyanate 
• 1027169-52-3 (S)-2-[(S)-2-(3,3-Dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N¹-[2-hydroxy-1-methyl-2-((R)-1-phenyl-propylcarbamoyl)-ethyl]-N⁴,N⁴-dimethyl-succinamide 
• 214214-53-6 2-[1-(dimethylamino)propyl]benzene 
• 174635-69-9 (+)-SB 222201 
• 174636-33-0 (S)-(-)-N-(α-ethylbenzyl)-3-hydroxy-2-phenyl-4-quinoline carboxamide 
• 218167-54-5 (R)-3-[(S)-2,2-Dimethyl-1-((R)-1-phenyl-propylcarbamoyl)-propylcarbamoyl]-6-phenyl-hexanoic acid tert-butyl ester 

Relevant articles and documents

Combined Theoretical and Experimental Studies Unravel Multiple Pathways to Convergent Asymmetric Hydrogenation of Enamides

We present a highly efficient convergent asymmetric hydrogenation of E/Z mixtures of enamides catalyzed by N,P-iridium complexes supported by mechanistic studies. It was found that reduction of the olefinic isomers (E and Z geometries) produces chiral amides with the same absolute configuration (enantioconvergent hydrogenation). This allowed the hydrogenation of a wide range of E/Z mixtures of trisubstituted enamides with excellent enantioselectivity (up to 99% ee). A detailed mechanistic study using deuterium labeling and kinetic experiments revealed two different pathways for the observed enantioconvergence. For α-aryl enamides, fast isomerization of the double bond takes place, and the overall process results in kinetic resolution of the two isomers. For α-alkyl enamides, no double bond isomerization is detected, and competition experiments suggested that substrate chelation is responsible for the enantioconvergent stereochemical outcome. DFT calculations were performed to predict the correct absolute configuration of the products and strengthen the proposed mechanism of the iridium-catalyzed isomerization pathway.

Simultaneous Preparation of (S)-2-Aminobutane and d -Alanine or d -Homoalanine via Biocatalytic Transamination at High Substrate Concentration

(S)-2-Aminobutane, d-alanine, and d-homoalanine are important intermediates for the production of various active pharmaceutical ingredients and food additives. The preparation of these small chiral amine or amino acids with high water solubility still demands searching for efficient methods. In this work, we identified an ω-transaminase (ω-TA) from Sinirhodobacter hungdaonensis (ShdTA) that catalyzed the kinetic resolution of racemic 2-aminobutane at a concentration of 800 mM using pyruvate as the amino acceptor, leading to the simultaneous isolation of enantiopure (S)-2-aminobutane and d-alanine in 46% and 90% yield, respectively. In addition, (S)-2-aminobutane (98% ee) and d-homoalanine (99% ee) were isolated in 45% and 93% yield, respectively, in the kinetic resolution of racemic 2-aminobutane at a concentration of 400 mM coupled with deamination of l-threonine by threonine deaminase. We thus developed a biocatalytic process for the practical synthesis of these valuable small chiral amine and d-amino acids.

Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases

Chiral primary amines are important intermediates in the synthesis of pharmaceutical compounds. Fungal reductive aminases (RedAms) are NADPH-dependent dehydrogenases that catalyse reductive amination of a range of ketones with short-chain primary amines supplied in an equimolar ratio to give corresponding secondary amines. Herein we describe structural and biochemical characterisation as well as synthetic applications of two RedAms fromNeosartoryaspp. (NfRedAm andNfisRedAm) that display a distinctive activity amongst fungal RedAms, namely a superior ability to use ammonia as the amine partner. Using these enzymes, we demonstrate the synthesis of a broad range of primary amines, with conversions up to >97% and excellent enantiomeric excess. Temperature dependent studies showed that these homologues also possess greater thermal stability compared to other enzymes within this family. Their synthetic applicability is further demonstrated by the production of several primary and secondary amines with turnover numbers (TN) up to 14 000 as well as continous flow reactions, obtaining chiral amines such as (R)-2-aminohexane in space time yields up to 8.1 g L?1h?1. The remarkable features ofNfRedAmand NfisRedAm highlight their potential for wider synthetic application as well as expanding the biocatalytic toolbox available for chiral amine synthesis.