84718-92-3

Basic information

• Product Name: Phosphonamidic acid, P-(1,1-dimethylethyl)-N-phenyl-, methyl ester
• CAS NO: 84718-92-3
• Molecular Formula: C11H18NO2P
• Molecular Weight: 227.243
• Mol File: 84718-92-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Phosphonamidic acid, P-(1,1-dimethylethyl)-N-phenyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonamidic acid, P-(1,1-dimethylethyl)-N-phenyl-, methyl ester(84718-92-3)
• EPA Substance Registry System: Phosphonamidic acid, P-(1,1-dimethylethyl)-N-phenyl-, methyl ester(84718-92-3)

Safety Data

• Hazardous Substances Data: 84718-92-3(Hazardous Substances Data)

Upstream product

• 97730-03-5 methyl tert-butylimidazolidophosphonate 
• 84674-98-6 methanesulfonic O-methyl-tert-butylphosphonic anhydride 
• 34250-35-6 methyl tert-butylphosphonochloridate 
• 97730-01-3 O-methyl-tert-butylphosphonic trifluoromethanesulfonic anhydride 
• 62-53-3 aniline 
• 67-56-1 methanol 
• 84718-90-1 t-butyl(phenyl)phosphinic azide 

Relevant articles and documents

Anhydrides of Phosphorus and Sulfur Acids, 2. Mixed Anhydrides of Phosphoric, Phosphonic, and Phosphinic Acids with Sulfonic Acids and Sulfuric Monoimidazolide. New Methods of Synthesis, Novel Structures, Phosphorylating Properties

New applications of methods leading to anhydrides RR'P(O)OSO2R'' (1) are described: a) Reaction of acids RR'P(O)OH (2) with sulfonic imidazolides. b) Reaction of phosphorus imidazolides 4 with sulfonic acids and sulfonic anhydrides.New methods of synthesis of anhydrides 1 have been developed. c) Reaction of phosphorus acid silyl esters RR'P(O)OSiMe3 (9) with methanesulfonic and trifluoromethanesulfonic anhydrides. d) Reaction of bis(trimethylsilyl) tert-butylphosphonate (10) with methanesulfonic acid leading to tBuP(O)(OSO2Me)2 (11). e) Reaction of stannyl phosphate (EtO)2P(O)OSnMe3 (15) with methanesulfonic anhydride. f) Reaction of phosphorus acid silyl esters 9 with trimethylsilyl trifluoromethanesulfonate.All methods result in high yields and can be adapted to a variety of anhydrides 1 derived from phosphoric, phosphonic, and phosphinic acids on the one hand and methanesulfonic, trifluoromethanesulfonic acids and sulfuric monoimidazolide on the other.Phosphonium intermediates have been demonstrated by low temperature FT 31P NMR spectroscopy for reaction b) and c).The anhydrides 1 are readily converted into imidazolides 4 by the reaction with N-(trimethylsilyl)imidazole which proceeds via two distinct phosphonium intermediates.With neutral and weakly basic nucleophiles, the anhydrides 1 behave as phosphorylating agents.

PHOTOLYSIS OF SOME UNSYMMETRICAL PHOSPHINIC AZIDES IN METHANOL. RELATIVE MIGRATORY APTITUDES OF ALKYL GROUPS AND PHENYL IN THE CURTIUS-LIKE REARRANGEMENT.

When an alkylphenylphosphinic azide RPhP(O)N3 (R=Me, Et, Pri or But) is photolysed in MeOH either the alkyl or phenyl group can migrate from P to N in the Curtius-like rearrangement.The composition of the product shows that migration of the alkyl group R is preferred.However, the preference is not great and decreases as R changes But->Pri->Et->Me-> (approx. migratory aptitudes relative to Ph: 2.1, 1.7, 1.3, 1.2 respectively), probably because the Ph-P bond is better able to assume the correct conformation for Ph migration when R is less bulky.For t-butylmethylphosphinic azide there is very little preference for migration of But relative to Me.Small amounts of unrearranged products such as ButPhP(O)NHOMe and ButPhP(O)NH2 are generally produced in the photolyses, together with the methyl phosphinates RPhP(O)OMe (major product when R=Me) resulting from (non-photochemical) solvolysis of the azide.