Triethylphosphit

Triethyl phosphite

HCID 31215CAS 122-52-1

Grundinformationen

Standard-SMILES
CCOP(OCC)OCC
InChIKey
BDZBKCUKTQZUTL-UHFFFAOYSA-N
Summenformel
C6H15O3P
Durchschnittliche Molmasse
166,16 g/mol
Monoisotopische Masse
166,07588097

Überblick

Triethyl phosphite appears as a clear colorless liquid with a strong foul odor. Flash point 130 °F. Less dense than water and insoluble in water. Vapors heavier than air.

Namen und Bezeichner

Bevorzugter Name
Triethyl phosphite
IUPAC
triethyl phosphite
Lokaler Name
Triethylphosphit
Englischer Name
Triethyl phosphite
Summenformel
C6H15O3P
Molmasse
166.16

Namen und Synonyme

TRIETHYL PHOSPHITE122-52-1TriethoxyphosphinePhosphorous acid, triethyl esterEthyl phosphite, (EtO)3PFosforyn trojetylowyDTXSID20269916B2R04S55GNSC-5284TRIS(ETHOXY)PHOSPHINEDTXCID506991RefChem:191514
Weitere Namen anzeigen
triethylTriethylphosphitTRIETHYLPHOSPHILETRIETHYL PHOSPHONATETriethyl Phosphite(TEP)TRIETHYLPHOSPHITE FOR SYNTHESISP(EtO)3
204-552-5triethylphosphitePhosphorous Acid Triethyl EsterTriethoxyphosphine-d15MFCD00009084P(OEt)3(C2H5O)3PFosforyn trojetylowy [Czech]

Datenbank-Bezeichner

CAS
122-52-1
PubChem CID
31215
DTXSID
DTXSID2026991
ChEMBL
CHEMBL3186349
UNII
6B2R04S55G
EC Number
204-552-5
Nikkaji
J2.007I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
27,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
6
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Phosphite Compounds

Flammable agents - 2nd degree

SpringerMaterials PropertiesSchoenflies notation
Odor · 2 Einträge

Pungent odor

Characteristic, obnoxious phosphite odor

Density · 4 Einträge

0.969 (USCG, 1999) - Less dense than water; will float

0.9629 g at 20 °C

Relative density (water = 1): 0.97

1.413 @25 °C

Color/FormColorless liquid
Solubility · 2 Einträge

Soluble in alcohol, ether

Solubility in water: reaction

Physikochemische Eigenschaften

Schmelzpunkt
-112 °C · -112°C
Siedepunkt
65 °C · 65 °C
Dichte
0.969 g/mL · 0.969 g/mL at 25 °C(lit.)
Dampfdruck
6 hPa · <6 hPa (20 °C)
Brechungsindex
20 · n20/D 1.413(lit.)
Flammpunkt
130 °F · 130 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H226 (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.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Phosphorous acid, triethyl ester

Phosphorous 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/13776

Phosphorous acid, triethyl ester: Does not have an individual approval but may be used under an appropriate group standard

The 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.)

Other Safety InformationIMAP assessments - Phosphorous acid, triethyl ester: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

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.

Fire PotentialFlammable.
Health Hazards · 2 Einträge

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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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.

First Aid Measures · 4 Einträge

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 .

Accidental Release Measures · 2 Einträge

· 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.

First Aid · 2 Einträge

INHALATION: CALL FOR MEDICAL ASSISTANCE. Remove to fresh air. Treat symptomatically. If not breathing, give artificial respiration.

General First Aid:

Safe StorageFireproof. Dry. Separated from acids and strong oxidants. See Chemical Dangers.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Ecotoxicity Values · 3 Einträge

EC50; Species: Scenedesmus subspicatus (Alga); Conditions: static, 21-25 °C, pH 8-10; Concentration: >73.6 mg/L for 72 hr; Effect: decreased growth rate and biomass /purity 98.8%/ /calculated from diethyl phosphite/

LC50; Species: Daphnia magna /(water flea)/ age 6-24 hr; Conditions: static, 19.1-19.4 °C; pH 6.9-8; Concentration: 94.1 mg/L for 24 hr /calculated from diethyl phosphite/

LC50; Species: Brachydanio rerio (Fish) age 7 months, length 2.5-3.5 cm; Conditions: static, 20.9-22.6 °C; Concentration: 251.6 mg/L for 96 hr /calculated from diethyl phosphite/ /purity 98.8%/

Environmental Fate · 3 Einträge

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 minutes; after 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 hours; 70% 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 biodegradable; however, 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 minutes; after 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 hours; 70% of the substance remains unhydrolyzed after 3 hours(1). Results of standard biodegradation tests indicate triethyl phosphite is inherently biodegradable; however, the tests are likely measuring the biodegradability of the hydrolysis products(1,2).

ATMOSPHERIC 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).

Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Toxicity Summary · 1 Eintrag

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 insecticides; sugarcane 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 breathing; most 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 · 3 Einträge

Redness.

Redness. Pain.

Abdominal pain.

Ongoing Test Status · 1 Eintrag

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/[USEPA; ICSS Dashboard Application; Available from, as of July 7, 2016: http://actor.epa.gov/dashboard/]

Regulatorische Informationen

DHS Chemicals of Interest (COI) · 4 Einträge

Triethyl phosphite

80

220

Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.

Sicherheitsdaten

F
10-23
wgk
1
tsca
TSCA listed
ridadr
UN 2323
hs_code
2920 24 00
RTECS-Nr.
TH1130000

Chemie und Industrie

Verwendung und Herstellung

Uses · 6 Einträge

Used as a plasticizer, additive to grease and resins, sugarcane ripener, and chemical intermediate; [HSDB]

Reagent in synthetic organic chemistry.

Synthesis, plasticizers, stabilizers, lubricants and grease additives.

Plasticizer, vinyl stabilizer, grease additive, color inhibitor for resins

Schedule 3B precursor to dimethyl methylphosphonate /which is a sarin precursor and nerve agent simulant/.

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 %).

U.S. Exports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Imports · 2 Einträge

(1972) No Data

(1975) No Data

U.S. Production · 6 Einträge

2023: <50,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) GREATER THAN 1.36X10+6 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2364]

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Phosphorous acid, triethyl ester. National Production Volume: Withheld.

Consumption Patterns · 1 Eintrag

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 %).

Industry UsesIntermediate
Anwendungen · 1 Eintrag

VerwendenTriethyl 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.

Darstellung · 1 Eintrag

synthetischeTriethyl 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 %).

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