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

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

Uses

Used in Pesticide Industry:
Diethyl chlorothiophosphate is used as an intermediate in the preparation of various organophosphorus insecticides, such as Flupyrazofos (F598620) and Chlorpyrifos (C425300). These insecticides are effective in controlling pests and protecting crops.
Used in Oil and Gasoline Industry:
Diethyl chlorothiophosphate is used as an additive in oil and gasoline to enhance their performance and efficiency.
Used in Flame Retardant Industry:
Diethyl chlorothiophosphate is also used as a flame retardant, helping to reduce the risk of fire and improve the safety of various materials and products.

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

• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 2901-90-8 bis(diethoxyphosphoryl)disulphide 
• 1639-18-5 diethoxythioxaphosphoranesulfenyl chloride 
• 762-04-9 phosphonic acid diethyl ester 
• 589-57-1 diethyl phosphorylchloridite 
• 110-86-1 pyridine 
• 64-17-5 ethanol 
• 56-23-5 tetrachloromethane 
• 37984-79-5 μ-tetrasulfido-1,2-dithio-diphosphoric acid tetra-O-ethyl ester 
• 6926-73-4 bis(diethoxyphosphinothioyl)trisulfide 
• 7782-50-5 chlorine 
• 2465-65-8 O,O'-diethyl thiophosphoric acid 
• 4403-51-4 bis(diethylphosphoryl)disulfide 
• 19171-57-4 dichlorotriphenyl-λ⁴-phosphane 

Downstream Products

• 107-49-3 Tetraethyl pyrophosphate 
• 645-78-3 tetraethyl thiopyrophosphate 
• 3689-24-5 sulfotep 
• 117881-35-3 O,O-diethyl-phthalimido phosphorothioate 
• 299-45-6 potasan 
• 109161-68-4 O,O-diethyl-O-(4-methyl-6-coumarino)-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 
• 56-72-4 coumaphos 
• 96776-74-8 thiophosphoric acid O-(4-chloro-6-oxo-1-phenyl-1,6-dihydro-pyridazin-3-yl) ester O',O''-diethyl ester 
• 92297-95-5 thiophosphoric acid O-(5-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 
• 64965-21-5 3-chloro-1-ethyl-1H-quinolin-4-one 

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.

Diazinon hapten and artificial antigen, preparation method and application thereof

The invention relates to a diazinon hapten and an artificial antigen, a preparation method and application thereof. The preparation method comprises the following steps of: taking thiophosphoryl chloride as an initiator, reacting thiophosphoryl chloride with ethanol in an alkaline environment, and then carrying out reactione with (2-isopropyl-6-oxo-1, 6-dihydro-4-pyrimidinyl)acetic acid to obtaina compound containing a carboxyl group, namely a diazinon hapten; and coupling the hapten with a carrier protein to obtain the artificial antigen. Animals immunized by using the artificial antigen cangenerate specific antibodies aiming at diazinon, and the specific antibodies can be used for establishing an enzyme-linked immunosorbent assay method of diazinon and a colloidal gold test strip rapiddetection method, so that residues of diazinon in vegetables and fruits can be rapidly detected.

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.

Synthesis method of O, O-dialkyl thiphosphoryl chloride

The invention discloses a synthesis method of O, O-diakyl thiphosphoryl chloride. In a reaction system where O, O-dialkyl S-hydro-phophorodithioate and chlorine are subjected to a chlorination reaction to prepare O, O-dialkyl thiphosphoryl chloride, an excess chlorine is introduced to make sulphur generated in the reaction be converted into disulfur dichloride, and disulfur dichloride is convertedinto sulfur dichloride afterwards; and by controlling the reaction temperature and arranging the reaction system to be in the negative pressure state, sulfur dichloride is moved out of the reaction system in the reaction process through distillation and condensing. The synthesis method substantially achieves the atomic economy based on a green chemistry concept; the overall cost of raw materialsis far lower than that in a traditional method, the amount of the three wastes is less, and the three wastes are easy to dispose; a traditional solid-liquid separation step is cancelled, automated production is facilitated, and meanwhile, improvement of the safety and environment production level of the device is facilitated; and O, O-dialkyl thiphosphoryl chloride is not in contact with water, disintegration of the product is avoided, the yield rate is as high as 93%, and the product content can reach 99%.

