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Chlorpyrifos

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Name

Chlorpyrifos

EINECS 220-864-4
CAS No. 2921-88-2 Density 1.48 g/cm3
PSA 82.48000 LogP 5.36870
Solubility Insoluble in water Melting Point 42-44 °C
Formula C9H11Cl3NO3PS Boiling Point 375.9 °C at 760 mmHg
Molecular Weight 350.59 Flash Point 181.1 °C
Transport Information UN 2783 Appearance White granular crystals
Safety 1/2-45-60-61-36/37-26 Risk Codes 25-50/53-36-20/21/22-11-38
Molecular Structure Molecular Structure of 2921-88-2 (Chlorpyrifos) Hazard Symbols ToxicT,DangerousN
Synonyms

Clorpyrifos;Bonidel;Chlora;Chloroban;Chloropyrifos-ethyl;O,O-Diethyl O-(3,5,6-trichloro-2-pyridinyl)phosphorothioate;Pyrinex;Radar (fungicide);Spannit;Tafaban;Terial 40L;XRM 5160;suSCon Plus;Chlorpyrifos E;Chlorpyriphos;Clorpirifos;Danusban;Dhanusban;Durmet;Dursban;Dursban TC;Dursband 48;Empire 20;Ethyl chlorpyriphos;Geodinfos;Grofo;Lentrek;Lorsban;Lorsban 50SL;

Article Data 21

Chlorpyrifos Synthetic route

2524-04-1

diethyl phosphorochloridothioate

sodium salt of 3,5,6-trichloropyridine-2-ol

2921-88-2

Chlorpyrifos

Conditions
ConditionsYield
With dmap; N-benzyl-N,N,N-triethylammonium chloride; sodium dodecyl sulfate; potassium carbonate In water at 50℃; for 2.5h; pH=9.5 - 10; Reagent/catalyst; Temperature; Time; pH-value;97.5%
With dmap; N-benzyl-N,N,N-triethylammonium chloride; boric acid; sodium chloride; sodium hydroxide In dichloromethane; water at 40℃; for 0.25h; pH=9.9; Reagent/catalyst; Solvent; Temperature;92%
With dmap; N-benzyl-N,N,N-triethylammonium chloride; sodium hydrogencarbonate; sodium carbonate; sodium 4-dodecylbenzenesulfonate In methyl cyclohexane at 50℃; for 1h;
2402-79-1

2,3,5,6-tetrachloropyridine

25108-36-5

potassium picolinate

2524-04-1

diethyl phosphorochloridothioate

2921-88-2

Chlorpyrifos

Conditions
ConditionsYield
With dmap; potassium hydroxide In dichloromethane; water
2921-88-2

Chlorpyrifos

6515-38-4

3,5,6-trichloropyridin-2 ol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 4h; Heating;91.7%
With potassium hydroxide In ethanol for 1h; Heating;90%
With water at 40℃; for 960h; Rate constant; Thermodynamic data; E(a); other natural water, pH = 8.0;
2921-88-2

Chlorpyrifos

O-ethyl O-(3,5,6-trichloropyridin-2-yl)-O-hydrogenphosphorothioate

Conditions
ConditionsYield
With sodium iodide In acetone at 45℃; for 5h;90%
2921-88-2

Chlorpyrifos

5598-15-2

chlopyrifos oxon

Conditions
ConditionsYield
With dihydrogen peroxide In acetic acid for 3h; Irradiation;80%
With rat liver microsomes Enzyme kinetics; Further Variations:; Reaction partners; desulfuration; Enzymatic reaction;
With bromine In acetonitrile
2921-88-2

Chlorpyrifos

copper(II) choride dihydrate

C9H11Cl3CuNO3PS(2+)

Conditions
ConditionsYield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;41.95%
2921-88-2

Chlorpyrifos

7646-85-7

zinc(II) chloride

C9H11Cl3NO3PSZn(2+)

Conditions
ConditionsYield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;26.19%
2921-88-2

Chlorpyrifos

cobalt(II) chloride hexahydrate

C9H11Cl3CoNO3PS(2+)

Conditions
ConditionsYield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;19.02%
2921-88-2

Chlorpyrifos

17689-17-7

6-mercaptocaproic acid

6-[3,5-Dichloro-6-(diethoxy-thiophosphoryloxy)-pyridin-2-ylsulfanyl]-hexanoic acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 1h; Heating;17%
With potassium hydroxide 1.) EtOH, reflux, 2.) EtOH, reflux, 1 h; Yield given. Multistep reaction;
2921-88-2

Chlorpyrifos

manganese(II) chloride tetrahydrate

C9H11Cl3MnNO3PS(2+)

Conditions
ConditionsYield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;16.01%

Chlorpyrifos Chemical Properties

Molecular formula: C9H11Cl3NO3PS
Molar mass: 350.59 g/mol 
Index of Refraction: 1.565
Density: 1.48 g/cm3
Flash Point: 181.1 °C
Enthalpy of Vaporization: 59.9 kJ/mol
Boiling Point: 375.9 °C at 760 mmHg
Vapour Pressure: 1.63E-05 mmHg at 25 °C
Melting point: 42-44°C
Storage tempreture: Approx 4 °C
Water solubility: Insoluble. 0.00013 g/100 mL
Appearance: White granular crystals
Structure of Chlorpyrifos (CAS NO.2921-88-2):
                       
