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Basic Information

Molecular Structure:
CAS No.:	2921-88-2
Name:	Chlorpyrifos
Article Data:	21

Formula:	C₉H₁₁Cl₃NO₃PS
Molecular Weight:	350.59
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;
EINECS:	220-864-4
Density:	1.48 g/cm³
Melting Point:	42-44 °C
Boiling Point:	375.9 °C at 760 mmHg
Flash Point:	181.1 °C
Solubility:	Insoluble in water
Appearance:	White granular crystals
Hazard Symbols:	T,N
Risk Codes:	25-50/53-36-20/21/22-11-38
Safety:	1/2-45-60-61-36/37-26
Transport Information:	UN 2783
PSA:	82.48000
LogP:	5.36870

Synthetic route

: 2524-04-1
diethyl phosphorochloridothioate

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

: 2921-88-2
Chlorpyrifos

Conditions

Conditions	Yield
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

Conditions	Yield
With dmap; potassium hydroxide In dichloromethane; water

...Expand

: 2921-88-2
Chlorpyrifos

: 6515-38-4
3,5,6-trichloropyridin-2 ol

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium iodide In acetone at 45℃; for 5h;	90%

: 2921-88-2
Chlorpyrifos

: 5598-15-2
chlopyrifos oxon

Conditions

Conditions	Yield
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

Conditions	Yield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;	41.95%

: 2921-88-2
Chlorpyrifos

: 7646-85-7
zinc(II) chloride

: C9H11Cl3NO3PSZn(2+)

Conditions

Conditions	Yield
In methanol at 110℃; for 48h; Autoclave; Green chemistry;	26.19%

: 2921-88-2
Chlorpyrifos

: cobalt(II) chloride hexahydrate

: C9H11Cl3CoNO3PS(2+)

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

Raw Materials

Downstream Products

762-04-9

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Chemistry

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

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.

Uses

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

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.

Safety Profile

Hazard Symbols: Toxic T; Dangerous N
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.

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 .