107-49-3

Basic information

• Product Name: TEPP
• Synonyms: ea1285;ent18,771;ethylpyrophosphate(et4p2o7);fosvex;grisol;hept;hexamite;killex
• CAS NO: 107-49-3
• Molecular Formula: C₈H₂₀O₇P₂
• Molecular Weight: 290.19
• EINECS: 203-495-3
• Mol File: 107-49-3.mol
• Article Data: 42

Chemical Properties

• Melting Point: 208-213℃ (decomposition)
• Boiling Point: 200℃ (0.3 Torr)
• Flash Point: >100 °C
• Appearance: /solid
• Density: 1.901 g/cm3 (25 ºC)
• Vapor Pressure: 0.0193mmHg at 25°C
• Refractive Index: 1.4270 (20℃)
• 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
• Merck: 13,9279
• CAS DataBase Reference: TEPP(CAS DataBase Reference)
• NIST Chemistry Reference: TEPP(107-49-3)
• EPA Substance Registry System: TEPP(107-49-3)

Safety Data

• Hazard Codes: T+,N
• Statements: 27/28-50
• Safety Statements: 36/37/39-38-45-61
• RIDADR: 3018
• RTECS: UX6825000
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 107-49-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 107-49-3 differently. You can refer to the following data:
1. Water-white to amber liquid depending on purity; hygroscopic. Miscible with water and all organic solvents except aliphatic hydrocarbons; hydrolyzed in water with formation of mono-, di-, and triethyl orthophosphates; water solutions attack metals; commercial material contains 40% TEPP.
2. Tetraethyl pyrophosphate and compressed gas mixture is a liquid charged with a gas. It is a colorless liquid. Its vapor is heavier than air. Faint, fruity, aromatic odor.
3. TEPP is a colorless to amber liquid. Some liquid formulation may contain flammable organic solvents. A solid (glass-like state) below 0C. May be transported in molten form. Faint, fruity, aromatic odor.

Physical properties

Colorless to amber liquid with an agreeable, fruity odor

Uses

Different sources of media describe the Uses of 107-49-3 differently. You can refer to the following data:
1. Insecticide for aphids and mites, rodenticide.
2. Insecticide for mites and aphids; rodenticide.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 637, 1950 DOI: 10.1021/jo01149a031

General Description

Water-white to amber liquid, depending on purity.

Air & Water Reactions

Hygroscopic. Hydrolyzed in water with formation of mono. di, and triethyl orthophosphates, water solutions attack metal surfaces. Reacts slowly with water to form phosphoric acid

Reactivity Profile

Organophosphates, such as TETRAETHYL PYROPHOSPHATE, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Hazard

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.

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Human poison by ingestion and intramuscular routes. Experimental poison by ingestion, skin contact, intraperitoneal, intramuscular, subcutaneous, parenteral, and intravenous routes. Human systemic effects by ingestion, intramuscular, and parenteral routes: paresthesia, wakefulness, excitement, muscle contraction or spasticity, nausea or vomiting and other gastrointestinal changes. The action is sidar to that of parathion: causing an irreversible inhbition of the cholinesterase molecules and the consequent accumulation of large amounts of acetylcholine. Small doses at frequent intervals are largely additive. When heated to decomposition it emits toxic fumes of POx. See also PARATHION.

Potential Exposure

A potential danger to those engaged in the manufacture, formulation and application of this aphicide and acaricide; used as an insecticide to control aphids, thrips, and mites; as an anticholinesterase.

Environmental Fate

Chemical/Physical. Tetraethyl pyrophosphate is quickly hydrolyzed by water. The hydrolysis half-lives at 25 and 38°C are 6.8 and 3.3 hours, respectively (Sittig, 1985).Decomposes at 170–213°C releasing large amounts of ethylene (Hartley and Kidd, 1987; Keith and Walters, 1992).

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3018 Organophosphorus pesticides, liquid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. Note: See T:0305 for TEPP 1compressd gas.

