Di-tert-butyl Chloromethyl Phosphate Chemical Properties

Boiling point:

272.9±23.0 °C(Predicted)

Density 

1.115±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Benzene (Slightly), Methanol (Slightly)

form 

clear liquid

color 

Colorless to Light yellow

Stability:

Moisture Sensitive

InChI

InChI=1S/C9H20ClO4P/c1-8(2,3)13-15(11,12-7-10)14-9(4,5)6/h7H2,1-6H3

InChIKey

LNJAJHJFSKUCIR-UHFFFAOYSA-N

SMILES

P(OC(C)(C)C)(OC(C)(C)C)(OCCl)=O

CAS DataBase Reference

229625-50-7

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36/37

HS Code 

29199000

Di-tert-butyl Chloromethyl Phosphate Usage And Synthesis

Description

Di-tert-butyl (chloromethyl) phosphate has become one of the most common reagents to prepare phosphon-oxymethyl pro-drugs, generally by direct alkylation of hydroxyl or amino groups. Its synthesis was first reported in 1999 via a reaction of di-tert-butyl tetramethylammonium phosphate with chloroiodomethane. This approach required the use of the corresponding tetramethylammonium phosphate and a vast excess (>11 equiv) of chloroiodomethane to minimize the formation of tetra-tert-butyl methylene bisphosphate[1].

Uses

Used as an intermediate for laboratory research.

Synthesis

Di-tert-butyl (chloromethyl) phosphate, a key compound in the formation of many phosphon-oxymethyl pro-drugs,  is prepared by reacting chloromethyl chlorosulfate (CMCS) with di-tert-butyl potassium phosphate (DTBPP) .

References

[1] Bin Zheng*. “Development of Efficient Processes for the Preparation of Di-tert-butyl Potassium Phosphate and Di-tert-butyl (Chloromethyl) Phosphate.” Organic Process Research & Development 18 5 (2014): 636–642.

Di-tert-butyl Chloromethyl Phosphate(229625-50-7)Related Product Information

• Trimethyl phosphate
• DIMETHYL PHOSPHATE
• Tris(trimethylsilyl)phosphate