2524-04-1

Basic information

• Product Name: Diethyl chlorothiophosphate
• Synonyms: Diethoxythiophosphoryl chloride;diethoxythiophosphorylchloride;Diethyl phosphorochloridothioate;Diethyl phosphorothiochloridate;Diethyl phosphorothionochloridate;Diethyl thiophosphoric chloride;Diethylchlorthiofosfat;diethylchlorthiofosfat(czech)
• CAS NO: 2524-04-1
• Molecular Formula: C₄H₁₀ClO₂PS
• Molecular Weight: 188.61
• EINECS: 219-755-4
• Product Categories: Pharmaceutical Intermediates;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Phosphorylating and Phosphorothioating Agents;Protecting Agents, Phosphorylating Agents & Condensing Agents;Miscellaneous Reagents, Sulfur & Selenium Compounds
• Mol File: 2524-04-1.mol
• Article Data: 28

Chemical Properties

• Melting Point: -75℃
• Boiling Point: 96 °C
• Flash Point: >230 °F
• Appearance: /liquid
• Density: 1.2 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.4 mm Hg ( 50 °C)
• Refractive Index: n20/D 1.472(lit.)
• Water Solubility: hydrolyzes, immiscible
• CAS DataBase Reference: Diethyl chlorothiophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl chlorothiophosphate(2524-04-1)
• EPA Substance Registry System: Diethyl chlorothiophosphate(2524-04-1)

Safety Data

• Hazard Codes: T,T+
• Statements: 23/24/25-34-26-21/22
• Safety Statements: 23-26-36/37/39-45-28A
• RIDADR: UN 2751 8/PG 2
• WGK Germany: 3
• RTECS: TD1780000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 2524-04-1(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLORLESS TO LIGHT YELLOW LIQUID

Uses

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

General Description

A colorless to light amber liquid with a disagreeable odor. Density 1.196 g / cm3. Boiling point 120°F.Flash point below 100°F. 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.

Air & Water Reactions

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.

Reactivity Profile

Diethyl chlorothiophosphate 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].

Health Hazard

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.

Fire Hazard

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. 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.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C4H10ClO2PS/c1-3-7-8(5,6)9-4-2/h3-4H2,1-2H3

Upstream product

• 1498-64-2 O-ethyl dichlorothiophosphate 
• 64-17-5 ethanol 
• 2414-98-4 magnesium ethylate 
• 594-71-8 2-chloro-2-nitro-propane 
• 71774-85-1 potassium diethyl thiophoshite 
• 1186-08-9 diethoxyoxophosphoranesulfenyl chloride 
• 65007-83-2 2-(neopentyloxy)benzo-1,3,2-dioxaphosphole 
• 7782-50-5 chlorine 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 762-04-9 phosphonic acid diethyl ester 
• 589-57-1 diethyl phosphorylchloridite 
• 110-86-1 pyridine 
• 56-23-5 tetrachloromethane 
• 37984-79-5 μ-tetrasulfido-1,2-dithio-diphosphoric acid tetra-O-ethyl ester 

Downstream Products

• 107-49-3 Tetraethyl pyrophosphate 
• 645-78-3 tetraethyl thiopyrophosphate 
• 3689-24-5 sulfotep 
• 117881-35-3 O,O-diethyl-phthalimido phosphorothioate 
• 93897-79-1 thiophosphoric acid O,O'-diethyl ester O''-(6-oxo-5-phenyl-1,6-dihydro-pyridazin-3-yl) ester 
• 92439-86-6 thiophosphoric acid O,O'-diethyl ester O''-(6-oxo-4-phenyl-1,6-dihydro-pyridazin-3-yl) ester 
• 96776-74-8 thiophosphoric acid O-(4-chloro-6-oxo-1-phenyl-1,6-dihydro-pyridazin-3-yl) ester O',O''-diethyl ester 
• 572-48-5 3-diethoxythiophosphoryloxy-7,8,9,10-tetrahydro-benzo[c]chromen-6-one 
• 109222-16-4 4,5,6,7-tetrachloro-2-diethoxythiophosphoryloxy-isoindoline-1,3-dione 
• 16604-76-5 thiophosphoric acid S-ethyl ester-O,O'-bis-(4-nitro-phenyl ester) 
• 56-38-2 parathion 
• 18264-33-0 thiophosphoric acid O,O'-diethyl ester-O''-(3-chloro-phenyl ester) 
• 108130-72-9 O-trichloroacetyl-thiophosphoric acid O',O''-diethyl ester 
• 126-68-1 O,O,O-triethyl phosphorothioate 

