Diethyl hydrogen phosphite
762-04-9CCO[P+](=O)OCCLXCYSACZTOKNNS-UHFFFAOYSA-NDiethyl phosphonate is a phosphonic ester that is the diethyl ester of phosphonic acid.
762-04-9CHEBI:419621.069 g/cu cm at 25 °C
1.074 @ 20°C
Soluble in water
Soluble in common organic solvents
Soluble in carbon tetrachloride
138 °C
Boiling point: 54 °C at 6 mm Hg
Hazardous decomposition products formed under fire conditions. - Carbon oxides, Oxides of phosphorus
When heated to decomposition it emits toxic fumes of /phosphorous oxides/.
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Danger
H315 (22.5%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 204 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Chemical: Phosphonic acid, diethyl ester
Phosphonic acid, diethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphonic acid, diethyl 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)
REACH registered substance: Diethyl phosphonate (EC: 212-091-6)
Phosphonic acid, diethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Organization for the Prohibition of Chemical Weapons; Convention 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/]
Used as a paint solvent, reducing agent, phosphorylating agent, textile finishing agent, antioxidant, additive for adhesives and extreme pressure lubricants, and intermediate for flame-retardants, insecticides, and other organic phosphorus compounds; Scheduled 3B precursor to VG, sarin, soman, and GF; [HSDB]
Painting (Solvents) [Category: Paint]
Paint solvent, lubricant additive, antioxidant, reducing agent, intermediate for flame-retardants and insecticides, and as a phosphorylating agent
Textile finishing agent
Schedule 3B precursor to VG, sarin, soman, and GF.
(1972) No Data
(1975) No Data
(1972) No Data
(1975) No Data
2023: 250,000 - <550,000 lb
(1972) Probably greater than 4.54x10+5 grams
(1975) Probably greater than 4.54x10+5 grams
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4071]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Phosphonic acid, diethyl ester. Aggregated National Production Volume: < 500,000 pounds.
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Phosphonic acid, diethyl ester. National Production Volume: Withheld.
Synthesis: Phosphorous trichloride and ethanol. Catalyst: NaOH.
Reaction of ethyl alcohol and phosphorus trichloride
All Other Basic Organic Chemical Manufacturing
Phosphonic acid, diethyl ester: ACTIVE
Diethyl phosphite is listed in the CWC /Chemical Weapons Convention/ Annex on Chemicals under Schedule 3.
現在のフィルター条件では反応記録がありません。
読み込み中…
11.2 [mmHg]
11.2 mm Hg at 25 °C
化学的特性colourless liquid
In studies carried out in accordance with current guidelines, neat diethylphosphite has been shown to be mildly irritating to the skin and severely irritating to the eye in rabbits, and to have marked skin sensitizing potential in guinea-pigs.
Strong oxidizing agents, Strong bases, Strong acids, Acid chlorides
/Conditions to avoid/ Heat, flames and sparks.
Interaction /of diethyl phosphite and 4-nitrophenol/ in absence of solvent in a stirred flask heated by a regulated mantle led to a runaway reaction and explosion.
Use water spray to cool unopened containers.
Wear self contained breathing apparatus for fire fighting if necessary.
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
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. Keep in suitable, closed containers for disposal.
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material.
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapours accumulating to form explosive concentrations. Vapors can accumulate in low areas.
