623143-32-8

Basic information

• Product Name: (S)-1-P-TOLYLPROPAN-1-AMINE
• Synonyms: (S)-1-P-TOLYLPROPAN-1-AMINE
• CAS NO: 623143-32-8
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• Mol File: 623143-32-8.mol

Chemical Properties

• Boiling Point: 228.3±9.0 °C(Predicted)
• Appearance: /
• Density: 0.935±0.06 g/cm3(Predicted)
• PKA: 9.50±0.10(Predicted)
• CAS DataBase Reference: (S)-1-P-TOLYLPROPAN-1-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-P-TOLYLPROPAN-1-AMINE(623143-32-8)
• EPA Substance Registry System: (S)-1-P-TOLYLPROPAN-1-AMINE(623143-32-8)

Safety Data

• Hazardous Substances Data: 623143-32-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-1-P-TOLYLPROPAN-1-AMINE is used as a key intermediate in the synthesis of various pharmaceuticals, including antidepressants and antipsychotic medications. Its unique structure and properties make it an essential component in the development of these medications, contributing to their efficacy and therapeutic potential.
Used in Organic Compound Production:
(S)-1-P-TOLYLPROPAN-1-AMINE serves as a precursor in the production of other organic compounds, showcasing its versatility and importance in the field of chemistry. Its ability to be incorporated into a wide range of molecules highlights its utility in creating diverse chemical structures for various applications.
Used in Medicinal Chemistry Research:
Due to its various biological activities and unique properties, (S)-1-P-TOLYLPROPAN-1-AMINE is extensively used in medicinal chemistry research. It aids in the exploration of new drug targets, the development of novel therapeutic agents, and the investigation of the underlying mechanisms of various diseases.

Upstream product

• 54582-25-1 1-(p-tolyl)propan-1-one oxime 
• 104-87-0 4-methyl-benzaldehyde 
• 918165-80-7 (S)-4-[1-(4'-methylphenyl)propyl]amino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-one 
• 145425-10-1 N-[1-(4-methylphenyl)propyl]-P,P-diphenylphosphinoylamide 
• 5337-93-9 4'-methylpropiophenone 
• 58824-48-9 1-(4-methylphenyl)-2-propen-1-ol 

Relevant articles and documents

One-Pot Transformation of Ketoximes into Optically Active Alcohols and Amines by Sequential Action of Laccases and Ketoreductases or ω-Transaminases

An enzymatic one-pot process for asymmetric transformation of prochiral ketoximes into alcohols or amines was developed by sequential coupling of a laccase-catalyzed deoximation either with a ketone reduction (ketoreductase, KRED) or bioamination (ω-transaminase, ω-TA) in aqueous medium. An accurate selection of biocatalysts provided the corresponding products in excellent enantiomeric excesses and overall conversions ranging from 83 to >99 % for alcohols and 70 to >99 % for amines. Likewise, the employment of exclusively 1 % (w/w) of Cremophor, a polyethoxylated castor oil, as co-solvent enabled to reach concentrations up to 100 mM in the chiral alcohols cascade.

Chemoenzymatic one-pot synthesis in an aqueous medium: combination of metal-catalysed allylic alcohol isomerisation-asymmetric bioamination

The ruthenium-catalysed isomerisation of allylic alcohols was coupled, for the first time, with asymmetric bioamination in a one-pot process in an aqueous medium. In the cases involving prochiral ketones, the ω-TA exhibited excellent enantioselectivity, identical to that observed in the single step. As a result, amines were obtained from allylic alcohols with high overall yields and excellent enantiomeric excesses.

Efficient dual catalytic enantioselective diethylzinc addition to the exocyclic C{double bond, long}N double bond of some 1,2,4-N-triazinylarylimines using polymer-supported chiral β-amino alcohols derived from norephedrine

Chiral N,N-dialkylnorephedrines and their corresponding copolymers were evaluated as chiral ligands for the enantioselective diethylzinc addition to the exocyclic C{double bond, long}N double bond of some 4-arylideneamino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-ones 2a-f. The use of a dual catalytic system (amino alcohol/halosilane) in the titled asymmetric reaction was examined. The enantioselective ethylation reaction has been successfully carried out in the heterogeneous system even at low temperature. The corresponding 4-(1-arylpropyl)amino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-ones 4a-f were obtained in high yields with high enantioselectivities using chiral polymers (up to 91% ee), which are almost the same as those obtained from homogeneous analogues (up to 92% ee). The diethylzinc reagent neither opened the 1,2,4-triazinyl heterocyclic ring nor attacked the carbonyl or the thione groups of the 1,2,4-triazinyl heterocyclic ring and the addition reaction took place exclusively at the exocyclic electrophilic carbon atom yielding the C-ethylated products 4a-f. Reductive cleavage of the 1,2,4-triazinyl heterocyclic ring led smoothly to the corresponding primary aromatic amines 11a-f without significant loss of enantiomeric purity. A?suggestion about the possible transition state for the addition reaction is also presented.

Enantioselective diethylzinc addition to the exocyclic C{double bond, long}N double bond of some 4-arylideneamino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-one derivatives

4-Arylideneamino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-ones 2a-f have been evaluated as substrates in the enantioselective diethylzinc addition reaction in the presence of (1S,2R)-N-alkyl-N-benzylnorephedrines 3a-d as chiral ligands. The utility of using a dual catalytic system (amino alcohol/halosilane) for the diethylzinc addition reaction has been also examined. The addition products 4-(1-arylpropyl)amino-3-mercapto-6-methyl-4H-1,2,4-triazin-5-ones 4a-f were obtained in high yields and with enantiomeric excesses of up to 92%. The treatment of arylimines 2a-f with a diethylzinc reagent did not affect the hetero-ring opening although the C{double bond, long}N double bond of the lateral chain did undergo an addition reaction to yield the C-ethylated products 4a-f. The reductive cleavage of the 1,2,4-triazinyl heterocyclic ring from addition products 4a-f led smoothly to the corresponding free primary amines 5a-f without a significant loss of enantiomeric purity.

Enantioselective addition of diethylzinc to N-diphenylphosphinoylimines employing N,N-dialkyl-1,2-diphenyl-2-aminoethanols as chiral ligands

By fine-tuning the substituents on the nitrogen of (1S,2R) and (1R,2S)-1,2-diphenyl-2-aminoethanols, a chiral ligand 2b was obtained, which showed excellent enantioselectivity, with up to 94% e.e, for the asymmetric addition of diethylzinc to N-diphenylphosphinoylimines 1. In one example, the optically active amide 3c was converted into a new amine 5 with 98% e.e. by a reaction sequence involving Suzuki coupling and hydrolysis without racemization.