BIS(2,2,2-TRICHLORO-1,1-DIMETHYLETHYL) PHOSPHOROCHLORIDATE Chemical Properties

Melting point:

mp 81-82 °C

solubility 

crystallized from pentane

form 

colorless solid

BIS(2,2,2-TRICHLORO-1,1-DIMETHYLETHYL) PHOSPHOROCHLORIDATE Usage And Synthesis

Uses

BIS(2,2,2-TRICHLORO-1,1-DIMETHYLETHYL) PHOSPHOROCHLORIDATE is used as a phosphorylating reagent.

Synthesis

Bis(2,2,2-trichloro-1,1-dimethylethyl) Phosphorochloridate is conveniently prepared by the reaction of 2-trichloromethyl-2-propanol with PCl3 in pyridine solvent to afford bis(2,2,2-trichloro-1,1-dimethylethyl) chlorophosphite (71%). The chlorophosphite is oxidized with (Diacetoxyiodo)benzene to give 65% of the desired phosphorochloridate (eq 1). This overall procedure represents an improved synthesis of the phosphorochloridate when compared to the different methods reported in the literature, which give mixtures of bis(2,2,2-trichloro-1,1-dimethylethyl) chlorophosphite and 2,2,2-trichloro-1,1-dimethylethyl dichlorophosphite.^[1][2]

Synthesis Reference(s)

[1](a) Gerrard, W. JCS 1944, 85. (b) Gerrard, W.; Wyvill, P. L. Research (London) 1949, 2, 536. (c) Gerrard, W.; Isaacs, M. J. D.; Machell, G.; Smith, K. B.; Wyvill, P. L. JCS 1953, 1920. (d) Gerrard, W.; Green, W. J.; Phillips, R. J. JCS 1954, 1148.
[2] (a) Abramov, V. S.; Khairullin, V. K. JGU 1957, 27, 501. (b) Sasse, K. MOC 1964, XII/2, 45.

BIS(2,2,2-TRICHLORO-1,1-DIMETHYLETHYL) PHOSPHOROCHLORIDATE(17677-92-8)Related Product Information

• 1,1,1-TRICHLORO-2-METHYL-2-PROPANOL HEMIHYDRATE
• BIS(2,2,2-TRICHLORO-1,1-DIMETHYLETHYL) PHOSPHOROCHLORIDATE
• di-tert-butylChlorophosphate
• BIS(2-CHLOROETHYL)PHOSPHITE
• DIETHYL CHLOROPHOSPHITE
• Chlorobutanol
• DIMETHYL PHOSPHOROCHLORIDATE
• BIS(2,2,2-TRICHLOROETHYL) PHOSPHOROCHLORIDITE
• Diethyl chlorophosphate
• Diisopropyl chlorophosphate
• Chlorobutanol
• BIS(2,2,2-TRICHLOROETHYL) PHOSPHOROCHLORIDATE