5689-75-8

Basic information

• Product Name: Oxiranemethanamine
• Synonyms: Epihydrinamine;Oxiranemethanamine
• CAS NO: 5689-75-8
• Molecular Formula: C₃H₇NO
• Molecular Weight: 73.09
• Mol File: 5689-75-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 105.0±13.0 °C(Predicted)
• Appearance: /
• Density: 1.058±0.06 g/cm3(Predicted)
• PKA: 9.61±0.29(Predicted)
• CAS DataBase Reference: Oxiranemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranemethanamine(5689-75-8)
• EPA Substance Registry System: Oxiranemethanamine(5689-75-8)

Safety Data

• Hazardous Substances Data: 5689-75-8(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 96-23-1 1,3-Dichloro-2-propanol 
• 7664-41-7 ammonia 
• 616-30-8 3-Amino-1,2-propanediol 

Downstream Products

• 57726-19-9 1-[4-(3-Amino-2-hydroxy-propoxy)-phenyl]-3-cyclohexyl-urea 
• 107-11-9 1-amino-2-propene 
• 2186-25-6 m-tolyl glycidyl ether 

Relevant articles and documents

Epoxidation of Primary and Secondary Alkenylammonium Salts with Dimethyldioxirane, Methyl(trifluoromethyl)dioxirane, and m-Chloroperbenzoic Acid. A General Synthetic Route to Epoxyalkylamines

Selective syn-epoxidation of C=C double bonds in primary and secondary alkenylammonium arenesulfonate salts 3H(+), to give the corresponding epoxyalkylammonium salts 4H(+), has been achieved by reaction with electrophilic O-transfer reagents such as m-CPBA, methyl(trifluoromethyl)dioxirane (TFDO), and dimethyldioxirane (DMDO).Epoxyalkylamines 4 are easily obtained in high yields from the corresponding epoxyalkylammonium salts 4H(+) by simple deprotonation with sodium carbonate.The ammonium group deactivates the C=C double bond, and hence the epoxidation rate is slower than in the case of simple olefins.H-Bonding interaction between the ammonium group and the O-transfer reagent (m-CPBA and DMDO) in the transition state is claimed to account for the rate enhancement and diastereoselectivity observed when the necessary conformational requirements are established.The allylic ammonium group is shown to be very efficient in directing the epoxidation with m-CPBA and DMDO on the syn-diastereoface.