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Triethylphosphit
P(OEt)3 · triethyl · PHOSPHOROUS ACID TRIETHYL ESTER · Triethylphosphit · TRIETHYLPHOSPHILE · TRIETHYL PHOSPHONATE · Triethyl Phosphite(TEP) · TRIETHYLPHOSPHITE FOR SYNTHESIS
Identifikatoren & physikalische Daten
| CAS No. | 122-52-1 |
|---|---|
| Summenformel | C6H15O3P |
| Durchschnittliche Molmasse | 166,16 g/mol |
| Monoisotopische Masse | 166,07588097 g/mol |
| SMILES | CCOP(OCC)OCC |
| InChIKey | BDZBKCUKTQZUTL-UHFFFAOYSA-N |
| PubChem CID | 31215 |
| ChEMBL | CHEMBL3186349 |
| EC No. | 204-552-5 |
| DTXSID | DTXSID2026991 |
| Lokaler Name | Triethylphosphit |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 27,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 55,7 |
| Stoffklassen | Other Classes -> Phosphite CompoundsFlammable agents - 2nd degree |
| SpringerMaterials Properties | Schoenflies notation |
| Geruch | Pungent odorCharacteristic, obnoxious phosphite odor |
| Dichte | 0.969 (USCG, 1999) - Less dense than waterwill float0.9629 g at 20 °CRelative density (water = 1): 0.971.413 @25 °C0.969 g/mL at 25 °C(lit.) |
| Color/Form | Colorless liquid |
| Löslichkeit | Soluble in alcohol, etherSolubility in water: reactionChloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly)slightly soluble |
| Flammpunkt | 115 °F (USCG, 1999)54 °C (129 °F) - closed cup54 °C c.c.130 °F |
| Siedepunkt | 311 °F at 760 mmHg (USCG, 1999)157.9 °C157-159 °C156 °C @760 [mm Hg]65 °C |
| Decomposition | The substance decomposes on heating or on burning producing toxic fumes including phosphorous oxides. |
| Schmelzpunkt | -112 °C-112°C |
| Dampfdruck | 1.95 mm Hg at 20 °C<6 hPa (20 °C) |
| Brechungsindex | Index of refraction: 1.4127 at 20 °C/Dn20/D 1.413(lit.) |
| Lagerbedingungen | Flammables area |
| Aggregatzustand | liquid |
| Wichte | 0.969 |
| Farbe | colorless |
| Geruch | characteristic, obnoxious, phosphiteodor |
| Explosionsgrenze | 3.75-42.5%(V) |
| BRN | 956578 |
| Dielektrizitätskonstante | 10.9(65℃) |
| Stabilität | Air Sensitive, Moisture Sensitive |
| InChI | 1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3 |
| InChIKey | BDZBKCUKTQZUTL-UHFFFAOYSA-N |
| SMILES | P(OCC)(OCC)OCC |
| CAS Datenbank | 122-52-1(CAS DataBase Reference) |
| NIST chemische Informationen | Phosphorous acid, triethyl ester(122-52-1) |
| EPA chemische Informationen | Triethyl phosphite (122-52-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (96.2%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 291 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H226: Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Phosphorous acid, triethyl esterPhosphorous acid, triethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorous acid, triethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 22-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/13776Phosphorous acid, triethyl ester: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Phosphorous acid, triethyl ester: Human health tier I assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Special Hazards of Combustion Products: May form hazardous decomposition products. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 54 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable. |
| Gesundheitsgefahren | Exposure to high concentrations may cause headache, nausea, and dizziness due to reduced chlolinesterase activity. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | If left on clothes, can cause reddening of skin[CHRIS] A skin and eye irritant[ICSC] An irritantHarmful if swallowed or inhaled[Sigma-Aldrich MSDS] |
| DOT-Nummer und Handbuch | 2323 130 |
| Reaktive Gruppe | Sulfonates, Phosphonates, and Thiophosphonates, Organic |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: III |
| Special Reports | OECDScreening Information Data Set for Triethyl Phosphite, 122-52-1 (May 2003). A sunnary of exposure to the chemical and its toxicity to humans and the environment. Includes the IUCLID dataset.[Available from, as of July 25, 2016: http://www.inchem.org/documents/sids/sids/122521.pdf]Organization for the Prohibition of Chemical WeaponsConvention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and Their Destruction. The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors.[Available from, as of May 1, 2007: http://www.opcw.org/chemical-weapons-convention/] |
| Reactivity Alerts | Highly Flammable |
| Brandbekämpfung | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:Use powder, foam, carbon dioxide. NO hydrous agents. NO water. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | INHALATION: CALL FOR MEDICAL ASSISTANCE. Remove to fresh air. Treat symptomatically. If not breathing, give artificial respiration.General First Aid: |
| Sichere Lagerung | Fireproof. Dry. Separated from acids and strong oxidants. See Chemical Dangers. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical, or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.In case of fire: cool drums, etc., by spraying with water but avoid contact of the substance with water. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Flammable liquids. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. |
| Freisetung ohne Brand | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: |
| Entsorgungsverfahren | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal companyContaminated packaging: Dispose of as unused product. |
