103596-43-6

Basic information

• Product Name: 4-fluorodeprenyl
• Synonyms: 4-fluorodeprenyl;2-(4-Fluorophenyl)-1,N-dimethyl-N-(2-propynyl)ethanamine;4-Fluoro-α,N-dimethyl-N-(2-propynyl)benzeneethanamine;p-Fluorodeprenyl
• CAS NO: 103596-43-6
• Molecular Formula: C₁₃H₁₆FN
• Molecular Weight: 205.2712432
• Mol File: 103596-43-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 276.2°C at 760 mmHg
• Flash Point: 120.9°C
• Appearance: /
• Density: 1.024g/cm³
• Vapor Pressure: 0.00486mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: 4-fluorodeprenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4-fluorodeprenyl(103596-43-6)
• EPA Substance Registry System: 4-fluorodeprenyl(103596-43-6)

Safety Data

• Hazardous Substances Data: 103596-43-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H16FN/c1-4-9-15(3)11(2)10-12-5-7-13(14)8-6-12/h1,5-8,11H,9-10H2,2-3H3

Upstream product

• 50-00-0 formaldehyd 
• 103596-36-7 (R,S)-(+/-)-α-methyl-β-(4-fluorophenyl)-N-propynylethylamine 
• 459-02-9 4-fluoroamphetamine 
• 134538-46-8 1-(4-fluorophenyl)-2-nitropropene 
• 459-57-4 4-fluorobenzaldehyde 

Relevant articles and documents

Synthesis of (R)-(-)- and (S)-(+)-4-fluorodeprenyl and (R)-(-)- and (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl and positron emission tomography studies in baboon brain

(R)-(-)- and (S)-(+)-α-methyl-β-4-(fluorophenyl)-N-methyl-N-propynylethylamine ((R)-(-)- and (S)-(+)-4-fluorodeprenyl) were synthesized via the reaction of 4-fluorobenzaldehyde with nitroethane followed by reduction with lithium aluminum hydride to produce racemic 4-fluoroamphetamine, which was resolved by recrystallization with L- or D-N-acetylleucine to yield (R)-(-)-4-fluoroamphetamine or (S)-(+)-4-fluoroamphetamine in >96% enantiomeric excesses and in yields of 42 and 39%, respectively. Alkylation with propargyl bromide gave (R)-(-)- or (S)-(+)-4-fluoronordeprenyl which was reductively methylated (Borch conditions) to produce (R)-(-)- or (S)-(+)-4-fluorodeprenyl. Alkylation of (R)-(-)- or (S)-(+)-4-fluoronordeprenyl with carbon-11 labeled methyl iodide gave (R)-(-)- or (S)-(+)-[N-11C-methyl]-4-fluorodeprenyl in a radiochemical yield of 30-40%. Comparative PET studies of the two labeled enantiomers in baboons showed a significantly lower retention of radioactivity in the striatum for the (S)-(+) enantiomer relative to the (R)-(-) enantiomer.