62779-70-8

Basic information

• Product Name: (S)-1-Phenylethane-1,2-diamine
• Synonyms: (S)-1-Phenylethane-1,2-diamine;[S,(+)]-1-Phenylethylenediamine;(1S)-1-Phenyl-1,2-ethanediamine;(S)-1-Phenyl-1,2-ethylenediamine
• CAS NO: 62779-70-8
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19428
• Mol File: 62779-70-8.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-Phenylethane-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-Phenylethane-1,2-diamine(62779-70-8)
• EPA Substance Registry System: (S)-1-Phenylethane-1,2-diamine(62779-70-8)

Safety Data

• Hazardous Substances Data: 62779-70-8(Hazardous Substances Data)

Usage

General Description

(S)-1-Phenylethane-1,2-diamine, also known as L-phenylethylendiamine, is an organic compound that belongs to the class of aromatic amines. It is a chiral molecule with two stereoisomers, (R)-1-Phenylethane-1,2-diamine and (S)-1-Phenylethane-1,2-diamine, with the latter being the enantiomer. (S)-1-Phenylethane-1,2-diamine is commonly used in the pharmaceutical industry as a chiral building block for the synthesis of various pharmaceutical drugs. It has also been studied for its potential application as a chiral ligand in asymmetric synthesis. Additionally, (S)-1-Phenylethane-1,2-diamine has been investigated for its role as a chiral auxiliary in stereoselective reactions, making it a valuable compound in organic chemistry.

Upstream product

• 4103-60-0 2-(2-aminophenyl)acetamide 
• 100-52-7 benzaldehyde 
• 137102-30-8 (S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine 
• 6485-52-5 L-phenylglycine amide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 150884-50-7 benzaldehyde N-boc imine 
• 70-11-1 α-bromoacetophenone 
• 4589-97-3 phenylglyoxime 
• 53641-61-5 1-phenyl-1-acetylamino-2-acetylaminoethane 
• 134625-72-2 (R)-2-azido-1-phenylethanol 
• 56751-12-3 2-chloro-1-phenylethanol 
• 20780-53-4 (R)-Styrene oxide 
• 190393-63-6 (S)-N-(benzyloxycarbonyl)-α-phenylglycinol mesyl ether 

Downstream Products

• 190393-69-2 (S)-N-(benzyloxycarbonyl)-4-phenyl-Δ²-imidazoline 
• 14769-73-4 Levamisole 
• 185137-29-5 (4S)-4-phenyl-1,3-thiazolidine-2-thione 

Relevant articles and documents

Novel α-amino acid-derived phase-transfer catalyst application to a highly enantio- and diastereoselective nitro-Mannich reaction

New quaternary ammonium types of bifunctional asymmetric phase-transfer catalysts bearing multiple hydrogen-bonding donors derived from α-amino acids were readily prepared and found to be highly efficient in the asymmetric nitro-Mannich reactions of amidosulfones. Very broad substrate generality was observed, and the products were achieved in high enantio-/diastereoselectivities (90->99.9% ee, 90:10 to 92:8 dr). Compared with previous reports, the enantioselectivity of aliphatic amidosulfones has been improved to a high level (91-93% ee).

Enantioselective aza-Henry reaction for the synthesis of (S)-levamisole using efficient recyclable chiral Cu(II)-amino alcohol derived complexes

Chiral Cu(II) complexes were generated in situ by the interaction of aminoalcohol based ligands L1-L6 derived from (1R,2S)-(-)-2-aminodiphenylethanol, (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol, (R or S)-valinol and (S)-2-amino-1,1-diphenylpropan-1-ol with 4-tert-butyl-2,6-diformylphenol and screened for aza-Henry reaction of a variety of aromatic, aliphatic N-tosylaldimine and aromatic N-benzenesulfonamide aldimine in toluene at RT. Excellent enantioselectivity, diastereoselectivity (99%) of β-nitro-N-tosylaldamine with good yield (80%) was achieved in case of complex L2-Cu(II) with low catalyst loading. The enantio-pure aza-Henry product obtained was straightforwardly transformed into the enantioenriched chiral vicinal diamine (ee; 96%) with good yield in successive two steps and was further used for the synthesis of (S)-levamisole (an anthelminthic agent). The catalytic system worked well up to five cycles with retention of enantioselectivity.

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.