Diethyl (difluoromethyl)phosphonate

Base Information

• Chemical Name: Diethyl (difluoromethyl)phosphonate
• CAS No.: 1478-53-1
• Molecular Formula: C5H11 F2 O3 P
• Molecular Weight: 188.111
• Hs Code.: 29319090
• European Community (EC) Number: 673-917-2
• DSSTox Substance ID: DTXSID20163803
• Nikkaji Number: J879.040J
• Wikidata: Q83032790
• ChEMBL ID: CHEMBL5207763
• Mol file: 1478-53-1.mol

Synonyms:1478-53-1;Diethyl (difluoromethyl)phosphonate;Difluoromethylphosphonic acid diethyl ester;diethyl (difluoromethane)phosphonate;diethyl difluoromethanephosphonate;diethyl difluoromethylphosphonate;1-[difluoromethyl(ethoxy)phosphoryl]oxyethane;Phosphonic acid, (difluoromethyl)-, diethyl ester;C5H11F2O3P;DIFLUOROMETHYLPHOSPHONICACIDDIETHYLESTER;MFCD00192023;Phosphonic acid,P-(difluoromethyl)-, diethyl ester;Diethyl(difluoromethyl)phosphonate;SCHEMBL193239;CHEMBL5207763;DTXSID20163803;diethyl difluoromethane phosphonate;diethyl(difluoromethyl)-phosphonate;diethyl-(difluoromethyl)-phosphonate;C5-H11-F2-O3-P;AKOS005216219;AS-68783;Diethyl (difluoromethyl)phosphonate, 97%;DifluoroMethylphosphonic acidDiethyl ester;SY062739;1-(difluoromethyl-ethoxyphosphoryl)oxyethane;difluoromethyl phosphonic acid diethyl ester;Difluoromethyl-phosphonic acid diethyl ester;CS-0094054;FT-0649833;(Difluoromethyl)phosphonic acid, diethyl ester;(difluoromethyl) phosphonic acid, diethyl ester;C13418;EN300-100935;A808702;1-[bis(fluoranyl)methyl-ethoxy-phosphoryl]oxyethane;J-008420;Phosphonic acid, P-(difluoromethyl)-, diethyl ester

Chemical Property of Diethyl (difluoromethyl)phosphonate

Chemical Property:

• Vapor Pressure: 1.29mmHg at 25°C
• Refractive Index: n20/D 1.388(lit.)
• Boiling Point: 179.2°Cat760mmHg
• Flash Point: 62.2°C
• PSA: 45.34000
• Density: 1.181g/cm³
• LogP: 2.47510
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 188.04138753
• Heavy Atom Count: 11
• Complexity: 141

Purity/Quality:

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

Diethyl Difluoromethanephosphonate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 34
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(F)F)OCC
• Uses: Inhibitor of bacterial phosphotriesterases and an intermediate for the synthesis of 5’-diphosphate/5’-triphosphate mimics for transcriptase and glycerol kinase inhibition.

Technology Process of Diethyl (difluoromethyl)phosphonate

There total 54 articles about Diethyl (difluoromethyl)phosphonate 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: 88.0%

Chlorodifluoromethane (75-45-6) + phosphonic acid diethyl ester (762-04-9) → Diethyl difluoromethylphosphonate (1478-53-1)

Guidance literature:

phosphonic acid diethyl ester; With sodium; In tetrahydrofuran; at 20 ℃; for 24h;

Chlorodifluoromethane; In tetrahydrofuran; for 15h;

DOI:10.1021/jo051511c

Reference yield: 86.0%

trimethyl(difluoromethyl)silane (65864-64-4) + diethyl chlorophosphate (814-49-3) → Diethyl difluoromethylphosphonate (1478-53-1)

Guidance literature:

With potassium 2-methylbutan-2-olate; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 4h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/d1ob00273b

Reference yield: 72.0%

4-methoxybenzenediazonium tetrafluoroborate (459-64-3) + diethyl difluoro(trimethylsilyl)methylphosphonate (80077-72-1) → Diethyl difluoromethylphosphonate (1478-53-1) + diethyl α,α-difluoro-4-methoxybenzylphosphonate

Guidance literature:

diethyl difluoro(trimethylsilyl)methylphosphonate; With copper(I) thiocyanate; cesium fluoride; In acetonitrile; at 0 - 40 ℃; for 2h; Glovebox; Sealed tube; Inert atmosphere;

4-methoxybenzenediazonium tetrafluoroborate; In acetonitrile; at 20 ℃; for 16h; Reagent/catalyst; Solvent; Catalytic behavior; Glovebox; Sealed tube; Inert atmosphere;

DOI:10.1002/chem.201703542

upstream raw materials:

Chlorodifluoromethane

sodium diethyl phosphite

phosgene

[(diethoxyphosphoryl)difluoromethyl]zinc bromide

Downstream raw materials:

(1,1-Difluoro-2-phenoxythiocarbonyloxy-octyl)-phosphonic acid diethyl ester

[1,1-Difluoro-2-((3aR,4S,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2-phenoxythiocarbonyloxy-ethyl]-phosphonic acid diethyl ester

β,β-difluoro-α-methylstyrene

Tetraethyl difluoromethylenediphosphonate

Refernces

• 1、 Burton, Donald J.,Flynn, Richard M.. "PREPARATION OF F-METHYLENE BIS PHOSPHONATES". . p. 263 - 266. Retrieved 1980.
• 2、 Levin, Vitalij V.,Elkin, Pavel K.,Struchkova, Marina I.,Dilman, Alexander D.. "Nucleophilic fluoroalkylation of (bromomethyl)pinacolborane using silicon reagents". . p. 43 - 46. Retrieved 2013.
• 3、 Burton, Donald J.,Yang, Zhen-Yu. "Fluorinated organometallics: Perfluoroalkyl and functionalized perfluoroalkyl organometallic reagents in organic synthesis". . p. 189 - 275. Retrieved 1992.
• 4、 Nair, Haridasan K.,Guneratne, Ranil D.,Modak, Anil S.,Burton, Donald J.. "Synthesis of Novel Fluorinated Bisphosphonates and Bisphosphonic Acids". . p. 2393 - 2398. Retrieved 1994.
• 5、 Krishnamurti, Vinayak,Barrett, Colby,Prakash, G. K. Surya. "Siladifluoromethylation and Deoxo-trifluoromethylation of PV-H Compounds with TMSCF3: Route to PV-CF2- Transfer Reagents and P-CF3 Compounds". . p. 1526 - 1529. Retrieved 2019/03/07.