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Parathion

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Name

Parathion

EINECS 200-271-7
CAS No. 56-38-2 Density 1.326 g/cm3
PSA 115.41000 LogP 4.44490
Solubility Slightly soluble Melting Point 6.1 ºC
Formula C10H14NO5PS Boiling Point 375 °C at 760 mmHg
Molecular Weight 291.265 Flash Point 173.5 °C
Transport Information UN 3278 Appearance light-yellow liquid
Safety 28-36/37-45-60-61-62 Risk Codes 24-26/28-48/25-50/53-67-65-38-11
Molecular Structure Molecular Structure of 56-38-2 (Parathion) Hazard Symbols VeryT+, DangerousN, HarmfulXn, FlammableF
Synonyms

Phosphorothioicacid, O,O-diethyl O-(p-nitrophenyl) ester (6CI,8CI);AAT;AATP;Alkron;Alleron;American Cyanamid 3422;Aphamite;Aralo;BAY 1605;Bayer E-605;BladanF;DNTP;Diethyl 4-nitrophenyl phosphorothioate;Diethyl p-nitrophenylphosphorothionate;Diethyl p-nitrophenyl thionophosphate;Diethyl parathion;E605;E 605F;E 605FT20;ENT 15108;Ecatox 20;Ekatox;Ekatox 20;Ethylparathion;Etilon;Folidol;Folidol E;Folidol E-605;Folidol oil;Fosferno;Fostox;Galpar;Gearphos;Lirothion;NIUIF 100;NSC 8933;Niran;Nitrostigmine;Nourithion;O,O-Diethyl O-(4-nitrophenyl) phosphorothioate;O,O-DiethylO-(p-nitrophenyl) phosphorothioate;O,O-Diethyl O-p-nitrophenyl thiophosphate;Oleofos 20;Oleoparathene;Oleoparathion;Pacol;Paramar 50;Paraphos;Parathene;Parathion A;Parathion-ethyl;Penncap E;RB;Rhodiasol;Rhodiatox;Selephos;Super Rodiatox;Thiomex;Thiophos;Thiophos 3422;Vitrex;

Article Data 29

Parathion Synthetic route

674-82-8

4-methyleneoxetan-2-one

13889-98-0

N-acetylpiperidine

56-38-2

parathion

Conditions
ConditionsYield
In tetrahydrofuran at -5 - 0℃; for 1h;83%
100-02-7

4-nitro-phenol

2524-04-1

diethyl phosphorochloridothioate

56-38-2

parathion

Conditions
ConditionsYield
With PEG-400; aluminum oxide; sodium hydroxide; water 1.) MeOH, r.t., 30 min, 2.) r.t., 1 h;79%
With triethylamine In diethyl ether at 20℃; for 12h;68%
With copper; sodium carbonate; toluene
64-17-5

ethanol

4225-51-8

4-nitrophenyl dichlorothiophosphate

56-38-2

parathion

Conditions
ConditionsYield
With pyridine
4225-51-8

4-nitrophenyl dichlorothiophosphate

141-52-6

sodium ethanolate

56-38-2

parathion

Conditions
ConditionsYield
With ethanol
28341-54-0

4-(4-nitrophenoxy)butanoic acid

141-52-6

sodium ethanolate

56-38-2

parathion

Conditions
ConditionsYield
With trichlorothiophosphine; ethanol
28341-54-0

4-(4-nitrophenoxy)butanoic acid

2524-04-1

diethyl phosphorochloridothioate

56-38-2

parathion

Conditions
ConditionsYield
With diethylene glycol
With hexamethylenetetramine; chlorobenzene
With chlorobenzene at 120℃;
With water at 95 - 100℃;
With ethanol
2524-04-1

diethyl phosphorochloridothioate

824-78-2

4-nitrophenol sodium salt

56-38-2

parathion

Conditions
ConditionsYield
In ethanol for 1h; Heating; Yield given;
56-38-2

parathion

311-45-5

paraoxon

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In dichloromethane; acetone for 0.0833333h; Ambient temperature;100%
With 3,3-dimethyldioxirane In dichloromethane; acetone for 0.0833333h; Ambient temperature; other phosphorothioates, also with phosphine sulfides;100%
With perfluro-cis-2-n-butyl-3-n-propyloxaziridine In various solvent(s) at -30℃; for 6h;90%
110-77-0

2-(ethylsulfanyl)ethanol

56-38-2

parathion

298-03-3

demeton-O

Conditions
ConditionsYield
With sodium hydroxide In cyclohexane at 50℃; for 144h;55%
56-38-2

parathion

A

598-02-7

Diethyl phosphate

B

1754-42-3

para-nitro-phenylphosphonate diethylique

C

762-04-9

phosphonic acid diethyl ester

Conditions
ConditionsYield
With magnesium monoperoxyphthalate hexahydrate In water at 25℃; for 24h;A 28%
B 38%
C 29%

