3012. Dibenzyl Chlorophosphonate

Nomenclature

CAS number: 538-37-4
Phosphorochloridic acid bisphenylmethyl ester; benzyl phosphorochloridate; dibenzylchlorophosphate; DBPCl; dibenzylphosphoryl chloride.
C14H14ClO3P; mol wt 296.69.
C 56.68%, H 4.76%, Cl 11.95%, O 16.18%, P 10.44%.

Description and references

Prepd by adding sulfuryl chloride to dibenzyl phosphite at 17-19° in CCl4 diluent: Atherton et al., J. Chem. Soc. 1948, 1106; by adding chlorine to dibenzyl phosphite in CCl4 at below 0°: Atherton et al., US 2490573 (1949 to Hoffmann-La Roche).

Chemical structure

Properties

Thick oil, dec on standing or distillation. Identified by its reaction with ammonia or amines to form corresponding dibenzyl aminophosphonates.

Use

In solns with inert solvents such as chloroform, carbon tetrachloride, benzene and ether for the phosphorylation of nucleosides and amino acids.