17596-79-1

Basic information

• Product Name: (S)-2-Phenyl-1-propylamine
• Synonyms: (S)-(-)-BETA-METHYLPHENETHYLAMINE;(S)-BETA-METHYLPHENETHYLAMINE;(S)-2-PHENYLPROPYLAMINE;(S)-(-)-2-PHENYL-1-PROPYLAMINE;(S)-2-PHENYL-1-PROPYLAMINE;S(-)-beta-methylphenylethylamine;(S)-(-)-β-Methylphenethylamine;(S)-(-)-Beta-Methlphenethylamine
• CAS NO: 17596-79-1
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• Product Categories: Amines;Chiral Compounds;Aminomethyl's;Phenyls & Phenyl-Het;Amines (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Compound;Phenyls & Phenyl-Het
• Mol File: 17596-79-1.mol
• Article Data: 26

Chemical Properties

• Melting Point: 207 °C(lit.)
• Boiling Point: 208.93°C (estimate)
• Flash Point: 178 °F
• Appearance: /
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.197mmHg at 25°C
• Refractive Index: n20/D 1.525(lit.)
• PKA: 9.92±0.10(Predicted)
• BRN: 3195645
• CAS DataBase Reference: (S)-2-Phenyl-1-propylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Phenyl-1-propylamine(17596-79-1)
• EPA Substance Registry System: (S)-2-Phenyl-1-propylamine(17596-79-1)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-27
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 17596-79-1(Hazardous Substances Data)

Usage

Description

(S)-2-Phenyl-1-propylamine is an organic compound that serves as a crucial building block in the synthesis of various pharmaceutical compounds. It is a chiral amine with a phenyl group and a propyl chain, which contributes to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
(S)-2-Phenyl-1-propylamine is used as a key intermediate in the synthesis of pyrazolyl-containing tricyclic derivatives, which are known for their potential as anticancer agents. These derivatives target specific cellular pathways, exhibiting inhibitory effects on tumor growth and progression.
Used in Enantioselective Synthesis:
In the field of organic chemistry, (S)-2-Phenyl-1-propylamine is utilized as a building block for the enantioselective synthesis of pyrizinostatin. Pyrizinostatin is a pyroglutamyl peptidase inhibitor, which has potential applications in the development of novel therapeutics for various diseases.

InChI:InChI=1/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

Upstream product

• 582-22-9 2-phenylpropylamine 
• 13490-74-9 S(+)-2-phenyl-propanoic acid amide 
• 109757-73-5 1-nitro-2-phenylpropane 
• 25957-50-0 N-acetylamino-3 phenyl-2 propene 
• 89999-52-0 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-(2-phenyl-propyl)-amine 
• 173216-42-7 (S)-1-azido-2-phenylpropane 
• 34713-70-7 2-Phenylpropanal 
• 591-80-0 pent-4-enoic acid 
• 37778-99-7 (S)-2-phenyl-1-propanol 
• 74669-73-1 2-phenylpropyl 4-methylbenzenesulfonate 
• 28144-67-4 2-phenylallylamine 
• 72171-09-6 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[2-phenyl-prop-(E)-ylidene]-amine 
• 100-42-5 styrene 
• 98-83-9 isopropenylbenzene 

Downstream Products

• 4663-89-2 ((S)-2-phenyl-propyl)-carbamic acid-(2-hydroxy-ethyl ester) 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 93-54-9 1-Phenyl-1-propanol 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 1517-68-6 (S)-1-phenylpropan-2-ol 
• 1572-95-8 (R)-1-phenyl-propan-2-ol 
• 97826-55-6 (+)-6-(S-2-phenyl-1-propylamino)-9-(β-D-ribofuranosyl)-9H-purine 
• 97826-54-5 (-)-N⁶-[(R)-phenylisopropyl]adenosine 
• 124580-20-7 2-(S-2-phenylpropylamino)-adenosine 
• 934-53-2 cumenyl chloride 
• 21260-36-6 [S]-(-)-N-methyl-2-phenylpropylamine 
• 149486-09-9 1-((S)-2-Phenyl-propyl)-3-thiazol-2-yl-thiourea 

Relevant articles and documents

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CO2-Assisted asymmetric hydrogenation of prochiral allylamines

A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO2) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop- 2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction.

Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines

The iridium-catalyzed asymmetric hydrogenation of several N-sulfonyl allyl amines is reported. All substrates can be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The commercially available threonine-derived phosphinite (UbaPHOX) iridium complex has been found to be the best catalyst for this catalytic application, affording β-methyl amines with good to excellent ee values (up to 94%). The synthetic potential of this novel methodology was demonstrated by the formal synthesis of Lorcaserin and LY-404187. (Figure presented.).

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.