Bis-(2-chloroethyl)phosphoramidic Dichloride

Abstract

[127-88-8] C4H8Cl4NOP (MW 258.90) InChI = 1S/C4H8Cl4NOP/c5-1-3-9(4-2-6)11(7,8)10/h1-4H2 InChIKey = IQPMYTNILJQKBS-UHFFFAOYSA-N (reagent used in condensation reactions to form cyclophosphamide derivatives, bis(2-arylaminoethyl)amines, and various p-sugars) Alternate Name: (N,N-di-2-chloroethyl) phosphoramidic dichloride; bis(2-chloroethyl)aminophosphoric dichloride; bis(2- chloroethyl)aminophosphoryl dichloride; bis(2-chloroethyl) phosphoramidic dichloride; N,N-bis(2-chloroethyl)phosph- amide dichloride; N,N-bis(2-chloroethyl)phosphoramidic dichloride. Physical Data: mp 53–57 °C; bp 110–114 °C/0.1 MM. Preparative Methods: can be prepared by heating bis-(β-chloroethyl)amine hydrochloride at reflux with excess phosphorus oxychloride and triethylamine. Purification: by distillation, and can be crystallized from acetone– petroleum ether. Handling, Storage, and Precautions: moist white crystals, air sensitive, corrosive, possible carcinogen, highly toxic, possible mutagen. Reacts violently with air, and should be handled and stored under nitrogen. Should be stored in a tightly sealed container in cool dry areas. Use in a fume hood and wear protective gloves, goggles, and clothing. May be fatal if inhaled, swallowed, or absorbed through skin. Irritant to upper respiratory tract, eyes, and skin.