65620-66-8

Basic information

• Product Name: (2S)-1-(1,3-benzodioxol-5-yl)propan-2-amine
• Synonyms: (S)-a-Methyl-1,3-benzodioxole-5-ethanamine; (S)-a-Methyl-3,4-(methylenedioxy)phenethylamine; (S)-b-3,4-Methylenedioxyamphetamine; 65620-66-8
• CAS NO: 65620-66-8
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.2157
• Mol File: 65620-66-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 281.7°C at 760 mmHg
• Flash Point: 134.9°C
• Density: 1.163g/cm³
• Vapor Pressure: 0.0035mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: (2S)-1-(1,3-benzodioxol-5-yl)propan-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-(1,3-benzodioxol-5-yl)propan-2-amine(65620-66-8)
• EPA Substance Registry System: (2S)-1-(1,3-benzodioxol-5-yl)propan-2-amine(65620-66-8)

Safety Data

• Hazardous Substances Data: 65620-66-8(Hazardous Substances Data)

Upstream product

• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 4676-39-5 1-(1,3-benzodioxol-5-yl)-2-propanone 
• 42542-10-9 (-)-3,4-Methylenedioxymethamphetamine 
• 66142-89-0 (S)-3,4-methylenedioxymethamphetamine 

Downstream Products

• 42542-10-9 (-)-3,4-Methylenedioxymethamphetamine 
• 66142-89-0 (S)-3,4-methylenedioxymethamphetamine 

Relevant articles and documents

Stereoselective Synthesis of 1-Arylpropan-2-amines from Allylbenzenes through a Wacker-Tsuji Oxidation-Biotransamination Sequential Process

Herein, a sequential and selective chemoenzymatic approach is described involving the metal-catalysed Wacker-Tsuji oxidation of allylbenzenes followed by the amine transaminase-catalysed biotransamination of the resulting 1-arylpropan-2-ones. Thus, a series of nine optically active 1-arylpropan-2-amines were obtained with good to very high conversions (74–92%) and excellent selectivities (>99% enantiomeric excess) in aqueous medium. The Wacker-Tsuji reaction has been exhaustively optimised searching for compatible conditions with the biotransamination experiments, using palladium(II) complexes as catalysts and iron(III) salts as terminal oxidants in aqueous media. The compatibility of palladium/iron systems for the chemical oxidation with commercially available and made in house amine transaminases was analysed, finding ideal conditions for the development of a general and stereoselective cascade sequence. Depending on the selectivity displayed by selected amine transaminase, it was possible to produce both 1-arylpropan-2-amines enantiomers under mild reaction conditions, compounds that present therapeutic properties or can be employed as synthetic intermediates of chiral drugs from the amphetamine family. (Figure presented.).