Parathion Chemical Properties

Molecule structure of Parathion (CAS NO.56-38-2):

IUPAC Name: Diethoxy-(4-nitrophenoxy)-sulfanylidene-λ5-phosphane 
Molecular Weight: 291.260621 g/mol
Molecular Formula: C10H14NO5PS 
Density: 1.326 g/cm3 
Melting Point: 6.1 °C
Boiling Point: 375 °C at 760 mmHg 
Flash Point: 173.5 °C
Index of Refraction: 1.56
Molar Refractivity: 70.99 cm3
Molar Volume: 219.5 cm3
Surface Tension: 52.7 dyne/cm 
Enthalpy of Vaporization: 59.8 kJ/mol
Vapour Pressure: 1.73E-05 mmHg at 25 °C 
Water Solubility: slightly soluble
XLogP3: 3.8
H-Bond Acceptor: 5
Rotatable Bond Count: 6
Exact Mass: 291.03303
MonoIsotopic Mass: 291.03303
Topological Polar Surface Area: 70.8
Heavy Atom Count: 18
Canonical SMILES: CCOP(=S)(OCC)OC1=CC=C(C=C1)[N+](=O)[O-]
InChI: InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3
InChIKey: LCCNCVORNKJIRZ-UHFFFAOYSA-N
EINECS: 200-271-7
Product Categories: Agro-Chemicals; INSECTICIDE

Parathion History

In the 1940s, Parathion was developed by Dr. Gerhard Schrader for the German trust IG Farben. After the war and the collapse of IG Farben due to the war crime trials, the Western allies seized the patent, and parathion was marketed worldwide under different brand names and by different companies. The most common German brand was E605 (banned in Germany after 2002); this was not a food-additive "E number" as used in the EU today. "E" stands for Entwicklungsnummer (German for "development number").

Parathion Uses

As a pesticide, Parathion (CAS NO.56-38-2) is generally applied by spraying. It is often used in cotton, rice and fruit trees. The chemical is banned for use on many food crops.

Parathion Production

 Parathion is made by diethyl dithiophosphoric acid (C2H5O)2PS2H, which is obtained by treatment of P2S5 with ethanol (methanol is used to prepare methyl parathion). Diethyl dithiophosphoric acid is chlorinated to generate diethylthiophosphoryl chloride. The diethyl dithiophosphoric acid is then treated with sodium p-nitrophenolate.
2 (C2H5O)2P(S)SH + 3 Cl2 → 2 (C2H5O)2P(S)Cl + S2Cl2 + 2 HCl
(C2H5O)2P(S)Cl + NaOC6H4NO2 → (C2H5O)2P(S)OC6H4NO2 + NaCl

Parathion Toxicity Data With Reference

1.    

mma-sat 500 µg/plate

    JTEHD6    Journal of Toxicology and Environmental Health. 16 (1985),403.
2.    

dns-hmn:fbr 10 µmol/L

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB268-647 .
3.    

orl-man TDLo:429 µg/kg/4D-I:SYS

    TXAPA9    Toxicology and Applied Pharmacology. 14 (1969),603.
4.    

orl-hmn LDLo:171 µg/kg

    CMEP**    Clinical Memoranda on Economic Poisons US Dept. HEW, Public Health Service, Communicable Disease Center,Atlanta, GA.: 1956,1.
5.    

orl-wmn TDLo:5670 µg/kg:CNS,PUL,KID

    ANYAA9    Annals of the New York Academy of Sciences. 160 (1969),383.
6.    

orl-wmn TDLo:2 mL/kg

    JTCTDW    Journal of Toxicology, Clinical Toxicology. 31 (1993),497.
7.    

orl-hmn LD50:3 mg/kg

    85JFAN    Agrochemicals Handbook ,Hartley, D., andH. Kidd, eds.,Nottingham, UK.: Royal Soc. of Chemistry,1986,A311.
8.    

skn-hmn LDLo:7143 µg/kg

    SKEZAP    Shokuhin Eiseigaku Zasshi. Journal of the Food Hygiene Society of Japan. 9 (1968),1.
9.    

itr-hmn LDLo:714 µg/kg

    SKEZAP    Shokuhin Eiseigaku Zasshi. Journal of the Food Hygiene Society of Japan. 9 (1968),1.

Parathion Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 30 ,1983,p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 30 ,1983,p. 153.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-70 ,1979. ; (feed); No Evidence: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-70 ,1979. . EPA Farm Worker Field Reentry FEREAC    Federal Register. 39 (1974),16888. . EPA Extremely Hazardous Substances List. Community Right-To-Know List. EPA Genetic Toxicology Program.

