128541-09-3

Basic information

• Product Name: Propanedioic acid, diazo-, 1,1-dimethylethyl 2-propenyl ester
• CAS NO: 128541-09-3
• Molecular Formula: C10H14N2O4
• Molecular Weight: 226.232
• Mol File: 128541-09-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, diazo-, 1,1-dimethylethyl 2-propenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, diazo-, 1,1-dimethylethyl 2-propenyl ester(128541-09-3)
• EPA Substance Registry System: Propanedioic acid, diazo-, 1,1-dimethylethyl 2-propenyl ester(128541-09-3)

Safety Data

• Hazardous Substances Data: 128541-09-3(Hazardous Substances Data)

Upstream product

• 40052-13-9 mono-tert-butyl malonate 

Downstream Products

• 127181-31-1 (1RS,2SR)-1-amino-2-(hydroxymethyl)cyclopropanecarboxylic acid 
• 112575-35-6 (E)-1-Amino-2-(hydroxymethyl)cyclopropane-1-carboxylic acid 

Relevant articles and documents

Intramolecular Cyclopropanation: Stereospecific Synthesis of (E)- and (Z)-1-Aminocyclopropane-1-carboxylic Acids

tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields.The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclohexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 15 via Curtius- or Hoffmann-type rearrangements, respectively.The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40percent overall from malonic acid).The free amino acids 12 and 13 can be liberated in two steps.