937-52-0

Basic information

• Product Name: (R)-(-)-1-Methyl-3-phenylpropylamine
• Synonyms: R-MPA;(R)-(-)-1-METHYL-3-PHENYLPROPYLAMINE;(R)-1-METHYL-3-PHENYL-PROPYLAMINE;(R)-2-AMINO-4-PHENYLBUTANE;(2R)-2-Amino-4-phenylbutane;(R)-a-Methylbenzenepropanamine;(R)-1-Methyl-3-phenyl-1-propanamine;(R)-4-Phenylbutane-2-amine
• CAS NO: 937-52-0
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• Mol File: 937-52-0.mol
• Article Data: 70

Chemical Properties

• Melting Point: 143°C (estimate)
• Boiling Point: 230.33°C (estimate)
• Flash Point: 97.778 °C
• Appearance: Clear colorless/Liquid
• Density: 0.936
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: 1.513-1.515
• Storage Temp.: 0-6°C
• PKA: 10?+-.0.35(Predicted)
• CAS DataBase Reference: (R)-(-)-1-Methyl-3-phenylpropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-1-Methyl-3-phenylpropylamine(937-52-0)
• EPA Substance Registry System: (R)-(-)-1-Methyl-3-phenylpropylamine(937-52-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53-34-24/25
• Safety Statements: 37/39-26-61-45-36/37/39
• RIDADR: 2922
• Hazardous Substances Data: 937-52-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

(R)-4-Phenyl-2-butane was used for study of preparation and biological activity of dipeptide nitriles as reversible and potent cathepsin S inhibitors.

InChI:InChI=1/C10H15N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8,11H2,1H3/t9-/m1/s1

Upstream product

• 22374-89-6 (RS)-1-methyl-3-phenylpropylamine 
• 492-41-1 (1R,2S)-norephedrine 
• 71255-70-4 benzylacetone O-methyloxime 
• 137005-77-7 N-((R)-2-methoxy-1-phenylethyl)-1-methyl-3-phenylpropylamine 
• 88976-53-8 *,R^*)>-α-methyl-N-(1-phenylethyl)benzenepropanamide 
• 107300-18-5 (2S,2''R)-1-[N-methoxycarbonyl-N-(1-methyl-3-phenylpropyl)amino]-2-(methoxymethyl)pyrrolidine 
• 202123-10-2 (4-Chloro-benzyl)-[1-methyl-3-phenyl-prop-(E)-ylidene]-amine 
• 199615-24-2 (2R,1'R)-[1'-(1-naphthyl)ethyl]-4-phenyl-2-butylamine 
• 141-78-6 ethyl acetate 
• 104-53-0 3-phenyl-propionaldehyde 
• 254745-24-9 (R)-N-(3-phenylpropylidene)-1-(1-napthyl)ethylamine 
• 107381-30-6 hydrocinnamaldehyde SAMP-hydrazone 
• 2550-26-7 4-Phenyl-2-butanone 
• 129757-52-4 (R)-N-(methoxycarbonyl)-2-amino-4-phenylbutane 

Downstream Products

• 97948-60-2 (2R,3S,4R,5R)-2-Hydroxymethyl-5-[6-((R)-1-methyl-3-phenyl-propylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol 
• 137029-98-2 (R)-N-(p-toluenesulfonyl)-1-methyl-3-phenylpropylamine 
• 153357-82-5 (R)-N,N-di-(p-toluenesulfonyl)-1-methyl-3-phenylpropylamine 
• 2344-70-9 1-phenyl-3-butanol 
• 4187-57-9 (S)-1-methyl-3-phenylpropylamine 
• 116199-45-2 (S)-1-methyl-3-phenylpropyl azide 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 75659-06-2 (+)-(R)-α-methyl-N-(phenylmethyl)benzenepropanamine 
• 83167-32-2 (S,R)-labetalol 
• 75659-07-3 (R,R)-labetalol 

Relevant articles and documents

Stereo-Divergent Enzyme Cascades to Convert Racemic 4-Phenyl-2-Butanol into either (S)- or (R)-Corresponding Chiral Amine

The synthesis of enantiopure chiral amines from racemic alcohols is a key transformation in the chemical industry, e. g., in the production of active pharmaceutical ingredients (APIs). However, this reaction remains challenging. In this work, we propose a one-pot enzymatic cascade for the direct conversion of a racemic alcohol into either (S)- or (R)-enantiomers of the corresponding amine, with in-situ cofactor recycling. This enzymatic cascade consists of two enantio-complementary alcohol dehydrogenases, both NADH and NADPH oxidase for in-situ recycling of NAD(P)+ cofactors, and either (S)- or (R)-enantioselective transaminase. This cell-free biocatalytic system has been successfully applied to the conversion of racemic 4-phenyl-2-butanol into the high value (S)- or (R)-enantiomers of the amine reaching good (73 % (S)) and excellent (>99 % (R)) enantioselectivities.

Iterative Alanine Scanning Mutagenesis Confers Aromatic Ketone Specificity and Activity of L-Amine Dehydrogenases

Direct reductive amination of prochiral ketones catalyzed by amine dehydrogenases is attractive in the synthesis of active pharmaceutical ingredients. Here, we report the protein engineering of L-Bacillus cereus amine dehydrogenase to allow reactivity on synthetically useful aromatic ketone substrates using an iterative, multiple-site alanine scanning mutagenesis approach. Mutagenesis libraries based on molecular docking, iterative alanine scanning, and double-proximity filter approach significantly expand the scope of active pharmaceutical ingredients relevant building blocks. The eventual quintuple mutant (A115G/T136A/L42A/V296A/V293A) showed reactivity toward aromatic ketones 12 a (5-phenyl-pentan-2-one) and 13 a (6-phenyl-hexan-2-one), which have not been reported to serve as targets of reductive amination by currently available amine dehydrogenases. Docking simulation and tunnel analysis provided valuable insights into the source of the acquired specificity and activity.

Development of a: Corynebacterium glutamicum bio-factory for self-sufficient transaminase reactions

The development of biocatalytic routes for the synthesis of chiral amines starting from achiral building blocks is highly desirable. Here, we report a self-sufficient whole-cell system for the conversion of a model ketone to the corresponding cyclic imine, in good isolated yield (42%) and excellent enantioselectivity (>99% ee). The Corynebacterium glutamicum host produces the transaminase biocatalyst, cofactor and 'smart' amine donor (cadaverine or putrescine) in vivo, and highlights the potential for producing high-value chemicals from readily available building blocks. The report represents the first example of the application of a metabolically engineered organism for the production of smart diamine donors and their application in a transaminase biotransformation.