Parathion Safety Profile

Hazard Codes: VeryT+, DangerousN, HarmfulXn, FlammableF
Risk Statements: 24-26/28-48/25-50/53-67-65-38-11 
R24:Toxic in contact with skin. 
R26/28:Very toxic by inhalation and if swallowed. 
R48:Danger of serious damage to health by prolonged exposure. 
R25 :Toxic if swallowed. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R67:Vapours may cause drowsiness and dizziness. 
R65:Harmful: may cause lung damage if swallowed. 
R38:Irritating to skin. 
R11:Highly flammable.
Safety Statements: 28-36/37-45-60-61-62 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S36/37:Wear suitable protective clothing and gloves. 
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. 
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.
RIDADR: UN 3278
RTECS: TF4550000
HazardClass: 6.1(a)
PackingGroup: I
A deadly poison by all routes. Human systemic effects by ingestion: general anesthetic; pulmonary effects; and kidney, ureter, bladder effects, true cholinesterase changes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. A cholinesterase inhibitor. Parathion, like the other organic phosphorus poisons, acts as an irreversible inhibitor of the enzyme cholinesterase and thus allows the accumulation of large amounts of acetylcholine. When a critical level of cholinesterase depletion is reached, grave symptoms appear. Whether death is actually caused entirely by cholinesterase depletion or by the disturbance of a number of enzymes is not yet known. Recovery is apparently complete if a poisoned animal or human has time to re-form a critical amount of cholinesterase. The organism exposed remains susceptible to relatively low dosages of parathion until the cholinesterase has regenerated. Small doses at frequent intervals are, therefore, more or less additive. There is no indication that, when recovery from a given exposure is entirely complete, the exposed organism is prejudiced in any way. Combustible when exposed to heat or flame. Violent reaction with endrin. Highly dangerous; shock can shatter the container, releasing the contents. A broad spectrum insecticide in agricultural applications. When heated to decomposition it emits highly toxic fumes of NOx, POx, and SOx.    

Parathion Standards and Recommendations

OSHA PEL: TWA 0.1 mg/m3 (skin)
ACGIH TLV: TWA 0.05 mg/m3 (skin); Not Classifiable as a Human Carcinogen)); BEI: 0.5 mg/g creatinine in urine at end of shift; Not Classifiable as a Human Carcinogen
DFG MAK: 0.1 mg/m3; BAT: 500 μg/L p-nitrophenol in urine after several shifts
NIOSH REL: (Parathion) TWA 0.05 mg/m3
DOT Classification:  6.1; Label: Poison

Parathion Analytical Methods

For occupational chemical analysis use OSHA: #ID-62 or NIOSH: EPN, Malathion, and Parathion, 5012.

Parathion Specification

 Parathion (CAS NO.56-38-2) is also named as 4-06-00-01337 (Beilstein Handbook Reference) ; AAT ; AATP ; AC 3422 ; AI3-15108 ; Alkron ; Alleron ; American cyanamid 3422 ; Aphamite ; Aralo ; BAY E-605 ; BRN 2059093 ; Bayer E-605 ; Bladan F ; CCRIS 493 ; Danthion ; Diethyl 4-nitrophenyl phosphorothionate ; Drexel parathion 8E ; E 605 ; E 605 F ; E 605 forte ; Ecatox 20 ; Ekatin WF & WF ULV ; Ekatox ; Ekatox 20 ; Ethyl parathion ; Ethyl parathion 50 EC ; Ethylparathion ; Fostox ; Nourithion ; O,O-Diaethyl-O-(4-nitro-phenyl)-monothiophosphat ; O,O-Diaethyl-O-(4-nitro-phenyl)-monothiophosphat [German] ; O,O-Diethyl O-(p-nitrophenyl) phosphorothioate ; O,O-Dietil-O-(4-nitro-fenil)-monotiofosfato ; Pacol ; Paradust ; Paramar ; Paramar 50 ; Paraphos ; Parathene ; Phenol, p-nitro-, O-ester with O,O-diethyl phosphorothioate ; Phenol, p-nitro-, O-ester with O,O-diethylphosphorothioate ; Phoskil ; Phosphemol ; Phosphenol ; RB ; RCRA waste number P089 ; Rhodiasol ; Thiomex ; Thiophos ; Thiophos 3422 ; Thiophosphate de O,O-diethyle et de O-(4-nitrophenyle) ; Thiophosphate de O,O-diethyle et de O-(4-nitrophenyle) [French] ; Tiofos ; UN 2783 ; Vapophos ; Vitrex ; p-Nitrophenyl diethyl thiophosphate . Parathion (CAS NO.56-38-2) is light-yellow liquid. It is slightly soluble in water. When heated to decomposition Parathion emits very toxic fumes of oxides of sulfur, phosphorus and nitrogen. It is highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. Parathion may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.