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Diethyl chlorophosphate is a phosphorous halide that is primarily used for biochemical research and as an intermediate in organic synthesis.

814-49-3 Suppliers

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  • 814-49-3 Structure
  • Basic information

    1. Product Name: Diethyl chlorophosphate
    2. Synonyms: Diethoxy chlorophosphate;Phosphoric acid chloride diethyl ester;Chloridophosphoric acid diethyl;Chloridophosphoric acid diethyl ester;Chlorophosphonic acid diethyl;Chlorophosphonic acid diethyl ester;Chlorophosphonic acid O,O-diethyl ester;Diethyl phosphoric chloride
    3. CAS NO:814-49-3
    4. Molecular Formula: C4H10ClO3P
    5. Molecular Weight: 172.55
    6. EINECS: 212-396-4
    7. Product Categories: Pharmaceutical Intermediates;Phosphorus compounds;Miscellaneous Reagents
    8. Mol File: 814-49-3.mol
  • Chemical Properties

    1. Melting Point: 95-96 °C
    2. Boiling Point: 60 °C2 mm Hg(lit.)
    3. Flash Point: 142 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 1.194 g/mL at 25 °C(lit.)
    6. Vapor Density: 5.94 (vs air)
    7. Vapor Pressure: 0.1 mm Hg ( 25 °C)
    8. Refractive Index: n20/D 1.416(lit.)
    9. Storage Temp.: 2-8°C
    10. Solubility: N/A
    11. Water Solubility: Soluble in alcohol and chloroform. Slightly soluble in water.
    12. Sensitive: Moisture Sensitive
    13. BRN: 471433
    14. CAS DataBase Reference: Diethyl chlorophosphate(CAS DataBase Reference)
    15. NIST Chemistry Reference: Diethyl chlorophosphate(814-49-3)
    16. EPA Substance Registry System: Diethyl chlorophosphate(814-49-3)
  • Safety Data

    1. Hazard Codes: T+
    2. Statements: 23-27/28-33-26/27/28-34
    3. Safety Statements: 26-36/37/39-45-38-28A-7/9-28
    4. RIDADR: UN 2927 6.1/PG 1
    5. WGK Germany: 3
    6. RTECS: TD1400000
    7. F: 10-19-21
    8. TSCA: Yes
    9. HazardClass: 6.1(a)
    10. PackingGroup: II
    11. Hazardous Substances Data: 814-49-3(Hazardous Substances Data)

814-49-3 Usage

Uses

Used in Biochemical Research:
Diethyl chlorophosphate is used as a biochemical research agent for studying the properties and interactions of phosphorous compounds in biological systems.
Used in Organic Synthesis:
Diethyl chlorophosphate is used as an intermediate in organic synthesis for the production of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and versatility make it a valuable component in the synthesis of a wide range of molecules.

Reactivity Profile

Organophosphates, such as Diethyl chlorophosphate, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

Diethyl chlorophosphate is a cholinesterase inhibitor. It has high oral and very high dermal toxicity. It is a skin irritant. It is also toxic by inhalation.

Fire Hazard

Emits very toxic fumes of chloride and phosphorus oxides when heated to decomposition.

Safety Profile

Deadly poison by skin contact. Poison by ingestion. A cholinesterase inhibitor. See also PARATHION. Trace HCl catalyzes a hazardous reaction during the preparation of diethyl phosphate from diethyl chlorophosphate. When heated to decomposition it emits very toxic fumes of Cl and POx.

Check Digit Verification of cas no

The CAS Registry Mumber 814-49-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,1 and 4 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 814-49:
(5*8)+(4*1)+(3*4)+(2*4)+(1*9)=73
73 % 10 = 3
So 814-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H10ClO3P/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3

814-49-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl chlorophosphate

1.2 Other means of identification

Product number -
Other names 1-[chloro(ethoxy)phosphoryl]oxyethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:814-49-3 SDS

814-49-3Relevant articles and documents

The synthesis and reactions of dialkyl fluoroalkyl phosphates

Timperley, Christopher M.,Morton, Ian J.,Waters, Matthew J.,Yarwood, Jason L.

, p. 95 - 100 (1999)

Dimethyl and diethyl fluoroalkyl phosphates were prepared from (1) a dialkyl phosphite with a fluoroalcohol, triethylamine and carbon tetrachloride, (2) a dialkyl chlorophosphate with a fluoroalcohol and triethylamine, and (3) a dialkyl chlorophosphate with the sodium salt of a fluoroalcohol. Dimethyl and diethyl (2,2,2-trifluoroethyl) phosphates reacted with bromotrimethylsilane (TMSBr) in chloroform to give two products with loss of alkyl bromide. The major product was an alkyl (trifluoroethyl) trimethylsilyl phosphate, RO(TMSO)P(O)OCH2CF3 and the minor product was a bis(trimethylsilyl) trifluoroethyl phosphate, (TMSO)2P(O)OCH2CF3. The mechanism presumably involves initial attack of an alkoxy oxygen atom on the silicon atom of bromotrimethylsilane. Diethyl (2,2,2-trifluoroethyl) phosphate is resistant to chlorination. It did not react with oxalyl or thionyl chloride in chloroform under prolonged reflux. Unlike triethyl phosphate, it did not react with phosphorus oxychloride in chloroform under reflux.