12 [mg/m3]
130 [mg/m3]
770 [mg/m3]
/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./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 3 chemicals ... /may/ have been stockpiled or used as weapons, but ... are produced /and used/ in large quantities for purposes not prohibited by the Convention (2). Diethyl phosphite is listed in the CWC Annex on Chemicals under Schedule 3 (1).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that diethyl hydrogen phosphite is expected to have very high mobility in soil(SRC). Volatilization of diethyl hydrdogen phosphite from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.8X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Hydrolysis in moist soil occurs under both acidic and basic conditions(4). Final hydrolysis products include ethanol and phosphorous acid or its salts(4). Diethyl hydrogen phosphite, when released to water, will hydrolyze to the monoester with half-lives of 44 and 87 days at 25 and 20 °C, respectively(5). Diethyl hydrogen phosphite is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 11.2 mm Hg(6). Biodegradation data in soil were not available(SRC, 2013).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a structure estimation method(2), indicates that diethyl hydrdogen phosphite is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 5.8X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.6 and 59 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.15(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis of diethyl phosphite can occur under both acidic and basic conditions(6). Final hydrolysis products include ethanol and phosphorous acid or its salts(1). Diethyl hydrogen phosphite, when released to water, will hydrolyze to the monoester with half-lives of 44 and 87 days at 25 and 20 °C, respectively(7). Shorter half-lives will occur under basic conditions(8,9). Biodegradation data in water were not available(SRC, 2013).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyl hydrogen phosphite, which has a vapor pressure of 11.2 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyl hydrogen 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 7 hours(SRC), calculated from its rate constant of 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diethyl hydrogen phosphite does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of diethyl hydrogen phosphite can be estimated to be 12(SRC). According to a classification scheme(2), this estimated Koc value suggests that diethyl hydrogen phosphite is expected to have very high mobility in soil. Diethyl hydrogen phosphite may leach, possibly reaching groundwater where it will hydrolyze completely(3-7).
Diethyl hydrogen phosphite's production and use as a paint solvent, lubricant additive, antioxidant, reducing agent, intermediate for flame-retardants and insecticide, as a phosphorylating agent(1) and as a Scheduled 3B precursor to several chemical warfare agents(2) may result in its release to the environment through various waste streams(SRC).
An estimated BCF of 3 was calculated in fish for diethyl hydrdogen phosphite(SRC), using an estimated log Kow of -0.15(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
The Henry's Law constant for diethyl hydrdogen phosphite is estimated as 5.8X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that diethyl hydrdogen phosphite is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7.6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 59 days(SRC). Diethyl hydrdogen phosphite's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Diethyl hydrogen phosphite is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 11.2 mm Hg(4).
/LABORATORY ANIMALS: Acute Exposure/ Neat diethylphosphite has been shown to be mildly irritating to the skin and severely irritating to the eye in rabbits, and to have marked skin sensitizing potential in guinea-pigs.
/LABORATORY ANIMALS: Acute Exposure/ Diethylphosphite is of low acute toxicity (LD50 rat oral between 3,500 and 5,560 mg/kg body weight, rat dermal between 5,071 and 5,238 mg/kg body weight).
/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ On 4-week oral administration of diethylphosphite by gavage to rats, the main effect was lung damage, which was possibly treatment-related. The no effect level in this study was 150 mg/kg body weight/day in females and 30 mg/kg body weight/day in males.
/GENOTOXICITY/ Diethylphosphite is not mutagenic in 4 strains in the Salmonella/microsome test with and without metabolic activation at concentrations of up to 5000 ug/plate. It is not clastogenic in the micronucleus test in the mouse.
The rate constant for the vapor-phase reaction of diethyl hydrogen phosphite with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hydrolysis of diethyl phosphite can occur under both acidic and basic conditions(2). Final hydrolysis products include ethanol and phosphorous acid or its salts(2). Diethyl hydrogen phosphite will hydrolyze in water to the monoester (pH unspecified) with half-lives of 44 and 87 days at 25 and 20 °C, respectively(SRC). These half-lives are calculated from kinetic data obtained at higher temperatures (50-98 °C)(3). The monoester has a half-life of 47 days at 25 °C and 85 days at 20 deg(3). Shorter half-lives will occur under basic conditions(4,5). A hydrolysis rate constant of 0.167X10-5 s-1 at 50 °C in water was reported for diethyl hydrogen phosphite(6), corresponding to a half-life of 115 hours(SRC). Diethyl hydrogen phosphite does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(7).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 505 workers (none of these were female) were potentially exposed to diethyl hydrogen phosphite in the US(1). Occupational exposure to diethyl hydrogen phosphite may occur through inhalation and dermal contact with this compound at workplaces where diethyl hydrogen phosphite is produced or used(SRC). Exposure to the general population to diethyl hydrogen phosphite is unlikely, since it is expected to hydrolyze(SRC).
