Di-tert-butyl Chloromethyl Phosphate

CAS NO.：229625-50-7
Empirical Formula: C9H20ClO4P
Molecular Weight: 258.68
MDL number: MFCD12165895
SAFETY DATA SHEET (SDS)
Update Date: 2024-09-26 18:30:47

What is Di-tert-butyl Chloromethyl Phosphate?

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].

The Uses of Di-tert-butyl Chloromethyl Phosphate

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.

Properties of Di-tert-butyl Chloromethyl Phosphate

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
CAS DataBase Reference	229625-50-7

Safety information for Di-tert-butyl Chloromethyl Phosphate

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.