Tetraethyl pyrophosphate

Base Information

• Chemical Name: Tetraethyl pyrophosphate
• CAS No.: 107-49-3
• Molecular Formula: C8H20 O7 P2
• Molecular Weight: 290.19
• Hs Code.: 29199000
• European Community (EC) Number: 203-495-3
• ICSC Number: 1158
• NSC Number: 646213,14707
• UN Number: 3018,2783
• UNII: 28QKT80KX2
• DSSTox Substance ID: DTXSID3034957
• Nikkaji Number: J9.263K
• Wikipedia: Tetraethyl_pyrophosphate
• Wikidata: Q933664
• NCI Thesaurus Code: C163709
• ChEMBL ID: CHEMBL293787
• Mol file: 107-49-3.mol

Synonyms:TEPP;tetraethyl pyrophosphate

Chemical Property of Tetraethyl pyrophosphate

Chemical Property:

• Vapor Pressure: 0.0193mmHg at 25°C
• Melting Point: 208-213℃ (decomposition)
• Refractive Index: 1.4270 (20℃)
• Boiling Point: 260.9 °C at 760 mmHg
• Flash Point: 125.6 °C
• PSA: 99.91000
• Density: 1.205 g/cm³
• LogP: 3.36520
• Storage Temp.: 2-8°C
• Solubility.: Miscible with acetone, benzene, carbon tetrachloride, chloroform, ethanol, ethylene glycol, glycerol, methanol, propylene glycol, toluene, xylene (Windholz et al., 1983), and ethylbenzene.
• Water Solubility.: Miscible
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 290.06842697
• Heavy Atom Count: 17
• Complexity: 246
• Transport DOT Label: Poison

Purity/Quality:

TEPP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by skin contact, inhalation, or ingestion; rapidly absorbed through skin; repeated exposure may, without symptoms, be increasingly hazardous; cholinesterase inhibitor, use may be restricted. TLV: 0.004 ppm. Toxic by skin absorption.
• Hazard Codes: T+,N
• Statements: 27/28-50
• Safety Statements: 36/37/39-38-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCOP(=O)(OCC)OP(=O)(OCC)OCC
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C , on spraying much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the nervous system by a cholinesterase inhibiting effect. See Acute Hazards/Symptoms. This may result in convulsions, respiratory failure, heart failure and death. Medical observation is indicated.
• Effects of Long Term Exposure: Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.
• Physical properties: Colorless to amber liquid with an agreeable, fruity odor
• Uses: Insecticide for aphids and mites, rodenticide. Insecticide for mites and aphids; rodenticide.

Technology Process of Tetraethyl pyrophosphate

There total 81 articles about Tetraethyl pyrophosphate 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: 90.0%

phosphonic acid diethyl ester (762-04-9) → Diethyl phosphate (598-02-7) + Tetraethyl pyrophosphate (107-49-3)

Guidance literature:

With iodosylbenzene; In tetrahydrofuran; for 48h; Heating;

DOI:10.1080/10426500210674

Reference yield: 67.0%

phosphonic acid diethyl ester (762-04-9) + benzylamine (100-46-9) → Tetraethyl pyrophosphate (107-49-3) + diethyl N-benzylphosphoramidate (53640-96-3) + N-benzylidene benzylamine (780-25-6) + benzaldehyde (100-52-7)

Guidance literature:

With copper(l) iodide; oxygen; In acetonitrile; at 55 ℃; for 4h; under 760.051 Torr; Reagent/catalyst;

DOI:10.1039/c3cc45680c

Reference yield: 45.0%

sodium diethyl phosphite (2303-76-6,118080-94-7) → diphosphorous acid tetraethyl ester (21646-99-1) + diphosphorus (III,V)-oic acid tetraethyl ester (682-24-6) + Tetraethyl pyrophosphate (107-49-3) + sodium diethyl phosphate (2870-30-6) + phosphonic acid diethyl ester (762-04-9)

Guidance literature:

With sodium perchlorate; In acetonitrile; Product distribution; Ambient temperature; object of study - electrochemical oxidation at platinum electrode;

upstream raw materials:

pyridine

diethyl ether

Diethyl phosphate

diethyl chlorophosphate

Downstream raw materials:

paraoxon

triethyl phosphate

diethyl naphthalen-1-yl phosphate

triphenylmethylphosphinic acid

Refernces

• 1、 Mukaiyama et al.. "-". . p. 1815. Retrieved 1962.
• 2、 Go??biewska, Justyna,Stawinski, Jacek. "Reaction of Boranephosphonate Diesters with Pyridines or Tertiary Amines in the Presence of Iodine: Synthetic and Mechanistic Studies". . p. 4312 - 4323. Retrieved 2020.
• 3、 Hall,Jacobson. "". . p. 694. Retrieved 1948.
• 4、 Mukaiyama et al.. "". . p. 481. Retrieved 1963.
• 5、 Boiko,Onikiichuk,Yakovenko,Kal'chenko. "New syntheses of 1,1-dichloro-2,2,2-trifluoroethyl isocyanate and its reaction with triethyl phosphite [2]". . p. 1313 - 1314. Retrieved 2002.
• 6、 Cullis, Paul M.,Kaye, Aston D.,Trippett, Stuart. "On the Mechanism of Reaction of Activated Phosphoryl Compounds with Phosphoryl Anions: A Reassessment of the Role of Dioxadiphosphetanes". . p. 1464 - 1466. Retrieved 1987.
• 7、 Huang, Juan,He, Wen,Wang, Bin. "Bu4NI-catalyzed synthesis of pyrophosphate esters from H-phosphonates". . p. 1125 - 1131. Retrieved 2012.
• 8、 Nylen,Stelling. "". . p. 171. Retrieved 1933.
• 9、 Mailahn, Daniela H.,Iarocz, Lucas E.B.,Nobre, Patrick C.,Perin, Gelson,Sinott, Airton,Pesarico, Ana Paula,Birmann, Paloma T.,Savegnago, Lucielli,Silva, Márcio S.. "A greener protocol for the synthesis of phosphorochalcogenoates: Antioxidant and free radical scavenging activities". . . Retrieved 2020/12/07.
• 10、 Chen, Xunwei,Xiao, Zecai,Chu, Hanyu,Wang, Bo,Peng, Ai-Yun. "Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR)3 and its synthetic applications". . p. 6783 - 6790. Retrieved 2018/09/29.