23587-60-2

Basic information

• Product Name: Methanamine, 1,1-bis(diphenylphosphinyl)-N,N-dimethyl-
• CAS NO: 23587-60-2
• Molecular Formula: C27H27NO2P2
• Molecular Weight: 459.464
• Mol File: 23587-60-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Methanamine, 1,1-bis(diphenylphosphinyl)-N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanamine, 1,1-bis(diphenylphosphinyl)-N,N-dimethyl-(23587-60-2)
• EPA Substance Registry System: Methanamine, 1,1-bis(diphenylphosphinyl)-N,N-dimethyl-(23587-60-2)

Safety Data

• Hazardous Substances Data: 23587-60-2(Hazardous Substances Data)

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 25419-99-2 (dimethylamino)(diphenylphosphinoyl)methoxymethane 
• 1352709-73-9 (diphenylphosphoryl)(N,N-dimethylamino)chloromethane 
• 4559-70-0 Diphenylphosphine oxide 
• 14642-79-6 benzyloxy-trimethylsilane 

Relevant articles and documents

Ambident reactivity of chloro(dialkylamino)-(diphenylphosphinoyl)methanes

The chemical properties of chloro(dialkylamino)(diphenylphosphinoyl) methanes have been studied using the simplest compound of this series, chloro(dimethylamino)(diphenylphosphinoyl)methane, as an example. Chloro- (dimethylamino)(diphenylphosphinoyl)methane shows ambident reactivity when reacting with electrophiles and nucleophiles depending on coreactant nature, it behaves as either electrophilic substrate or phosphorus nucleophile. This fact can be explained by its dissociation in solutions with both C-Cl bond cleavage to give (dimethylamino)- (diphenylphosphinoyl)methyl cation and Cl- anion and C-P bond cleavage to form chloro(dimethylamino)methyl cation and diphenylphosphinite anion. The capability of chloro(dimethylamino) (diphenylphosphinoyl)methane to produce spontaneously Ph2PO-anion allows us to recommend application in organic and organophosphorus synthesis as a synthetic equivalent (synthon) of diphenylphosphinite anion.

Synthesis of polyfunctionalized methylphosphine oxides

N,N-Dialkylamino(diphenylphosphoryl)chloromethanes, a new type of organophosphorus compounds, were synthesized. On dissolving in polar and low polar solvents, N,N-dialkylamino(diphenylphosphoryl)chloromethanes dissociate spontaneously with the P - C bond cleavage to form the diphenylphosphinite anion Ph2PO-. This was confirmed by the reaction of N,N-dimethylamino(diphenylphosphoryl)chloromethane with electrophilic substrates to form the corresponding addition or substitution products of Ph 2PO-. The capability of spontaneous generating the diphenylphosphinite anion considers accessible N,N- dimethylamino(diphenylphosphoryl)chloromethane as a synthetic equivalent of the diphenylphosphinite anion.