ORGANIC PHOSPHORUS-COMPOUNDS .71. PREPARATION, PROPERTIES, AND STRUCTURE OF BIS(AMINOMETHYL)PHOSPHINIC ACID, (H2NCH2)2P(O)OH

Bis(aminomethyl)phosphinic acid, (H2NCH2)2P(O)OH · HCl, was prepared by debenzylation of (C6H5CH2NHCH2)2P(O)OH · HCl with hydrogen using 5% Pd on C as catalyst, and from bis(t-butylaminomethyl)phosphinic acid, (t-C4H9NHCH2)2P(O)OH, by isobutylene elimination in concentrated aqueous hydrobromic acid at 175°C in sealed tube. Interaction of bis(chloromethyl)phosphinic acid with ammonia in an autoclave produced methylaminomethylphosphinic acid, CH3NHCH2P(O)(OH)2. A mechanism for the formation of this product is proposed. Several derivatives of (H2NCH2)P(O)OH such as (RNHCH2)2P(O)OH, R = C6H5CO, CICH2CO, [H2NHNC(=NH)NHCH2]2P(O)OH and [(CH3)3SiNHCH2]2P(O)OSi(CH3)3 were prepared. © 1979.