Diethyl phosphonate

Base Information

• Chemical Name: Diethyl phosphonate
• CAS No.: 762-04-9
• Molecular Formula: C4H11O3P
• Molecular Weight: 138.103
• Hs Code.: 29209014
• European Community (EC) Number: 212-091-6
• NSC Number: 2665
• UNII: U9X9YBA22W
• Wikipedia: Diethylphosphite
• Wikidata: Q63409686
• Mol file: 762-04-9.mol

Synonyms:Diethyl phosphonate;762-04-9;diethylphosphite;Phosphonic acid, diethyl ester;Phosphonic acid diethyl ester;Hydrogen diethyl phosphite;Diethyl acid phosphite;Diethoxyphosphine oxide;O,O-Diethyl phosphonate;DIETHYL HYDROGEN PHOSPHITE;Phosphorous acid, diethyl ester;diethoxy(oxo)phosphanium;Ethyl phosphonate ((EtO)2HPO);Diethylfosfit [Czech];Diethylfosfit;Diethylphosphonate;NSC 2665;DIETHYLPHOSPHONO GROUP;HSDB 2591;EINECS 212-091-6;UNII-U9X9YBA22W;BRN 0605759;U9X9YBA22W;NSC-2665;EC 212-091-6;diethoxyphosphino-1-one;2o7v;phosphonate diethyl ester;Diethyl phosphite, 98%;D06SWV;1-Ethoxyphosphonoyloxyethane;WLN: 2OPQO2;(EtO)2P(O)H;SCHEMBL35436;OPH(OC2H5)2;1-ethoxy-phosphonoyloxy-ethane;CHEBI:41962;NSC2665;LXCYSACZTOKNNS-UHFFFAOYSA-N;AKOS009028914;AKOS032949756;DB02811;DIETHYL HYDROGEN PHOSPHITE [HSDB];Diethyl phosphite, technical grade, 94%;BP-20528;LS-109007;D0521;FT-0649553;Q63409686

Chemical Property of Diethyl phosphonate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.383mmHg at 25°C
• Melting Point: -70 °C
• Refractive Index: n20/D 1.407(lit.)
• Boiling Point: 204.072 °C at 760 mmHg
• Flash Point: 82.222 °C
• PSA: 59.00000
• Density: 1.072g/mLat 25°C(lit.)
• LogP: 1.44910
• Sensitive.: Moisture Sensitive
• Water Solubility.: miscible (hydrolysis)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 137.03675617
• Heavy Atom Count: 8
• Complexity: 65.7

Purity/Quality:

99.9% ^*data from raw suppliers

Diethyl phosphite ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36/37/39-37/39-28-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphite Compounds
• Canonical SMILES: CCO[P+](=O)OCC
• Uses: Diethyl phosphite (DEPI) is a versatile reactive intermediate used in the production of various phosphorus based substances. It may be used to prepare the nickel chloride-diethyl phosphite system, efficient catalyst for the cross-coupling reaction between various functionalized arylzinc halides and aryl bromides, triflates and activated chlorides. It may be used: in the stereoselective synthesis of β-fluorinated alkylphosphonates Used in synthesis of homoallylic bromide Used in synthesis of series of carbazole-based α-aminophosphonates used as an extraction agent and phosphate intermediate. Used in synthesis of pesticides kitazine and phosethyl-Al as well as synthetic O, O-diethyl phosphoryl chloride. used for the synthesis of plasticizers, flame retardants, etc. Diethyl phosphite is reported to be chemical warfare agent (CWA) simulant, simulant for nerve agents sarin, soman, tabun, and VX. Diethyl phosphite is precursor used for the synthesis of various organophosphorus compounds. used to prepare the nickel chloride-diethyl phosphite system, efficient catalyst for the cross-coupling reaction between various functionalized arylzinc halides and aryl bromides, triflates and activated chlorides.

Technology Process of Diethyl phosphonate

There total 238 articles about Diethyl 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: 73.0%

Phosphorous acid diethyl ester (E)-1-ethyl-but-2-enyl ester → (2E,4E)-hexa-2,4-diene (5194-51-4) + 1,3-hexadiene (20237-34-7) + phosphonic acid diethyl ester (762-04-9)

Guidance literature:

With nickel dichloride; at 85 ℃; for 35h; Yield given;

DOI:10.1016/S0022-328X(00)99689-X

Reference yield: 64.0%

benzylamine (100-46-9) + diethyl acetylphosphonate (919-19-7) → (1-Hydroxyethylidene)-1,1-bisphosphonic acid tetraethyl ester (20427-93-4) + N-(phenylmethyl)acetamide (588-46-5) + phosphonic acid diethyl ester (762-04-9)

Guidance literature:

In diethyl ether; for 1h; Ambient temperature;

DOI:10.1021/jo01309a019

Reference yield: 43.0%

diethyl benzoylphosphonate (3277-27-8) + phenethylamine (64-04-0) → diethyl 1-(diethylphosphoryloxy)-1-phenylmethylphosphonate (18104-91-1) + N-phenethylbenzamide (3278-14-6) + phosphonic acid diethyl ester (762-04-9)

Guidance literature:

In diethyl ether; for 1h; Ambient temperature;

DOI:10.1021/jo01309a019

upstream raw materials:

Diazoethan

2-chloro-4-methyl-dioxaphospholane

ethanol

diphosphorus (III,V)-oic acid tetraethyl ester

Downstream raw materials:

(piperidin-1-ylmethyl)phosphonic acid diethyl ester

diethyl chlorophosphate

diethyl 1-amino-2-phenyl-1-ethylphosphonate hydrochloride

diethyl (hydroxy)(2-chlorophenyl)methylphosphonate

Refernces

• 1、 Silver,Luz. "-". . p. 1091,1092. Retrieved 1962.
• 2、 Stano, Adrian,Mucha, Artur,Kafarski, Pawel. "Reaction of N-(benzyloxycarbonyl)aminobenzylphosphonous acid with ethyl orthoformate". . p. 4269 - 4277. Retrieved 1999.
• 3、 Fernández-Pérez, Héctor,Lenartowicz, Pawe?,Carreras, Lucas,Grabulosa, Arnald,Kafarski, Pawe?,Vidal-Ferran, Anton. "Access to α-aminophosphonic acid derivatives and phosphonopeptides by [Rh(P-OP)]-catalyzed stereoselective hydrogenation". . p. 14779 - 14784. Retrieved 2020.
• 4、 Ikaev,Polezhaeva,Mingalev,Lisichkin. "Reaction of diethyl butane-1-phosphonate with the surface of tin dioxide". . p. 417 - 420. Retrieved 2008.
• 5、 -. "Novel synthetic method of diethyl phosphite". Paragraph 0022-0032. . Retrieved 2021/09/15.
• 6、 Yang, Ling,Tan, Dong-Hang,Fan, Wen-Xin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen. "Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates". supporting information. p. 3454 - 3458. Retrieved 2020/12/17.