Dibenzyl chloroMethyl phosphate Chemical Properties

Boiling point:

433.2±45.0 °C(Predicted)

Density 

1.285±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

liquid

Appearance

Colorless to light yellow Liquid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

Dibenzyl chloroMethyl phosphate Usage And Synthesis

Uses

Dibenzyl (Chloromethyl) Phosphate acts as a reagent in the screening and synthesis of potent NPP6 inhibitor.

Uses

Synthesis of water-soluble prodrugs of lipophilic alcohols, phenols and amines. Dibenzyl chloromethyl phosphate is an improved derivative of the well known Di-tert-butyl chloromethyl phosphate. So it can be detected more easily by HPLC-UV, because of higher stability, higher yields and better UV-activity.

reaction suitability

reagent type: derivatization reagent
reaction type: Acylations

Synthesis

Step 1: Synthesis of dibenzyl chloromethyl phosphate (33B) Dibenzyl chloromethyl phosphate (33A) (5.0 g, 0.018 mol) was dissolved in a solvent mixture of dichloromethane (50 mL) and water (50 mL), followed by the addition of tetrabutylammonium sulfate (1.22 g, 0.0036 mol) as a phase transfer catalyst. Sodium bicarbonate (6.0 g, 0.072 mol) was slowly added to adjust the pH of the reaction system under cooling conditions in an ice-water bath. Next, chloromethanesulfonyl chloride (2.97 g, 1.9 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction was allowed to partition, the organic phase was separated, and the aqueous phase was extracted with dichloromethane (50 mL). The organic extracts were combined and washed with saturated sodium chloride solution (100 mL x 2) to remove residual water-soluble impurities. The organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using a gradient elution of petroleum ether/ethyl acetate (v/v = 5:1→3:1) to afford dibenzyl chloromethyl phosphate (33B) as a colorless liquid (4.35 g, yield: 74.1%). 1H NMR (400 MHz, CDCl3): δ 7.36-7.26 (m, 10H), 5.63 (d, 2H), 5.10 (d, 4H).

References

[1] Patent: US2016/60197, 2016, A1. Location in patent: Paragraph 0362; 0363; 0364; 0365
[2] Patent: KR2016/5361, 2016, A. Location in patent: Paragraph 1019; 1022; 1023-1025
[3] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 12021 - 12030

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