Extraction of hexachloroplatinate from hydrochloric acid solutions with phosphorylated hexane-1,6-diyl polymers

Hahn, Simone,Holdt, Hans-Jürgen

, p. 878 - 888 (2012)

A series of diols (diethylene glycol, triethylene glycol, butane-1,4-diol and hexane-1,6-diol) were immobilized onto Merrifield resin and subsequently phosphorylated with dialkyl chlorophosphate (alkyl = Me, Et, Bu). The resins bearing hexane-1,6-diyl groups exhibited very good extraction abilities in regard to precious metal chloro complexes like platinum(IV), palladium(II) and rhodium(III). In batch experiments, more than 98% of Pt(IV) is extracted even when the metal and the hydrochloric acid concentration is enhanced significantly. Elution can be achieved with a solution of 0.5 mol L-1 thiourea in 0.1 mol L-1 hydrochloric acid. In the presence of other noble metals, platinum(IV) is preferentially bound. The extraction yield decreases in slightly acidic solution in the following order: Pt(IV) ≈ Pd(II) > Rh(III) and changes with increasing hydrochloric acid concentration to Pt(IV) > Pd(II) ? Rh(III). At different ratios of metal and acid, the temperature has nearly no influence on the platinum extraction. On slightly acidic media, the extraction of rhodium decreases by 30% when the temperature is increased from 10°C to 40°C. When the acid and metal concentration is enhanced, the palladium extraction decreases by 7-9%, depending on the resin.

Organophosphorus derivatives containing piperazine dithiosemicarbazones as chemotherapeutants against fungal pathogens of sugarcane

Chandra, Ruchi,Pandey,Sengupta

, p. 2181 - 2184 (2005)

Five novel organophosphorus derivatives have been synthesized by the reactions of O,O-diethylchlorophosphate with piperazine dithiosemicarbazones. The derivatives have been characterized on the basis of analyses and spectral (IR, 1H NMR) data. Fungicidal activities of these derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescence have been evaluated. The screening results have been correlated with the structural features of the tested compounds. Organophosphorus derivatives containing 1,4-bis(4-chlorobenzaldehyde)piperazine dithiosemicarbazone and 1,4-bis(4-methoxybenzaldehyde)piperazine dithiosemicarbazone proved to be more active than some prevalent commercial synthetic fungicides.

Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines

Bao, Ming,He, Min,Wang, Yi,Yu, Xiaoqiang

, p. 14720 - 14731 (2021/11/16)

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).

Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes

Rohde, Laurence N.,Wild, Thérèse H.,Diver, Steven T.

, p. 1371 - 1384 (2021/02/05)

A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields. The resulting dienes were further transformed by Horner-type Wittig reactions and a Diels-Alder cycloaddition.

Quinoline derivatives, and preparation method and use thereof

-

Paragraph 0232-0234, (2019/10/17)

The invention belongs to the technical field of insecticides and acaricides, and particularly relates to quinoline derivatives, and a preparation method and a use thereof, and concretely provides compounds represented by formula (I), and stereoisomers, racemates, tautomers, isotope labels, oxynitrides, pharmaceutically acceptable salts or solvates thereof. The compounds of the formula (I) have an excellent activity against various pests and pest mites in the agricultural field or other fields. The compounds can achieve an excellent control effect at a very low dosage, so the compounds can be used to prepare insecticides and/or acaricides. In addition, the preparation steps of the compounds of the invention are simple, and the product yield is high, so that the compounds have a good application prospect.

Phosphate ionic liquids as well as synthetic method and application thereof

-

Paragraph 0027; 0028, (2018/05/16)

The invention discloses phosphate ionic liquids, a synthetic method thereof and an application as a lithium extraction agent. According to the method, the functional ionic liquids containing phosphamide groups are prepared from dibutyl phosphite, trichloroisocyanuric acid, N,N'-dimethylethanediamine and potassium hexafluorophosphate taken as raw materials through phosphoryl chlorination reaction,amidation with amine, salt forming reaction and exchange reaction. Compared with the prior art, the ionic liquids and the synthetic method thereof have the characteristics that operation is simple, industrial popularization and application are facilitated and the like, and have important application values.

Eco-Friendly and Industrially Scalable Synthesis of the Sex Pheromone of Lobesia botrana. Important Progress for the Eco-Protection of Vineyard

Cahiez, Gérard,Guerret, Olivier,Moyeux, Alban,Dufour, Samuel,Lefevre, Nicolas

supporting information, p. 1542 - 1546 (2017/10/25)

A one-pot synthesis of the pheromone of Lobesia botrana is described. The procedure allows an efficient and economical access to this product which is used for the protection of vineyards.

A single-step one pot synthesis of O,O′-dialkyl N,N-dialkylphosphoramidates from dialkylphosphites

Purohit, Ajay Kumar,Pardasani, Deepak,Kumar, Ajeet,Goud, D. Raghavender,Jain, Rajiv,Dubey

, p. 3754 - 3756 (2016/07/26)

An efficient synthetic method has been developed to obtain chemical weapons convention (CWC)-related O,O′-dialkyl-N,N-dialkylphosphoramidates from dialkylphosphites using inorganic reagents (CuCl2and Cs2CO3) at room temperature.

New benzotriazole-based reagents for the phosphonylation of various N-, O-, and S-nucleophiles

Panmand, Deepak S.,Tiwari, Anand D.,Panda, Siva S.,Monbaliu, Jean-Christophe M.,Beagle, Lucas K.,Asiri, Abdullah M.,Stevens, Christian V.,Steel, Peter J.,Hall, C. Dennis,Katritzky, Alan R.

supporting information, p. 5898 - 5901 (2015/01/08)

Benzotriazole surrogates showing higher stabilities than the corresponding chlorophosphates, allow phosphonylation of a variety of N-, O-, and S-nucleophiles in good yields.