107-49-3

Usage

Uses

Used in Pest Control Industry:
TEPP is used as an insecticide for controlling mites and aphids in agriculture. It is effective in protecting crops from these pests, ensuring a healthy yield.
Used in Rodent Control:
TEPP is also used as a rodenticide, helping to control and eliminate rodent populations in various settings, including agriculture, residential, and commercial areas.
Used in Chemical Industry:
Due to its chemical properties, TEPP can be utilized in the chemical industry for various applications, such as a component in the synthesis of other compounds or as an intermediate in chemical reactions.

Synthesis Reference(s)

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

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

• 110-86-1 pyridine 
• 60-29-7 diethyl ether 
• 598-02-7 Diethyl phosphate 
• 814-49-3 diethyl chlorophosphate 
• 2524-04-1 diethyl phosphorochloridothioate 
• 64-67-5 diethyl sulfate 
• 623-81-4 diethyl sulphite 
• 78-40-0 triethyl phosphate 
• 4697-37-4 ethyl metaphosphate 
• 64-17-5 ethanol 
• 75-00-3 chloroethane 
• 4526-20-9 acetyl diethyl phosphate 
• 650-09-9 O,O-Diethyl O-Trifluoroacetyl Phosphate 
• 2303-76-6 sodium diethyl phosphite 

Downstream Products

• 311-45-5 paraoxon 
• 78-40-0 triethyl phosphate 
• 33650-14-5 diethyl naphthalen-1-yl phosphate 
• 166660-56-6 triphenylmethylphosphinic acid 
• 99981-31-4 diethoxyphosphoryloxy-carbamic acid phenyl ester 
• 598-02-7 Diethyl phosphate 
• 4697-37-4 ethyl metaphosphate 
• 1707-71-7 Diethylpyrophosphat 
• 74-85-1 ethene 
• 16519-26-9 diethyl naphthalen-2-yl phosphate 
• 53336-82-6 diethyl 3,5-dimethylphenyl phosphate 
• 5630-71-7 2-chloroethyl diethyl phosphate 
• 193805-02-6 3-acetamidophenyl diethyl phosphate 
• 2404-03-7 diethyl N,N-dimethylphosphoramide 

Relevant academic research and scientific papers

Reaction of Boranephosphonate Diesters with Pyridines or Tertiary Amines in the Presence of Iodine: Synthetic and Mechanistic Studies

Boranephosphonate diesters react with heteroaromatic and certain tertiary amines in the presence of an oxidant (I2) to afford the boron-modified phosphodiester analogues containing a P-B-N structural motif. Our multinuclear 31P and 11B NMR spectroscopy studies lend support for a two-step mechanism involving generation of a λ3-boranephosphonate intermediate that immediately coordinates an amine in the solvent cage, leading to B-pyridinium or B-ammonium boranephosphonate betaine derivatives. We found that the type of the solvent used (e.g., dichloromethane vs acetonitrile) significantly affected the course of the reaction, resulting in either formation of boron-modified derivatives or loss of the boron group with a subsequent oxidation of the phosphorus atom. In aprotic, electron-donating, polar solvents., e.g., acetonitrile (ACN) and tetrahydrofuran (THF), a λ3-boranephosphonate intermediate can also coordinate solvent molecules forming P-B-ACN or P-B-THF complexes that may influence the type of the products formed.

On the Mechanism of Reaction of Activated Phosphoryl Compounds with Phosphoryl Anions: A Reassessment of the Role of Dioxadiphosphetanes

Activated phosphoryl compounds react with phosphoryl anions to give anhydrides without the intervention of dioxadiphosphetane intermediates; the mechanism has been probed using oxygen isotopes and high field 31P n.m.r. spectroscopy.

Bu4NI-catalyzed synthesis of pyrophosphate esters from H-phosphonates

A n-Bu4NI/t-BuOOH catalysis system has been developed to promote oxidative dehydrogenative coupling of H-phosphonates to form pyrophosphate tetraesters. This novel iodide (I) ion-catalyzed reaction provides easy access to pyrophosphate derivatives in the absence of a metal and solvent. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Taylor and Francis Group, LLC.

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.

A greener protocol for the synthesis of phosphorochalcogenoates: Antioxidant and free radical scavenging activities

In this contribution, a metal- and base-free protocol has been developed for the synthesis of phosphorochalcogenoates (Se and Te) by using DMSO as solvent at 50 °C. A variety of phosphorochalcogenoates were prepared from diorganyl dichalcogenides and H-phosphonates, leading to the formation of a Chal-P(O) bond, in a rapid procedure with good to excellent yields. A full structural elucidation of products was accessed by 1D and 2D NMR, IR, CGMS, and HRMS analyses, and a stability evaluation of the phosphorochalcogenoates was performed for an effective operational description of this simple and feasible method. Typical 77Se{1H} (δSe = 866.0 ppm), 125Te{1H} (δTe = 422.0 ppm) and 31P{1H} (δP = ?1.0, ?13.0 and ?15.0 ppm) NMR chemical shifts were imperative to confirm the byproducts, in which this stability study was also important to select some products for pharmacological screening. The phosphorochalcogenoates were screened in vitro and ex vivo tests for the antioxidant potential and free radical scavenging activity, as well as to investigation toxicity in mice through of the plasma levels of markers of renal and hepatic damage. The pharmacological screening of phosphorochalcogenoates indicated that compounds have antioxidant propriety in different assays and not changes plasma levels of markers of renal and hepatic damage, with excision of 3g compound that increased plasma creatinine levels and decreased plasma urea levels when compared to control group in the blood mice. Thus, these compounds can be promising synthetic antioxidants that provide protection against oxidative diseases.

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.

Reinvestigation of the iodine-mediated phosphoramidation reaction of amines and P(OR)3 and its synthetic applications

A systematic study on the iodine-mediated phosphoramidation reaction of amines and trialkyl phosphites was conducted, which not only disclosed the factors affecting the reaction but also revealed that it could proceed smoothly in CH2Cl2 at room temperature in open air. Using this method, various phosphoramidates with different aliphatic amines and aromatic amines were synthesized in good to excellent yields. Our present investigation shows that this underused method is actually a mild, practical and general way to synthesize phosphoramidates and will have wide applications.

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.

Copper-catalyzed aerobic oxidative trifluoromethylation of h-phosphonates using trimethyl(trifluoromethyl)silane

Copper-catalyzed aerobic oxidative trifluoromethylation of readily accessible H-phosphonates was demonstrated for the first time. This method not only provides an alternative method for the facile synthesis of a series of biologically important CFphosphonates, but also demonstrates the first example of the efficient construction of a P-CFbond via transition-metal catalysis.

Selective P-P and P-O-P bond formations through copper-catalyzed aerobic oxidative dehydrogenative couplings of H-phosphonates

(Chemical Equation Presented) Different copper complexes selectively catalyze the aerobic oxidative coupling of H-phosphonates to afford either hypophosphates and pyrophosphates in high yields with high selectivity (see scheme; tmeda = N, N, N', N'-tetramethylethylenediamine).