Bis(dichlorophosphoryl)methane

Base Information

• Chemical Name: Bis(dichlorophosphoryl)methane
• CAS No.: 1499-29-2
• Molecular Formula: CH2 Cl4 O2 P2
• Molecular Weight: 249.785
• Hs Code.: 2931900090
• European Community (EC) Number: 627-821-2
• DSSTox Substance ID: DTXSID10407940
• Nikkaji Number: J658.550G
• Wikidata: Q82213288
• Mol file: 1499-29-2.mol

Synonyms:1499-29-2;Bis(dichlorophosphoryl)methane;Methylenebis(phosphonic dichloride);Phosphonic dichloride, P,P'-methylenebis-;Phosphonic dichloride, methylenebis-;Bis(dichlorophosphonyl)methane;Bis(dichlorophosphinyl)methane;SCHEMBL668667;DTXSID10407940;VRXYCDTWIOCJBH-UHFFFAOYSA-N;Phosphonic dichloride, methylenedi-;methylenebis (phosphonic dichloride);AKOS016012993;Methylenebis(phosphonic dichloride), 97%;CS-0029039;FT-0633613;E78785;EN300-134475;[(dichlorophosphoryl)methyl]phosphonoyl dichloride;J-008643

Chemical Property of Bis(dichlorophosphoryl)methane

Chemical Property:

• Vapor Pressure: 0.00035mmHg at 25°C
• Melting Point: 102-104 °C(lit.)
• Refractive Index: 1.485
• Boiling Point: 329°C at 760 mmHg
• Flash Point: 152.8°C
• PSA: 53.76000
• Density: 1.798g/cm³
• LogP: 4.28530
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 249.825464
• Heavy Atom Count: 9
• Complexity: 157

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methylenebis(phosphonic dichloride) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(P(=O)(Cl)Cl)P(=O)(Cl)Cl

Technology Process of Bis(dichlorophosphoryl)methane

There total 6 articles about Bis(dichlorophosphoryl)methane 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: 48.0%

Tetraisopropyl methylenediphosphonate (1660-95-3) → P,P'-methanediyl-bis-phosphonic acid tetrachloride (1499-29-2)

Guidance literature:

With phosphorus pentachloride; at 80 ℃; for 3h;

Reference yield:

Tetraethyl methylenediphosphonate (1660-94-2) → P,P'-methanediyl-bis-phosphonic acid tetrachloride (1499-29-2)

Guidance literature:

Tetraethyl methylenediphosphonate; With bis(dihydroxyphosphino)-methane; Heating;

With phosphorus pentachloride; Cooling with ice;

DOI:10.1016/j.tetlet.2018.06.022

Reference yield:

Methylenediphosphonic acid (1984-15-2) + methylenediphosphonic acid tetrabutyl ester (6997-56-4) → P,P'-methanediyl-bis-phosphonic acid tetrachloride (1499-29-2)

Guidance literature:

With phosphorus pentachloride;

DOI:10.1021/ja01468a040

upstream raw materials:

Tetraisopropyl methylenediphosphonate

Methylenediphosphonic acid

Tetraethyl methylenediphosphonate

methylenediphosphonic acid tetrabutyl ester

Downstream raw materials:

Methylenediphosphonic acid

methylenediphosphonothioic dichloride

2,2'-methylenebis(5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide)

tetrakis[3-(phenylmethanoyloxy)propyl] methylenebisphosphonate

Refernces

• 1、 Yu, Zhu-Jun,Zhang, Chen,Li, Jiang-Lian,Liu, Yan-Zhao,Yu, Xin-Ling,Guo, Li,Li, Guo-Bo,Wu, Yong. "Rh(III)-catalyzed, 1,2,3-triazole-assisted directed C–H coupling with diazo diphosphonates". supporting information. p. 2816 - 2819. Retrieved 2018/06/19.
• 2、 Althoff, Wolfgang,Fild, Manfred,Schmutzler, Reinhard. "Synthesis and Nuclear Magnetic Resonance Spectroscopic Studies of Alkylene / Alkylidenebis(phosphonic Dihalides) and -bis(fluorophosphoranes)". . p. 1082 - 1090. Retrieved 2007/10/02.