IUPAC Name: Diethoxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl)oxy-λ5-phosphane
Product Category of Chlorpyrifos (CAS NO.2921-88-2): Organics;Intermediates & Fine Chemicals;Pharmaceuticals;CAlphabetic;CHMethod Specific;Insecticides;Pesticides;AcaricidesAlphabetic;Organophorous

Chlorpyrifos History

First registered in 1965 and marketed by Dow Chemical Company under the tradenames Dursban and Lorsban, Chlorpyrifos (CAS NO.2921-88-2) was a well known home and garden insecticide, and at one time it was one of the most widely used household pesticides in the US. In 1995, Dow was fined $732,000 for not sending the EPA reports it had received on 249 Dursban poisoning incidents, and in 2003, Dow agreed to pay $2 million - the largest penalty ever in a pesticide case - to the state of New York, in response to a lawsuit filed by the Attorney General to end Dow's illegal advertising of Dursban as "safe". On July 31, 2007, a coalition of farmworker and advocacy groups filed a lawsuit against the EPA seeking to end agricultural use of the chlorpyrifos. The suit claims that the continued use of chlorpyrifos poses an unnecessary risk to farmworkers and their families. In August 2007, Dow's Indian offices were raided by Indian authorities for allegedly bribing officials to allow chlorpyrifos to be sold in the country. In 2008, a federal judge imposed 1000 ft buffer zones around waterways to protect endangered species including salmon. Aerial applications of chlorpyrifos will prohibited within these zones.

Chlorpyrifos Uses

 Chlorpyrifos (CAS NO.2921-88-2) is used to control insect pests as Insecticide and acaricide
 

Chlorpyrifos Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 5mg/kg (5mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
chicken LD50 oral 25400ug/kg (25.4mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Toxicology and Applied Pharmacology. Vol. 11, Pg. 49, 1967.
duck LD50 oral 76mg/kg (76mg/kg)   Toxicology and Applied Pharmacology. Vol. 20, Pg. 57, 1971.
guinea pig LD50 oral 504mg/kg (504mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C74, 1991.
guinea pig LDLo subcutaneous 100mg/kg (100mg/kg)   Journal of Economic Entomology. Vol. 60, Pg. 733, 1967.
mammal (species unspecified) LD50 unreported 163mg/kg (163mg/kg)   Journal of Agricultural and Food Chemistry. Vol. 27, Pg. 712, 1979.
man TDLo oral 300mg/kg (300mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS
BEHAVIORAL: MUSCLE WEAKNESS
BEHAVIORAL: COMA
Archives of Toxicology. Vol. 59, Pg. 176, 1986.
mouse LD50 intraperitoneal 192mg/kg (192mg/kg)   Toxicology and Applied Pharmacology. Vol. 65, Pg. 144, 1982.
mouse LD50 oral 60mg/kg (60mg/kg)   Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 13, Pg. 11, 1978.
mouse LD50 skin 120mg/kg (120mg/kg)   Yakkyoku. Pharmacy. Vol. 38, Pg. 745, 1987.
pigeon LD50 oral 10mg/kg (10mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
quail LD50 oral 13300ug/kg (13.3mg/kg)   ASTM Special Technical Publication. Vol. (680), Pg. 157, 1979.
rabbit LD50 oral 1gm/kg (1000mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 45, 1978.
rabbit LD50 skin 2gm/kg (2000mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 203, 1973.
rat LC50 inhalation > 200mg/m3/4H (200mg/m3)   Pesticide Manual. Vol. 9, Pg. 166, 1991.
rat LD50 oral 82mg/kg (82mg/kg)   Toxicology and Applied Pharmacology. Vol. 14, Pg. 515, 1969.
rat LD50 skin 202mg/kg (202mg/kg)   Toxicology and Applied Pharmacology. Vol. 14, Pg. 515, 1969.
rat LD50 unreported 150mg/kg (150mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 339, 1971.

Chlorpyrifos Safety Profile

Hazard Symbols: ToxicT;Dangerous
Risk Codes: R25;R50/53
R25 :Toxic if swallowed. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.  
Safety Description: S1/2;S45;S60;S61
S1/2:Keep locked up and out of the reach of children. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.

Chlorpyrifos Specification

 Chlorpyrifos , its cas register number is 2921-88-2. It also can be called O,O-Diethyl O-3,5,6-trichloro-2-pyridyl phosphorothioate ; Phosphorothioic acid O,O-diethyl O-(3,5,6-trichloro-2-pyridinyl) ester ; Chlorpyrifos-ethyl ; Chlorpyritos ; Clorpyrifos ; Dursban HF ; Eradex ; Lorsban 4E-SG ; Pyrinex ; Super I.Q.A.P.T. ; Trichlorpyrphos ; and Dowco 179 .

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