Diethyl [difluoro(trimethylsilyl)methyl]phosphonate

Base Information

• Chemical Name: Diethyl [difluoro(trimethylsilyl)methyl]phosphonate
• CAS No.: 80077-72-1
• Molecular Formula: C8H19 F2 O3 P Si
• Molecular Weight: 260.293
• DSSTox Substance ID: DTXSID30402997
• Nikkaji Number: J887.714I
• Wikidata: Q82206531
• Mol file: 80077-72-1.mol

Synonyms:80077-72-1;DIETHYL [DIFLUORO(TRIMETHYLSILYL)METHYL]PHOSPHONATE;[diethoxyphosphoryl(difluoro)methyl]-trimethylsilane;MFCD00192024;Diethyl (difluoro(trimethylsilyl)methyl)phosphonate;[Diethoxyphosphoryl(difluoro)methyl]-trimethyl-silane;C8H19F2O3PSi;SCHEMBL14777628;DTXSID30402997;AUYUSSHVQGGCCS-UHFFFAOYSA-N;Phosphonic acid, [difluoro(trimethylsilyl)methyl]-, diethyl ester;AC9835;AKOS017343722;AG-H-21096;SY263879;(Difluoro-trimethylsilanyl-methyl)-phosphonic acid diethyl ester;DIETHYL (DIFLUORO(TRIMETHYLSILYL)METHYL) -PHOSPHONATE;Diethyl [difluoro(trimethylsilyl)methyl]phosphonate, >=85.0% (H-NMR)

Chemical Property of Diethyl [difluoro(trimethylsilyl)methyl]phosphonate

Chemical Property:

• Refractive Index: n20/D 1.414(lit.)
• Boiling Point: 75 °C0.2 mm Hg(lit.)
• Flash Point: 110 °F
• PSA: 45.34000
• Density: 1.077 g/mL at 25 °C(lit.)
• LogP: 4.14260
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 260.08091432
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

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

Diethyl [difluoro(trimethylsilyl)methyl]phosphonate ≥85.0% (H-NMR) ^*data from reagent suppliers

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(=O)(C(F)(F)[Si](C)(C)C)OCC

Technology Process of Diethyl [difluoro(trimethylsilyl)methyl]phosphonate

There total 7 articles about Diethyl [difluoro(trimethylsilyl)methyl]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: 99.0%

(trifluoromethyl)trimethylsilane (81290-20-2) + phosphonic acid diethyl ester (762-04-9) → diethyl difluoro(trimethylsilyl)methylphosphonate (80077-72-1)

Guidance literature:

phosphonic acid diethyl ester; With lithium hydride; lithium chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h; Inert atmosphere; Sealed tube; Glovebox;

(trifluoromethyl)trimethylsilane; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Reagent/catalyst; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1021/acs.orglett.9b00381

Reference yield: 94.0%

chloro-trimethyl-silane (75-77-4) + diethyl (bromodifluoromethyl)phosphonate (65094-22-6) → diethyl difluoro(trimethylsilyl)methylphosphonate (80077-72-1)

Guidance literature:

diethyl (bromodifluoromethyl)phosphonate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/chem.201503354

Reference yield: 88.0%

chloro-trimethyl-silane (75-77-4) + Diethyl difluoromethylphosphonate (1478-53-1) → diethyl difluoro(trimethylsilyl)methylphosphonate (80077-72-1)

Guidance literature:

Diethyl difluoromethylphosphonate; With lithium diisopropyl amide; In tetrahydrofuran; Petroleum ether; at -78 ℃; Inert atmosphere;

chloro-trimethyl-silane; In tetrahydrofuran; Petroleum ether; at -78 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1016/j.jfluchem.2009.02.015

upstream raw materials:

chloro-trimethyl-silane

Diethyl difluoromethylphosphonate

diethyl (bromodifluoromethyl)phosphonate

diethyl difluoromethylphosphonate lithium salt

Downstream raw materials:

[1,1-Difluoro-2-hydroxy-2-(4-nitro-phenyl)-propyl]-phosphonic acid diethyl ester

Phosphoric acid 2,2-difluoro-1-methyl-1-(4-nitro-phenyl)-ethyl ester diethyl ester

diethyl difluoro(4-cyanophenyl)methylphosphonate

diethyl α,α-difluoromethyl-α-(phenyl)phosphonate

Refernces

• 1、 Zi, You,Lange, Markus,Vilotijevic, Ivan. "Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile". supporting information. p. 5689 - 5692. Retrieved 2020/06/19.
• 2、 Das, Manas,O'Shea, Donal F.. "Highly Selective Addition of a Broad Spectrum of Trimethylsilane Pro-nucleophiles to N-tert-Butanesulfinyl Imines". supporting information. p. 18717 - 18723. Retrieved 2016/01/25.