Relevant articles and documents

Distribution and elimination of 14C-ethion insecticide in chamomile flowers and oil

The residual fate of 14C-ethion labeled at the ethyl group in chamomile flowers and oil was studied. 14C-ethion and some of its degradation products have been prepared for the present investigation. 14C-residues in its flowers and oil were determined at different time intervals. Chromatographic analysis of chamomile oil extracts revealed the presence of the parent compound together with four metabolites, which were identified as ethion monooxon, ethion dioxon, O,O-diethyl phosphorothioate, and O-ethyl phosphorothioate. Effect of drying on ethion residues in chamomile flowers was investigated. Ethion residues were decreased by sun drying of chamomile flowers. The percentage of removal was 18%-47%. Effect of using low cost adsorbents for removal of ethion residues from chamomile oil was investigated. The removal percentage due to adsorption was 100% for CaO and saw dust adsorbers and for watermelon peels, bagass, and rice bran adsorbers were 36%, 41%, and 90%, respectively. Our results proved that the addition of CaO saw dust and rice bran reduced the pesticide residues, so we recommend the addition of these adsorbents during the extraction process to reduce the risk of pesticide residues on chamomile oil. Copyright Taylor & Francis Group, LLC.

EFFECTS OF SUBSTITUENTS IN REACTIONS OF SULFENYL CHLORIDES WITH DERIVATIVES OF PHOSPHONALLENIC ACIDS

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Green synthesis technology of O,O-diethyl thiophosphoryl chloride

The invention provides a green synthesis technology of O,O-diethyl thiophosphoryl chloride and relates to the field of chemical synthesis. The green synthesis technology comprises the following steps:taking O,O-diethyl dithiophosphate to react with chlorine gas at low temperature, so as to obtain a crude product of the O,O-diethyl thiophosphoryl chloride; then transferring the crude product to react at high temperature; enabling the residual O,O-diethyl dithiophosphate to further completely react with the chlorine gas. Meanwhile, in a high-temperature reaction process, a polymeric compound isprevented from being generated when a compound catalyst is used and sulfur monochloride impurities are completely removed through reaction, so that a byproduct sulfur has a crystalline state and a product more easily separated and purified. Moreover, HCl and sulfur-containing odorous gas are pumped away through applying negative pressure and the tail gas is absorbed to prevent air pollution. In awhole reaction process, technological water does not need to be added, so that wastewater is not generated and the treatment cost of sulfur-containing and phosphorus-containing wastewater is reduced.The technology has the advantages of simplicity in operation, easiness for obtaining raw materials, moderate reaction conditions, small pollution and environment friendliness.

O,O-diethyl chlorothiophosphate and preparation method thereof

The invention discloses an O,O-diethyl chlorothiophosphate and a preparation method thereof, belonging to the technical field of insecticides. The preparation method comprises the following steps: mixing and stirring phosphorus pentasulfide and O,O-diethyl dithiophosphate, dripping a mixture of absolute ethyl alcohol and a catalyst A, preserving heat for 10 to 50min, and then filtering to obtain O,O-diethyl dithiophosphate, wherein the catalyst A is prepared from at least one of triethylamine, pyridine, ethylenediamine and carbonate; stirring the O,O-diethyl dithiophosphate at 30 to 50 DEG C, and introducing chlorine to obtain an intermediate product; heating the intermediate product to 80 to 100 DEG C, adding water, performing stirring reaction for 1 to 3h, then performing suction filtration, and enabling filtrate to stand, thus layering to obtain an oil phase and a water phase; dehydrating the oil phase, then evaporating, and collecting a fraction. The preparation method is capable of avoiding side reaction and reducing a reaction residue amount. In addition, the invention provides the O,O-diethyl chlorothiophosphate prepared by using the method.