Diethyl (chloromethyl)phosphonate

Base Information

• Chemical Name: Diethyl (chloromethyl)phosphonate
• CAS No.: 3167-63-3
• Molecular Formula: C5H12ClO3P
• Molecular Weight: 186.575
• Hs Code.: 29319090
• European Community (EC) Number: 221-632-5
• NSC Number: 67753
• UNII: H3LYK2K3U6
• DSSTox Substance ID: DTXSID1062883
• Nikkaji Number: J117.030I
• Wikidata: Q81990324
• Mol file: 3167-63-3.mol

Synonyms:Diethyl (chloromethyl)phosphonate;3167-63-3;Diethyl chloromethylphosphonate;Diethyl chloromethanephosphonate;Phosphonic acid, (chloromethyl)-, diethyl ester;1-[chloromethyl(ethoxy)phosphoryl]oxyethane;Diethyl(chloromethyl)phosphonate;Chloromethylphosphonic acid diethyl ester;AI3-51203;Phosphonic acid, P-(chloromethyl)-, diethyl ester;EINECS 221-632-5;NSC 67753;NSC-67753;Phosphonic acid P -(chloromethyl)-diethyl ester;(Chloromethyl)phosphonic acid diethyl ester;C5H12ClO3P;diethylchloromethylphosphonate;H3LYK2K3U6;NCIOpen2_000726;SCHEMBL431806;C5-H12-Cl-O3-P;DTXSID1062883;NSC67753;Diethyl chloromethylphosphonate, 97%;MFCD00010189;AKOS001012270;1-(chloromethyl-ethoxyphosphoryl)oxyethane;chloromethyl-phosphonic acid diethyl ester;CS-0059172;D4588;EN300-261611;A855098;J-018510;Z56767065

Chemical Property of Diethyl (chloromethyl)phosphonate

Chemical Property:

• Appearance/Colour: Clear colorless to light yellow liquid
• Vapor Pressure: 0.0517mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Boiling Point: 242.9 °C at 760 mmHg
• Flash Point: 74.3 °C
• PSA: 45.34000
• Density: 1.17 g/cm³
• LogP: 2.44880
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 186.0212589
• Heavy Atom Count: 10
• Complexity: 118

Purity/Quality:

98% ^*data from raw suppliers

Diethyl (Chloromethyl)phosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOP(=O)(CCl)OCC
• Uses: Reactant involved in:Subsequent alkylation after nucleophilic substitutionOne-pot alkylation-boration of α-haloalkylphosphonatesSynthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactionsPhosphorylation leading to P-containing cyclopropanesWadsworth-Emmons reactionsRing expansion of zircnacycles via carbenoid insertion

Technology Process of Diethyl (chloromethyl)phosphonate

There total 23 articles about Diethyl (chloromethyl)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: 95.0%

ethanol (64-17-5) + chloromethylphosphonic dichloride (1983-26-2) → diethyl chloromethylphosphonate (3167-63-3)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 2h; Ambient temperature;

Reference yield: 86.0%

diethyl (1-hydroxymethyl)phosphonate (3084-40-0) → diethyl chloromethylphosphonate (3167-63-3)

Guidance literature:

With tetrachloromethane; triphenylphosphine; for 8h; Heating;

DOI:10.1055/s-1990-26992

Reference yield: 80.0%

ethanol (64-17-5) + O,O-bis(trifluoroethyl) chloromethylphosphonate (94080-65-6) → diethyl chloromethylphosphonate (3167-63-3)

Guidance literature:

With lithium; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1039/P19950003125

upstream raw materials:

ethanol

chloromethylphosphonic dichloride

sodium ethanolate

diethyl (1-hydroxymethyl)phosphonate

Downstream raw materials:

ethyl p-nitrophenyl chloromethylphosphonate

Tetraethyl methylenediphosphonate

diethyl ((ethylthio)methyl)phosphonate

diethyl [(phenylthio)methyl]phosphonate

Refernces

• 1、 Touqeer, Saad,Ielo, Laura,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio. "Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes". supporting information. p. 2425 - 2429. Retrieved 2021/04/02.
• 2、 Prevost, Sebastien,Gauthier, Sebastien,De Andrade, Maria Cristina Cano,Mordant, Celine,Touati, Ali Rhida,Lesot, Philippe,Savignac, Philippe,Ayad, Tahar,Phansavath, Phannarath,Ratovelomanana-Vidal, Virginie,Genet, Jean-Pierre. "Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation". experimental part. p. 1436 - 1446. Retrieved 2010/11/03.