Diethyl hydrogen phosphite's production and use as a paint solvent, lubricant additive, antioxidant, reducing agent, intermediate for flame-retardants and insecticides, as a phosphorylating agent, and as a Scheduled 3B precursor to several chemical warfare agents may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 11.2 mm Hg at 25 °C indicates diethyl hydrogen phosphite will exist solely as a vapor in the atmosphere. Vapor-phase diethyl hydrogen phosphite will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 10 hours. Diethyl hydrogen phosphite does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. If released to soil, diethyl hydrogen phosphite is expected to have very high mobility based upon an estimated Koc of 12. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 5.8X10-6 atm-cu m/mole. Diethyl hydrogen phosphite may volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data in soil or water were not available. If released into water, diethyl hydrogen phosphite is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis occurs under both acidic and basic conditions. Shorter half-lives will occur under basic conditions. Diethyl hydrogen phosphite hydrolyzes to the monoester with half-lives of 44 and 87 days at 25 and 20 °C, respectively. Final hydrolysis products include ethanol and phosphorous acid or its salts. Occupational exposure to diethyl hydrogen phosphite may occur through inhalation and dermal contact with this compound at workplaces where diethyl hydrogen phosphite is produced or used. Exposure to the general population to diethyl hydrogen phosphite is unlikely, since it is expected to hydrolyze. (SRC)
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
LD50 Rat oral 3900 mg/kg
LD50 Rabbit dermal 2165 mg/kg
LD50 rat dermal between 5,071 and 5,238 mg/kg b.w.
LD50 rat oral between 3,500 and 5,560 mg/kg b.w.
/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./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 3 chemicals are like Schedule 1 chemicals in that many have been stockpiled or used as weapons, but different in that they generally are produced in large quantities for purposes not prohibited by the Convention. They are thought to represent a risk to the object of the CWC due to their toxicity or to their importance in producing any of the chemicals listed in Schedule 1 or precursors listed in Schedule 2.
A phosphorus containing substance which is obtained by reacting 3-chloro-1,2,4-thiadiazol-5-yl sulfenyl chloride with diethyl phosphite is effective insecticide, miticide, & antimicrobial agent.
Max permissible air concentration linearly related to lipophilicity of compound.
用途反応中間体
用途医薬、農薬用中間体原料
使用Diethyl phosphite (DEPI) is a versatile reactive intermediate used in the production of various phosphorus based substances. It may be used to prepare the nickel chloride-diethyl phosphite system, efficient catalyst for the cross-coupling reaction between various functionalized arylzinc halides and aryl bromides, triflates and activated chlorides. It may be used: in the stereoselective synthesis of β-fluorinated alkylphosphonates Used in synthesis of homoallylic bromide Used in synthesis of series of carbazole-based α-aminophosphonates used as an extraction agent and phosphate intermediate. Used in synthesis of pesticides kitazine and phosethyl-Al as well as synthetic O, O-diethyl phosphoryl chloride. used for the synthesis of plasticizers, flame retardants, etc. Diethyl phosphite is reported to be chemical warfare agent (CWA) simulant, simulant for nerve agents sarin, soman, tabun, and VX.
一般的な説明Diethyl phosphite is reported to be chemical warfare agent (CWA) simulant, simulant for nerve agents sarin, soman, tabun, and VX.
合成方法エチルアルコール(6.0 mol)のヘキサン溶液を三塩化リン(2.0 mol)のヘキサン溶液に加え,還流させる
定義ChEBI: A phosphonic ester that is the diethyl ester of phosphonic acid.