675622-46-5

Basic information

• Product Name: Phosphonic diamide, N-methyl-N'-phenyl-P-(1-phenylethyl)-
• CAS NO: 675622-46-5
• Molecular Formula: C15H19N2OP
• Molecular Weight: 274.302
• Mol File: 675622-46-5.mol

Chemical Properties

• CAS DataBase Reference: Phosphonic diamide, N-methyl-N'-phenyl-P-(1-phenylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic diamide, N-methyl-N'-phenyl-P-(1-phenylethyl)-(675622-46-5)
• EPA Substance Registry System: Phosphonic diamide, N-methyl-N'-phenyl-P-(1-phenylethyl)-(675622-46-5)

Safety Data

• Hazardous Substances Data: 675622-46-5(Hazardous Substances Data)

Upstream product

• 188540-15-0 N-hydroxylamine 
• 74-89-5 methylamine 
• 675622-48-7 O-benzylsulfonyl-N-[phenyl(1-phenylethyl)phosphinoyl]hydroxylamine 
• 140458-27-1 N-<α-methylbenzyl(phenyl)phosphinoyl>-O-methylsulfonylhydroxylamine 

Relevant articles and documents

Competing sulfonylation and phosphonylation following rearrangement of an O-sulfonyl-N-phosphinoylhydroxylamine with tert-butylamine: Demonstration of a phosphonamidic-sulfonic anhydride intermediate and 18O-labelling evidence on how it may be formed

Reaction of R(Ph)P(O)NHOSO2Bn (R = PhMeCH) with Bu tNH2 in CH2Cl2 gives a mixture of RP(O)(NHPh)NHBut and ButNHSO2Bn, the proportion of the sulfonamide increasing steadily (14.6% to 32.9%) as the concentration of amine is reduced (8.0 to 0.2 mol dm-3). Apparently the phenyl and sulfonate groups in the substrate become transposed, giving a phosphonamidic-sulfonic anhydride RP(O)(NHPh)OSO2Bn which then reacts at the phosphorus or sulfur atom to give the final products; an authentic sample of the anhydride gives similar mixtures of products. Substrate labelled with 18O in the sulfonyl position (57 mol% one 18O atom) gives sulfonamide containing most but not all of the label (43.7 mol% one 18O atom with 2.0 mol dm-3 amine). This implies partial equilibration of the three sulfonate oxygen atoms during rearrangement, or after the anhydride intermediate has been formed.

Lossen-like Rearrangement of N--O-methylsulfonylhydroxylamine with Methylamine: Retention of Configuration at Phosphorus as revealed by X-Ray Crystallography

The diastereoisomers of the title compound 6 rearrange with high stereospecificity on treatment with MeNH2, giving PhMeCHP(O)(NHMe)NHPh in which the migrating phenyl group has been replaced by MeNH2 with retention of configuration at phosphorus.