| Verschüttetes entsorgen | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Ökotoxizitätswerte | EC50Species: Scenedesmus subspicatus (Alga)Conditions: static, 21-25 °C, pH 8-10Concentration: >73.6 mg/L for 72 hrEffect: decreased growth rate and biomass /purity 98.8%/ /calculated from diethyl phosphite/LC50Species: Daphnia magna /(water flea)/ age 6-24 hrConditions: static, 19.1-19.4 °CpH 6.9-8Concentration: 94.1 mg/L for 24 hr /calculated from diethyl phosphite/Species: Brachydanio rerio (Fish) age 7 months, length 2.5-3.5 cmConditions: static, 20.9-22.6 °CConcentration: 251.6 mg/L for 96 hr /calculated from diethyl phosphite/ /purity 98.8%/ |
| Umweltverhalten | TERRESTRIAL FATE: Triethyl phosphite hydrolyzes rapidly in the presence of water(1) and, therefore, adsorption to soil, volatilization from moist soil surfaces, and biodegradation are not expected to be important fate processes(SRC). In acid solution (pH = 4), triethyl phosphite hydrolyzes immediately forming diethyl phosphite and ethanol(1). At pH 7, triethyl phosphite hydrolyzes completely within 20 minutesafter 3 hours 89.3% diethyl phosphite and 10.7% monoethyl phosphite are formed(1). At pH 9, the half-life of triethyl phosphite in water is approximately 5.1 hours70% of the substance remains unhydrolyzed after 3 hours(1). Triethyl phosphite is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.95 mm Hg(1). Results of standard biodegradation tests indicate triethyl phosphite is inherently biodegradablehowever, the tests are likely measuring the biodegradability of the hydrolysis products(1,2).AQUATIC FATE: Triethyl phosphite hydrolyzes rapidly in the presence of water(1) and, therefore, adsorption to sediment, volatilization from water surfaces, bioconcentration and biodegradation are not expected to be important fate processes(SRC). In acid solution (pH = 4), triethyl phosphite hydrolyzes immediately forming diethyl phosphite and ethanol(1). At pH 7, triethyl phosphite hydrolyzes completely within 20 minutes70% of the substance remains unhydrolyzed after 3 hours(1). Results of standard biodegradation tests indicate triethyl phosphite is inherently biodegradableATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethyl phosphite, which has a vapor pressure of 1.95 mm Hg at 20 °C(SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethyl phosphite is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 6.6 hours(SRC), calculated from its rate constant of 5.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Triethyl phosphite does not absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour and by ingestion. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Triethyl phosphite is a colorless liquid with a characteristic, obnoxious phosphite odor. It is a chemical intermediate for vinyl phosphate insecticides, for phosphonate insecticidessugarcane ripener. Schedule 3B precursor to dimethyl methylphosphonate, which is a sarin precursor and nerve agent simulant. HUMAN EXPOSURE AND TOXICITY: Human blood monocyte carboxylesterase is inhibited by triethyl phosphite. ANIMAL STUDIES: Triethyl phosphite showed slightly irritating effects on the eyes of 3 male rabbits. All animals showed slight or clearly visible conjunctival erythema in the treated eyes. Slight chemosis and increased secretion were recorded in two animals, each. The findings appeared within one hr and were completely reversible within 48 hr. Six rabbits revealed slightly irritating effects on the skin after 4 hr of semi-occlusive exposure to the undiluted triethyl phosphite. All animals showed slight or clearly visible erythema at the treated sites up to 48 hr after exposure. At day 7, slight erythema still persisted in 5 animals, but had resolved in all but one animal at day 10. None of the animals showed edema at any of the observations. An acute inhalation study was done with male and female rats. After an exposure period of 6 hours the calculated LC50 was 11.6 mg/L for males and 11.1 mg/L for females. A similar study in mice gave LC50 values of 6.2 and 9.2 mg/L for male and female animals, respectively. In both species, signs of toxic stress included eye and upper respiratory irritation, salivation and rapid, shallow breathingmost deaths occurred within 24 hr following treatment. In developmental study doses of 0, 10, 80, 320 and 640 mg/kg bw/day were used for oral administration (gavage) to rats. Groups of 12 male and female rats each were treated (control group: 15 males and 15 females). F0-Animals were treated from 2 weeks before mating to the end of gestation and up to 6 days of lactation. Males were killed after 36 to 37 days of treatment. Females and pups were killed on days 4 to 6 post partum. Ovaries, mammae, testes, epididymides and macroscopically altered tissues of F0 animals were examined histologically. Parameters of general toxicity and fertility, as well as pre- and post-natal development were recorded. In F1, the sex ratio, mortality and weights were not affected by treatment up to and including doses of 80 mg/kg bw/day, while evaluation was not possible at higher doses as there were no surviving pups. No externally malformed pups were observed. The in vivo micronucleus assay in mice was negative. There was no indication of a potential to induce gene mutations in the Ames test with four different strains of Salmonella typhimurium (TA98, TA100, TA1535, TA1537) both with and without metabolic activation. The test was performed including cytotoxic concentrations. |
