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Home > Encyclopedia > O,O-Diethyl phosphorochloridothioate

O,O-Diethyl phosphorochloridothioate

O,O-Diethyl phosphorochloridothioate structure

O,O-Diethyl phosphorochloridothioate 

structure
  • CAS No:

    2524-04-1

  • Formula:

    C4H10ClO2PS

  • Chemical Name:

    O,O-Diethyl phosphorochloridothioate

  • Synonyms:

    Phosphorochloridothioic acid,O,O-diethyl ester;Ethyl phosphorochloridothioate ((EtO)2ClPS);Diethyl chlorothiophosphate;O,O-Diethyl phosphorochloridothioate;O,O-Diethyl phosphorochlorothioate;Diethyl phosphorochloridothioate;Diethyl phosphorochlorothioate;Diethyl thiophosphoryl chloride;O,O-Diethyl chlorothiophosphate;O,O-Diethyl chlorothiophosphonate;O,O-Diethyl phosphorothionochloridate;O,O-Diethyl thiophosphoryl chloride;Diethyl phosphorothiochloridate;O,O-Diethyl chlorothionophosphate;O,O-Diethyl thionophosphoric chloride;O,O-Diethyl thionophosphoryl chloride;O,O-Diethyl thiophosphorochloridate;O,O-Diethyl chloridothionophosphate;O,O-Diethyl phosphorothiochloridate;O,O-Diethyl thionophosphorochloridate;O,O-Diethyl chloridophosphorothioate;Diethoxythiophosphoryl chloride;Diethyl phosphorothionochloridate;O,O-Diethyl thiophosphoric acid chloride;(Chlorodiethoxy)phosphine sulfide;O,O-Diethyl chlorophosphorothioate;NSC 43776;1081841-50-0

  • Categories:

    Biochemical Engineering  >  Nucleoside Drugs

Description

CLEAR COLORLESS TO LIGHT YELLOW LIQUID


Diethylthiophosphoryl chloride appears as a colorless to light amber liquid with a disagreeable odor. Insoluble in water but soluble in most organic solvents. May be highly toxic and irritating to the eyes and lungs. Used as an intermediate for pesticides, as an oil and gasoline additive, and as a flame retardant.|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Diethylthiophosphoryl chloride appears as a colorless to light amber liquid with a disagreeable odor. Insoluble in water but soluble in most organic solvents. May be highly toxic and irritating to the eyes and lungs. Used as an intermediate for pesticides, as an oil and gasoline additive, and as a flame retardant.

O,O-Diethyl phosphorochloridothioate Basic Attributes

188.61

188.61

219-755-4

A310QMF5Q0

0448

43776

2751

DTXSID5027487

COLORLESS TO LIGHT AMBER LIQUID

2931900090

Characteristics

50.6

3.17330

Diethylthiophosphoryl chloride appears as a colorless to light amber liquid with a disagreeable odor. Insoluble in water but soluble in most organic solvents. May be highly toxic and irritating to the eyes and lungs. Used as an intermediate for pesticides, as an oil and gasoline additive, and as a flame retardant.

1.196 g/cm3 @ Temp: 25 °C

-75 °C

110 °C

>230 °F

n20/D 1.472(lit.)

hydrolyzes, immiscible

Keep away from sources of ignition. Store in a cool, dry place. Store in a tightly closed container. Corrosives area.

1.4 mm Hg ( 50 °C)

Oral-rat LD50:1340 mg/kg; Oral-Mouse LD50: 800 mg/kg

Combustible

Highly flammable. Insoluble in water but soluble in most organic solvents. Contact with moisture in the air produces highly corrosive and toxic fumes containing hydrogen chloride. Decomposes in water producing acidic products.

Acyl Halides, Sulfonyl Halides, and Chloroformates

Highly Flammable

DIETHYLTHIOPHOSPHORYL CHLORIDE is incompatible with bases (including amines), with strong oxidizing agents, and with alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Safety Information

II

8

UN 2751 8/PG 2

3

23/24/25-34-26-21/22

23-26-36/37/39-45-28A

TD1780000

T,T+

The warehouse is ventilated, low temperature and dry; stored separately from alkali and oxidant

STABLE AT ROOM TEMP; SLOWLY ISOMERIZES AT 100 DEG C

P261-P280-P301 + P310-P305 + P351 + P338-P310

H301-H311-H314-H331

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H301 (27.94%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 136 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P260, P264, P270, P271, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P320, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: Note: Most foams will react with the material and release corrosive/toxic gases. CAUTION: For Acetyl chloride (UN1717), use CO2 or dry chemical only. SMALL FIRE: CO2, dry chemical, dry sand, alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. FOR CHLOROSILANES, DO NOT USE WATER; use AFFF alcohol-resistant medium-expansion foam. Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor-suppressing foam may be used to reduce vapors. FOR CHLOROSILANES, use AFFF alcohol-resistant medium-expansion foam to reduce vapors. DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. SMALL SPILL: Cover with DRY earth, DRY sand or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean, non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal. (ERG, 2016)

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)

IF SOLN OF.../ACIDS/ ARE SPILLED...1. COLLECT OR CONFINE SPILLED MATERIAL IN THE MOST CONVENIENT & SAFE MANNER. 2. IF POSSIBLE, RECLAIM THE SPILLED MATERIAL. IF THIS IS NOT POSSIBLE; 3. DILUTE &/OR NEUTRALIZE & DISPOSE OF IN A SECURED SANITARY LANDFILL. /HYDROCHLORIC ACID/|NEUTRALIZING AGENTS...: FLUSH WITH WATER; APPLY POWDERED LIMESTONE, SLAKED LIME, SODA ASH, OR SODIUM BICARBONATE. /HYDROCHLORIC ACID/

Personal protection: complete protective clothing including self-contained breathing apparatus. 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.