Production method for O,O-dialkyl thiophosphoryl chloride

The invention relates to a production method for O,O-dialkyl thiophosphoryl chloride, and belongs to the field of manufacturing of O,O-dialkyl thiophosphoryl chloride through a chemical method. Raw materials comprise dialkyl phosphite, sulfur or sulfide, chlorine or a chlorinating agent and the like. The production method comprises the steps: carrying out a reaction of dialkyl phosphite and sulfur or sulfide in a synthesis kettle for 2 hours, then chloridizing by chlorine or the chlorinating agent to obtain an O,O-dialkyl thiophosphoryl chloride crude product, and then washing with water to obtain the product O,O-dialkyl thiophosphoryl chloride. The total yield can reach 98%-99%, the content of O,O-dialkyl thiophosphoryl chloride can reach more than or equal to 99.5%, the product quality is good, and the purity of the product can reach 99-99.9%; and the production method has the advantages of simple production process, safe production, low energy consumption, and no pollution. The problems in the prior art that a large amount of alcohol is needed to be recycled, consumption of steam is high and energy consumption is high are solved; and the problems that all the process routes need freezing, a large amount of freezing energy and circulating water is needed and the electric energy consumption is high are solved.

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.

Organophosphorus hapten, wide-spectrum polyspecific antigen, antibody and preparation method and application of hapten, antigen and antibody

The invention discloses an organophosphorus hapten, a wide-spectrum polyspecific antigen, an antibody and a preparation method and application of the hapten, the antigen and the antibody. The technical defect of an existing organophosphorus pesticide residue immunity analysis method is overcome, the organophosphorus wide-spectrum polyspecific immunity analysis concept is provided, and for organophosphorus pesticides, the method is good in accuracy and sensitivity, can be used for detecting organophosphorus in agricultural products and food samples, realizes universal wide-spectrum polyspecific detection and is quite convenient and rapid to implement in actual use. The wide-spectrum polyspecific antigen has the structure shown in the formula (III) (the formula is shown in the description).

Synthetic method of methyl phosphite and glufosinate-ammonium

The invention discloses a synthetic method of methyl phosphite and glufosinate-ammonium. The method comprises the steps: with phosphorus pentasulfide as a starting material, then carrying out vulcanization reaction, chlorination reaction, water washing and distillation purification, then carrying out catalytic hydrogenation to obtain chloride phosphite (III), and next carrying out Grignard reaction to obtain methyl phosphite (IV), wherein R is C1-C4 alkyl. The method comprises the steps: with phosphorus pentasulfide as the starting material, then carrying out vulcanization reaction, chlorination reaction, water washing and distillation purification, then carrying out catalytic hydrogenation to obtain chloride phosphite, next carrying out Grignard reaction to synthesize methyl phosphite (IV), and thus obtaining the final product glufosinate-ammonium through a Strecker route of the prior art. The synthetic yield is increased, methyl phosphorus dichloride and other unstable corrosive intermediates cannot be produced, the discharge of three-waste substances is reduced, and environment-friendly costs and pressure are reduced.

O, O-dialkyl thiophosphoryl chloride drog-free preparation method

The invention discloses a waste residue-free preparation method of O,O-dialkyl thiophosphoryl chloride, which is characterized by comprising the following steps: by taking dialkyl chlorophosphite as an intermediate, performing chlorination with O,O-dialkyl phosphorodithioate under the effect of strong Lewis acid metal chloride to prepare O,O-dialkyl thiophosphoryl chloride with the structural general formula shown in the specification, wherein the chemical equation is shown in the specification. The method for preparing high-content O,O-dialkyl thiophosphoryl chloride, disclosed by the invention, has the advantages of simple process route, mild reaction conditions, simple after-treatment and low production cost, and is convenient for industrial transformation; and the method avoids or reduces pollution, strictly controls the process, saves after-treatment and prevents the generation of viscose waste sulfur residues.

Design and synthesis of novel active phosphonate esters and their application in preparation of ceftriaxone

For a series of active phosphonate esters, the anhydride abbreviated as ANPTA (6a) exhibits the highest reactivity in the preparation of ceftriaxone. The synthesis of ceftriaxone was optimized with the pilot-scale yield reaching 95.7%. The results were explained from the structural viewpoint and supported by analysis of the calculated Mulliken atomic charge distribution.