Dibenzyl (chloromethyl) phosphate

Base Information

• Chemical Name: Dibenzyl (chloromethyl) phosphate
• CAS No.: 258516-84-6
• Molecular Formula: C15H16ClO4P
• Molecular Weight: 326.716
• European Community (EC) Number: 663-929-6
• DSSTox Substance ID: DTXSID60467418
• Nikkaji Number: J1.721.734H
• Wikidata: Q82294361
• Mol file: 258516-84-6.mol

Synonyms:Dibenzyl (chloromethyl) phosphate;258516-84-6;Dibenzyl chloromethyl phosphate;C15H16ClO4P;MFCD16652586;Phosphoric acid, chloromethyl bis(phenylmethyl) ester;SCHEMBL218693;Dibenzyl(chloromethyl)phosphate;DTXSID60467418;FVTHQGOGQRTOMY-UHFFFAOYSA-N;AMY42265;AKOS016010637;CS-W007628;AS-61264;SY113187;D5828;F20493;A877456;Dibenzyl chloromethyl phosphate, for HPLC derivatisation, >=97.0%, >=97.0% (HPLC)

Chemical Property of Dibenzyl (chloromethyl) phosphate

Chemical Property:

• PSA: 54.57000
• LogP: 4.74100
• Storage Temp.: ?20°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 326.0474737
• Heavy Atom Count: 21
• Complexity: 302

Purity/Quality:

99% ^*data from raw suppliers

Dibenzyl chloromethyl phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COP(=O)(OCC2=CC=CC=C2)OCCl
• 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. Dibenzyl (Chloromethyl) Phosphate acts as a reagent in the screening and synthesis of potent NPP6 inhibitor.

Technology Process of Dibenzyl (chloromethyl) phosphate

There total 5 articles about Dibenzyl (chloromethyl) phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

chlorosulfuric acid chloromethyl ester (49715-04-0) + phosphoric acid dibenzyl ester (1623-08-1) → dibenzyloxy-chloromethylphosphoric acid (258516-84-6)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(02)00707-4

Reference yield: 74.1%

monochloromethanesulfonyl chloride (3518-65-8) + phosphoric acid dibenzyl ester (1623-08-1) → dibenzyloxy-chloromethylphosphoric acid (258516-84-6)

Guidance literature:

With sodium hydrogencarbonate; tetrabutylammonium sulfate; In dichloromethane; water; at 20 ℃; Cooling with ice;

Reference yield: 48.0%

chlorosulfuric acid chloromethyl ester (49715-04-0) + sodium dibenzyl phosphate (97174-13-5) → dibenzyloxy-chloromethylphosphoric acid (258516-84-6)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; water; at 0 - 20 ℃;

upstream raw materials:

chlorosulfuric acid chloromethyl ester

phosphoric acid dibenzyl ester

monochloromethanesulfonyl chloride

silver dibenzylphosphate

Downstream raw materials:

C₃₅H₃₄ClN₂O₈P

C₃₆H₃₁O₈P

{[bis(benzyloxy)phosphoryl]oxy}methyl trans-4-[(1R)-1-(6-{[4-(difluoromethyl)pyridin-2-yl]amino}-4-methyl-2,3'-bipyridin-6'-yl)-1-hydroxyethyl]cyclohexanecarboxylate

Refernces

• 1、 -. "CONJUGATE OF CELL-BINDING RECEPTOR WITH CYTOTOXIC AGENT". Page/Page column 135. . Retrieved 2017/10/31.
• 2、 -. "PHENOL DERIVATIVE AND PREPARATION METHOD AND USE IN MEDICINE THEREOF". Paragraph 1019; 1022; 1023-1025. . Retrieved 2016/10/10.