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3689-24-5

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Basic Information
CAS No.: 3689-24-5
Name: SULFOTEP
Article Data: 29
Molecular Structure:
Molecular Structure of 3689-24-5 (SULFOTEP)
Formula: C8H20 O5 P2 S2
Molecular Weight: 322.323
Synonyms: Thiodiphosphoricacid ([(HO)2P(S)]2O), tetraethyl ester (9CI);Thiopyrophosphoric acid ([(HO)2PS]2O),tetraethyl ester (8CI);ASP 47;Bladafum;Dithiofos;Dithion;Dithione;Dithiophos;Dithiotep;E 393;Ethyl thiopyrophosphate ([(EtO)2PS]2O);Fulex;NSC 66403;O,O,O,O-Tetraethyl dithiopyrophosphate;Plantfume 103;Sulfotep;Sulfotepp;TEDP;TEDTP;Thiotepp;
EINECS: 222-995-2
Density: 1.256g/cm3
Melting Point: 60-67°C
Boiling Point: 318.7°Cat760mmHg
Flash Point: 146.5°C
Solubility: 30 mg/L at 20 °C (Worthing and Hance, 1991)
Hazard Symbols: Toxic by ingestion, inhalation, and skin absorption; cholinesterase inhibitor; use may be restricted. TLV: 0.2 mg/m3; not classifiable as a human carcinogen. Toxic by skin absorption.
Risk Codes: 27/28-50/53-67-65-38-11
Safety: Poison by ingestion, skin contact, inhalation, intramuscular, intraperitoneal, subcutaneous, and intravenous routes. A cholinesterase inhibitor type of insecticide. When heated to decomposition it emits toxic fumes of POx and SOx. See also PARATHION.
PSA: 129.95000
LogP: 4.89920
Synthetic route
31403-66-4, 83842-53-9

3-chloro-2-methyl-quinolin-4-ol

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93516-24-6

Thiophosphoric acid O-(3-chloro-2-methyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 74%
65673-93-0

3-Chlor-4-hydroxy-7-trifluormethylchinolin

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93516-26-8

Thiophosphoric acid O-(3-chloro-7-trifluoromethyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 72%
607-67-0

4-hydroxy-2-methylquinoline

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

22439-40-3

Quinothion

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 70%
86-99-7

7-chloro-4-hydroxylquinoline

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93516-22-4

Thiophosphoric acid O-(7-chloro-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 69%
529-37-3

4(1H)-quinolinone

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93516-19-9

Thiophosphoric acid O,O'-diethyl ester O''-quinolin-4-yl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 66%
322-97-4

7-trifluoromethyl-quinolin-4-ol

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93516-25-7

Thiophosphoric acid O,O'-diethyl ester O''-(7-trifluoromethyl-quinolin-4-yl) ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 55h;A n/a
B 65%
10352-60-0

2,3-dimethylquinolin-4-ol

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

93644-61-2

Thiophosphoric acid O-(2,3-dimethyl-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 63%
2524-04-1

diethyl phosphorochloridothioate

58861-80-6

4,5-dihydro-5-methyl-1,2,4-triazine-6(1H)-one

A

3689-24-5

sulfotep

B

135492-37-4

(5-Methyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile a) 1 h, 35 deg C, b) 4 h, 50 deg C;A n/a
B 63%
2524-04-1

diethyl phosphorochloridothioate

152210-26-9, 93516-30-4

3,7-dichloroquinolin-4-ol

A

3689-24-5

sulfotep

B

93516-27-9

3,7-Dichloro-1-ethyl-1H-quinolin-4-one

C

93516-23-5

Thiophosphoric acid O-(3,7-dichloro-quinolin-4-yl) ester O',O''-diethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide In tetrachloromethane at 60℃; for 72h;A n/a
B 16%
C 62%
128070-22-4

5-benzyl-4,5-dihydro-1,2,4-triazin-6(1H)-one

2524-04-1

diethyl phosphorochloridothioate

A

3689-24-5

sulfotep

B

135492-46-5

(5-Benzyl-6-oxo-5,6-dihydro-1H-[1,2,4]triazin-4-yl)-phosphonothioic acid O,O-diethyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;A n/a
B 53%
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Chemistry

