Tetraethyl pyrophosphite

Base Information

• Chemical Name: Tetraethyl pyrophosphite
• CAS No.: 21646-99-1
• Molecular Formula: C8H20 O5 P2
• Molecular Weight: 258.191
• European Community (EC) Number: 244-494-8
• DSSTox Substance ID: DTXSID20176034
• Nikkaji Number: J123.409I
• Wikidata: Q83046370
• Mol file: 21646-99-1.mol

Synonyms:Tetraethyl pyrophosphite;21646-99-1;diethoxyphosphanyl diethyl phosphite;Tetraethyl diphosphite;EINECS 244-494-8;Tetraethyl diphosphite #;Oxybis(diethoxyphosphine);SCHEMBL6994;Tetraethyl pyrophosphite, 96%;DTXSID20176034;Diphosphorous acid, tetraethyl ester;AKOS015916079;FT-0638138;J-014207;7-Hydroxydibenzo[c,f][2,7]naphthyridine-6-carboxylic acid

Chemical Property of Tetraethyl pyrophosphite

Chemical Property:

• Vapor Pressure: 0.0674mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Boiling Point: 237.9°Cat760mmHg
• Flash Point: 115.2°C
• PSA: 73.33000
• Density: g/cm³
• LogP: 3.60280
• Solubility.: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 258.07859773
• Heavy Atom Count: 15
• Complexity: 112

Purity/Quality:

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

Tetraethyl pyrophosphite ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOP(OCC)OP(OCC)OCC
• Uses: Tetraethyl Pyrophosphite is used as a reagent in the preparation of peptides and in the phosphonylation of carbonyl compounds. The product can be used as a reagent for peptide synthesis.

Technology Process of Tetraethyl pyrophosphite

There total 25 articles about Tetraethyl pyrophosphite 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: 81.0%

diethyl phosphorylchloridite (589-57-1) + diethyl hydrogen phosphite (20502-85-6) → diphosphorous acid tetraethyl ester (21646-99-1)

Guidance literature:

With triethylamine; In benzene; at 20 ℃; for 50h;

DOI:10.1007/BF00955842

Reference yield: 68.0%

Diethyl phosphonate (762-04-9,123-22-8) → diphosphorous acid tetraethyl ester (21646-99-1)

Guidance literature:

With sodium iodide; In hexane; acetonitrile; electrochemical oxidation, anodic potential 0.2 -0.3 V, 2.4 A h; Pt anode, Ni cathode; Ag/AgNO₃ reference electrode;

Reference yield: 65.0%

diethyl phosphorylchloridite (589-57-1) + O,O-diethyl (triethoxymethyl)phosphonate (17507-52-7) → diphosphorous acid tetraethyl ester (21646-99-1)

Guidance literature:

at 120 - 130 ℃; for 3.5h;

upstream raw materials:

diethyl phosphorylchloridite

phosphonic acid diethyl ester

O,O-diethyl (triethoxymethyl)phosphonate

diethyl(diethoxymethyl)phosphonate

Downstream raw materials:

diethyl phosphorylchloridite

diethyl (trichloromethyl)phosphonate

diethyl chlorophosphate

α-(diethoxyphosphinyl)benzyl diethyl phosphite

Refernces

• 1、 Kinas, Ryszard W,Okruszek, Andrzej,Stec, Wojciech J. "Reinvestigation of the reaction between sodium diethyl phosphite and diethyl phosphorochloridate. Evidence for a SET process in the formation of a direct P(IV)-P(IV) bond". . p. 7875 - 7879. Retrieved 2007/10/03.
• 2、 Romakhin,Kosachev,Zagumennov,Nikitin. "Free-Radical Phosphorylation of Olefins Initiated by Anodic Oxidation". . p. 227 - 234. Retrieved 2007/10/03.