| Signs and Symptoms | Redness.Redness. Pain.Abdominal pain. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of July 7, 2016: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | Adsorption to soils or suspended solids and sediment is not expected to be an important fate process(SRC) due to the rapid hydrolysis of triethyl phosphite(1). |
| Human Toxicity Excerpts | /ALTERNATIVE and IN VITRO TESTS/ Human blood monocyte carboxylesterase (CBE) is inhibited by a variety of organophosphorus compounds including arylphosphates and arylphosphites and some alkylphosphites. Triphenyl phosphate and triphenyl phosphite with Ki values of 8 x 10(-9) M and 4.8 x 10(-8) M, respectively, are the most potent inhibitors of this enzyme evaluated by this study. The arylphosphates vary in their capacity to inhibit carboxylesterase activity. Diphenyl phosphate with its strong negative charge is not a potent inhibitor (Ki = 1 x 10(-4) M), whereas if its negative charge is neutralized, as in diphenyl methyl phosphate, its capacity to inhibit carboxylesterase is significantly increased. Compounds with increased bulk, such as trinaphthyl phosphate, only inhibit the enzyme at concentrations of 10(-5) M or greater. Arylphosphites have inhibitory capacities similar to the arylphosphates. Alkylphosphites (tributyl phosphite/triethyl phosphite) inhibit carboxylesterase activity, whereas alkylphosphates (tributyl phosphate/triethyl phosphate) have no inhibitory effect. Arylphosphines and arylphosphine oxides do not inhibit carboxylesterase activity. This study demonstrates that organophosphates and organophosphites are relatively effective inhibitors of human monocyte CBE activity with the exception of the alkylphosphates which have no inhibitory activity. We conclude that molecular bulk and charge have a significant role in determining the potency of organophosphorus inhibitors of monocyte CBE. The observed variations in the degree of esterase inhibition by organophosphorus compounds as well as the differences in the pathological expression of neuropathic disorders associated with such chemicals suggest that different esterase enzymes derived from the family of esterase genes may mediate the different neuropathies observed with organophosphorus exposures. Such data also provide the rationale for the kinetic analyses of esterases and the design of non-toxic organophosphorus compounds with low or no monocyte CBE inhibitory capacity to reduce the potential of these commonly used chemicals for human toxicity. |
| Artificial Pollution Sources | Triethyl phosphite's production and use an intermediate for the production of flame retardants, optical brighteners, pesticides, antioxidants, and pharmaceuticals(1,2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: In 2 tests on ready biodegradation, triethyl phosphite was degraded by 49-69%, therefore, it did not reach the criteria for ready biodegradability(1). However, from the degradation curve it can be assumed that hydrolysis was the prerequisite for biodegradation(1). Using OECD Guideline 302C (Inherent Biodegradability: Modified MITI Test II) with an activated sludge inoculum, triethyl phosphite was degraded >100% based on O2 consumption and 73% based on DOC removal classifying the compound as inherently biodegradable(2)the complete disappearance of triethyl phosphite to monoethyl and diethyl phosphite and phosphorous acid in the test system is likely the result of hydrolysis followed by biodegradation(1,2). Biodegradation is not expected to be an important fate process for triethyl phosphite(SRC) due to its hydrolysis(1). |
| Environmental Bioconcentration | Bioconcentration is not expected to be an important fate process(SRC) due to the rapid hydrolysis of triethyl phosphite(SRC). |
| Volatilization from Water/Soil | Volatilization from water surfaces or moist soil is not expected to be an important fate process(SRC) due to the hydrolysis of triethyl phosphite(1). Triethyl phosphite is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.95 mm at 20 °C(1). |
| DHS Chemicals of Interest (COI) | Triethyl phosphite80220Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques. |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 2323 |
| Zollcode | 2920 24 00 |
| RTECS-Nr. | TH1130000 |
| R-Sätze (R) | 10-22-36/37/38-20/22 |
| Toxizität | LD50 orl-rat: 1840 mg/kg JACTDZ 1,218,92 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 16-26-36 |
| Gefahrenklasse | 3Acute Tox. 4 OralAquatic Chronic 3Flam. Liq. 3Skin Sens. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 122-52-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 250 °C |
Anwendungen & Verwendung
Verwenden
Triethyl phosphite is an organophosphorus compound. It is used as a reducing agent; can react with electrophiles to form phosphonates or phosphates; forms a stable complex with copper(I) iodide. Triethyl phosphite is a very good nucleophile. The carbon adjacent to the bromine is the most electrophilic position, and phosphorus is the only nucleophile. Triethyl phosphite displaces the bromine in an SN2-like process, and back attack by the bromide which is released generates a phosphonate product, in which the α-protons are strongly acidic.
Herstellung & Synthese
synthetische
Triethyl phosphite is produced in a closed system by reaction of phosphorous trichlorid and ethanol in the presence of an inorganic or organic base. The product is purified by distillation (Bayer AG, 2002a). Triethyl phosphite is exclusively used as an intermediate for the manufacturing of different products: flame retardants (about 60 %), optical brighteners (about 15 %), pesticides (about 15 %), antioxidants (about 5 %), and pharmaceuticals (about 5 %).