Tetraisopropyl Dichloromethylene Diphosphonate

Base Information

• Chemical Name: Tetraisopropyl Dichloromethylene Diphosphonate
• CAS No.: 10596-22-2
• Molecular Formula: C13H28Cl2O6P2
• Molecular Weight: 413.215
• Hs Code.: 2916190090
• European Community (EC) Number: 600-703-8,430-630-5
• DSSTox Substance ID: DTXSID90400651
• Nikkaji Number: J307.505B
• Wikidata: Q72507146
• ChEMBL ID: CHEMBL310488
• Mol file: 10596-22-2.mol

Synonyms:10596-22-2;Tetraisopropyl Dichloromethylene Diphosphonate;2-[[dichloro-di(propan-2-yloxy)phosphorylmethyl]-propan-2-yloxyphosphoryl]oxypropane;tetraisopropyldichloromethylenebisphosphonate;EC 430-630-5;CHEMBL310488;SCHEMBL3975395;DTXSID90400651;Phosphonic acid, (dichloromethylene)bis-, tetrakis(1-methylethyl) ester;FT-0675075;Tetraisopropyl dichloromethylenebisphosphonate;tetraisopropyl (dichloromethylene)bisphosphonate;J-001513;Tetrapropan-2-yl (dichloromethylene)bis(phosphonate);(Dichloromethylene)bis(phosphonic acid)tetraisopropyl ester;Phosphonic acid,(dichloromethylene)bis-,tetrakis(1-methylethyl)ester(9ci);Phosphonic acid,(dichloromethylene)bis-, tetrakis(1-methylethyl) ester (9CI)

Chemical Property of Tetraisopropyl Dichloromethylene Diphosphonate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 2.07E-06mmHg at 25°C
• Melting Point: 50-51 °C
• Refractive Index: 1.4518
• Boiling Point: 405.3 °C at 760 mmHg
• Flash Point: 310.3 °C
• PSA: 90.68000
• Density: 1.211 g/cm³
• LogP: 6.16150
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 412.0738180
• Heavy Atom Count: 23
• Complexity: 397

Purity/Quality:

99.9% ^*data from raw suppliers

Tetraisopropyl Dichloromethylene Diphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OP(=O)(C(P(=O)(OC(C)C)OC(C)C)(Cl)Cl)OC(C)C
• Uses: An intermediate in the sythesis of Clodronic Acid, Disodium Salt, Tetrahydrate, a biphosphonate bone resorption inhibitor. Tetraisopropyl Dichloromethylene Diphosphonate is an intermediate in the sythesis of Clodronic Acid, Disodium Salt, Tetrahydrate, a biphosphonate bone resorption inhibitor.

Technology Process of Tetraisopropyl Dichloromethylene Diphosphonate

There total 6 articles about Tetraisopropyl Dichloromethylene Diphosphonate 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: 95.0%

Tetraisopropyl methylenediphosphonate (1660-95-3) → tetraisopropyl dichloromethylenebisphosphonate (10596-22-2)

Guidance literature:

With sodium hypochlorite; In water; at 25 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.7b08574

Reference yield:

triisopropyl phosphite (116-17-6) → tetraisopropyl dichloromethylenebisphosphonate (10596-22-2)

Guidance literature:

Multi-step reaction with 2 steps

2: aq. NaOCl, NaCl

With sodium hypochlorite; sodium chloride;

DOI:10.1016/S0022-328X(00)88873-7

Reference yield:

Tetraisopropyl methylenediphosphonate (1660-95-3) → tetraisopropyl dichloromethylenebisphosphonate (10596-22-2) + tetraisopropyl carbonylbisphosphonate (161063-26-9)

Guidance literature:

With formic acid; tert-butylhypochlorite; for 2h; Heating;

upstream raw materials:

Tetraisopropyl methylenediphosphonate

dichlorofluoromethanesulphenyl chloride

triisopropyl phosphite

Downstream raw materials:

dichloromethylenebis(phosphonic acid) mono(tri-n-butylammonium) salt

clodronate

[1-Chloro-1-(diisopropoxy-phosphoryl)-2-phenyl-ethyl]-phosphonic acid diisopropyl ester

Tetraisopropyl methylenediphosphonate

Refernces

• 1、 Yanachkov, Ivan B.,Chang, Hung,Yanachkova, Milka I.,Dix, Edward J.,Berny-Lang, Michelle A.,Gremmel, Thomas,Michelson, Alan D.,Wright, George E.,Frelinger, Andrew L.. "New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors". . p. 204 - 218. Retrieved 2016.
• 2、 Oertell, Keriann,Chamberlain, Brian T.,Wu, Yue,Ferri, Elena,Kashemirov, Boris A.,Beard, William A.,Wilson, Samuel H.,McKenna, Charles E.,Goodman, Myron F.. "Transition state in DNA polymerase β Catalysis: Rate-Limiting chemistry altered by base-pair configuration". . p. 1842 - 1848. Retrieved 2014/04/17.