Incompatibilities

Tetraethyl pyrophosphate may be susceptible to formation of highly toxic and flammable phosphine gas in the presence of hydrides and other strong reducing agents. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Hygroscopic. Hydrolyzed in water with formation of mono. di-, and triethyl-orthophosphates. Reacts slowly with cold water forming phosphoric acid. Attacks metals in the presence of water.

Waste Disposal

Return refillable compressed gas cylinders to supplier. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. TEPP is 50% hydrolyzed in water in 6.8 hours @ 25℃, and 3.3 hours @ 38℃; 99% hydrolysis requires 45.2 hours @ 25 ℃, or 21.9 hours @ 38℃. Hydrolysis of TEPP yields nontoxic products. Incineration is, however, an option for TEPP disposal. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C8H20O7P2/c1-5-11-16(9,12-6-2)15-17(10,13-7-3)14-8-4/h5-8H2,1-4H3

Upstream product

• 64-67-5 diethyl sulfate 
• 75-00-3 chloroethane 
• 2303-76-6 sodium diethyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 
• 122-52-1 triethyl phosphite 
• 598-02-7 Diethyl phosphate 
• 64-17-5 ethanol 
• 110907-87-4 O,O,O,O-tetraethyl-sym-monoselenopyrophosphate 
• 91-20-3 naphthalene 
• 116-16-5 1,1,1,3,3,3-hexachloro-propan-2-one 
• 75-65-0 tert-butyl alcohol 
• 108-67-8 1,3,5-trimethyl-benzene 
• 14468-90-7 N-trimethylsilyl-pyrrolidin-2-one 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 311-45-5 paraoxon 
• 78-40-0 triethyl phosphate 
• 74-85-1 ethene 
• 2942-58-7 diethyl cyanophosphonate 
• 598-02-7 Diethyl phosphate 
• 75-00-3 chloroethane 
• 358-74-7 diethyl fluorophosphate 
• 37031-95-1 symm. Diaethyl-diphosphorsaeure-bis-(S-aethyl-isothiuroniumsalz) 
• 1068-21-9 Diethyl phosphoramidate 
• 2404-03-7 diethyl N,N-dimethylphosphoramide 
• 193805-02-6 3-acetamidophenyl diethyl phosphate 
• 5630-71-7 2-chloroethyl diethyl phosphate 
• 53336-82-6 diethyl 3,5-dimethylphenyl phosphate 
• 16519-26-9 diethyl naphthalen-2-yl phosphate 

Relevant articles and documents

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A General Method for the Conversion of Thiophosphoryl and Selenophosphoryl Groups into Phosphoryl Groups by Ozone Oxidation

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ELECTROCHEMICALLY INDUCED PROCESSES OF FORMATION OF PHOSPHORIC ACID DERIVATIVES. 3. ELECTROSYNTHESIS FROM WHITE PHOSPHORUS IN ALCOHOL-WATER SOLUTIONS

It has been established that the process of splitting of the P-P bonds of the white phosphorus molecules is initiated by cathode-generated nucleophiles (HO-, RO-), while functionalization of the P-H bond formed in phosphoric oligomers occurs under the action only of alcohol.The primary product after splitting of all the P-P bonds in phosphoric oligomers is dialkylphosphite (in alcohol-water media), or trialkylphosphite (in absolute alcohol), in the course of electrolysis being transformed into trialkylphosphate.Formation of esters of pyrophosphoric acid with reduced protogenic character of the medium was examined.It is proposed that under these conditions nucleophilic reagents of the type (>P)c-O- form and participate in splitting of the P-P bonds. Keywords: phosphoric acid derivatives, white phosphorus, electrosynthesis, alcohol-water solution.

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Diselenide-Mediated Catalytic Functionalization of Hydrophosphoryl Compounds

We report a diaryldiselenide catalyst for cross-dehydrogenative nucleophilic functionalization of hydrophosphoryl compounds. The proposed organocatalytic cycle closely resembles the mechanism of the Atherton-Todd reaction, with the catalyst serving as a recyclable analogue of the halogenating agent employed in the named reaction. Phosphorus and selenium NMR studies reveal the existence of a P-Se bond intermediate, and structural analyses indicate a stereospecific reaction.

Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates

The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.