Separated from food and feedstuffs. Dry.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is corrosive to the eyes, skin and respiratory tract. Inhalation of the vapour may cause lung oedema. The effects may be delayed. Medical observation is indicated.

Cholinesterase inhibition. Cumulative effects are possible. See Acute Hazards/Symptoms.

NO open flames. NO contact with hot surfaces.

PREVENT GENERATION OF MISTS! IN ALL CASES CONSULT A DOCTOR!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles, face shield or eye protection in combination with breathing protection.

Toxicity

moderately toxic

Drug Information

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Corrosives

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)


Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.


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.

...IRRITANT TO EYES & LUNGS.

DECTP

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Burning sensation. Cough. Shortness of breath. Sore throat. Symptoms may be delayed.


MAY BE ABSORBED! Redness. Burning sensation. Pain. Blisters. Further see Inhalation.


MAY BE ABSORBED! Redness. Pain. Blurred vision. Loss of vision. Severe deep burns.

O,O-Diethyl phosphorochloridothioate Use and Manufacturing

Methods of Manufacturing

At present, the domestic industrial production of ethyl chloride mainly adopts the phosphorus pentasulfide method, that is, the phosphorus pentasulfide is first reacted with ethanol to produce ethyl sulfide, and then chlorinated to obtain ethyl chloride. The by-product sulfur chloride can be decomposed by sodium sulfite. However, this method consumes a large amount of sodium sulfite, the production equipment is huge, and a large amount of wastewater is generated, and the treatment of the three wastes is difficult. Therefore, the new process uses sodium sulfide to decompose sulfur chloride, which improves the quality of chloride and the purity can reach more than 97%. S2Cl2+Na2S→2NaCl+3S↓ The required sodium sulfide is obtained from the absorption of hydrogen sulfide in the exhaust gas of the previous process by caustic soda. The precipitated sulfur is crystalline and can be used to produce sulfuric acid or phosphorus pentasulfide. The specific process is as follows: the ethyl sulfide prepared by the phosphorus pentasulfide route is pumped into the chlorination reactor, stirred and cooled to 15 ℃, start the chlorine gas, control the chlorination temperature at 25 ~ 28 ℃ (30 ~ 35 ℃ in winter) ), the speed of chlorine gas is about 40-50kg/h, and the pressure of chlorine gas is about 0.1kPa. The generated hydrogen chloride gas is neutralized and discharged through lime. After 1 hour of reaction, crude ethyl chloride is obtained, with a content of 63% to 67%, and a yield of about 94%. Then add the crude ethyl chloride product to the fine ethyl chloride product, add a composite co-catalyst, drop 18% aqueous sodium sulfide solution at a temperature of 5-25°C, and keep the reaction at 5-30°C for 10-20 minutes after the addition is completed. The refined liquid is filtered and layered, and the oil layer is rinsed with clean water to obtain a fine product with a content of 96% to 98%, free of free alkali. In addition, there are methods for preparing ethyl chloride, such as phosphorous oxychloride, sodium ethoxide method, ethanol alkali powder method, etc.

Uses

Diethyl Chlorothiophosphate is used in the preparation of various organophosporus insecticide including Flupyrazofos (F598620) and Chlorpyrifos (C425300).

Production

(1972) 9.1X10+8 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

100% AS A CHEM INT FOR THE INSECTICIDE PARATHION (1975)

Phosphorochloridothioic acid, O,O-diethyl ester: ACTIVE|T - indicates a substance that is the subject of a final TSCA section 4 test rule.

GAS CHROMATOGRAPHIC DETERMINATION OF HYMEXAZOLE (HYDROXY ISOZAZOLE) RESIDUES IN PLANTS & SOIL WITH PHOSPHORUS SENSITIVE DETECTORS. METHOD BASED ON DERIVATIZATION OF HYMEXAZOL TO DIETHYL THIOPHOSPHATE. THIO PHOSPHORYLATION TECHNIQUE REPORTED FOR RESIDUE ANALYSIS OF PHENOLIC COMPD FORMED FROM CARBAMATE INSECTICIDES, WITH DIMETHYL CHLOROTHIOPHOSPHATE BEING REACTED IN DRY BENZENE WITH PYRIDINE PRESENT.|DETERMINATION IN AIR BY GAS CHROMATOGRAPHY USING FLAME PHOTOMETRIC DETECTOR SPECIFIC FOR PHOSPHORUS. PROCEDURE TESTED FOR CONCN BETWEEN 0.1 & 2 PPM, WITH POSSIBLE MINIMAL DETECTION OF ORGANOPHOSPHATES AT 0.01 PPM (0.1 NG).

Health Hazards -> Corrosives

Computed Properties

Molecular Weight:188.61
XLogP3:2.7
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:187.9827654
Monoisotopic Mass:187.9827654
Topological Polar Surface Area:50.6
Heavy Atom Count:9
Complexity:109
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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