IUPAC Name:Diethoxyphosphinothioyloxy-diethoxy-sulfanylidene-λ5-phosphane
Synonyms: O,O,O',O'-Tetraethyldithiopyro phosphate;thiotep ; Thiotepp(r) ; Thiodiphosphoric acid tetraethyl ester ; Tetraethyldithio pyrophosphate ; Sulfotep ; Sulfotepp ; Bis-o,o-diethylphosphorothionic anhydrid
Product categories: insecticide
CAS: 3689-24-5
Molecular Formula: C8H20O5P2S2
Molecular Weight: 322.32
Molecular Struture:
EINECS: 222-995-2
Mol File: 3689-24-5.mol
Surface Tension: 48.2 dyne/cm
Density: 1.256 g/cm3
Flash Point: 146.5 °C
Enthalpy of Vaporization: 53.79 kJ/mol
Boiling Point: 318.7 °C at 760 mmHg
Vapour Pressure: 0.000663 mmHg at 25°C
Index of Refraction: 1.505
Storage temp: APPROX 4°C
Merck : 13,9056

Uses

Sulfotep (3689-24-5) is non-absorption of pesticide,which is mainly used for prevention and control of rice and cotton pests.

Production

 Sulfotep (3689-24-5) can be obtained from O, O-Diethyl phosphorus chloride pyridine hydrolysis and condensation in the presence of deacidification.

Toxicity Data With Reference

1.    

orl-rat LD50:5 mg/kg

    ARSIM*    Agricultural Research Service, USDA Information Memorandum. 20 (1966),24.
2.    

ihl-rat LC50:38 mg/m3/4H

    ARTODN    Archives of Toxicology. 33 (1974),1.
3.    

skn-rat LD50:65 mg/kg

    ARTODN    Archives of Toxicology. 33 (1974),1.
4.    

ipr-rat LD50:6600 µg/kg

    ARTODN    Archives of Toxicology. 33 (1974),1.
5.    

ims-rat LD50:55 µg/kg

    CJCHAG    Canadian Journal of Chemistry. 34 (1956),1819.
6.    

orl-mus LD50:22 mg/kg

    ARTODN    Archives of Toxicology. 33 (1974),1.
7.    

ihl-mus LC50:40 mg/m3/4H

    ARTODN    Archives of Toxicology. 33 (1974),1.
8.    

ipr-mus LD50:940 µg/kg

    CJCHAG    Canadian Journal of Chemistry. 34 (1956),1819.
9.    

scu-mus LD50:8 mg/kg

    PAREAQ    Pharmacological Reviews. 11 (1959),636.
10.    

ivn-mus LD50:300 µg/kg

    CJCHAG    Canadian Journal of Chemistry. 34 (1956),1819.
11.    

ims-mus LD50:500 µg/kg

Safety Profile

Hazard Codes  T+,N,Xn,F
Risk Statements  27/28-50/53-67-65-38-11
11:  Highly Flammable 
38:  Irritating to the skin 
65:  Harmful: May cause lung damage if swallowed 
67:  Vapors may cause drowsiness and dizziness 
27/28:  Very Toxic in contact with skin and if swallowed 
50/53:  Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment 
Safety Statements  23-28-36/37-45-60-61-62
23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
28:  After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
60:  This material and/or its container must be disposed of as hazardous waste 
61:  Avoid release to the environment. Refer to special instructions safety data sheet 
62:  If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label 
36/37:  Wear suitable protective clothing and gloves 
RIDADR  1704
RTECS  XN4375000
HazardClass  6.1(a)
PackingGroup  II

Standards and Recommendations

OSHA PEL: TWA 0.2 mg/m3 (skin)
ACGIH TLV: TWA 0.2 mg/m3 (skin); Not Classifiable as a Human Carcinogen
DFG MAK: 0.0075 ppm (0.1 mg/m3)
DOT Classification:  6.1; Label: Poison

Specification

General Description: Tetraethyl dithiopyrophosphate and compressed gas mixture is a liquid charged with a gas. Tetraethyl dithiopyrophosphate is a yellow liquid. Its vapor is heavier than air. Sulfotep (3689-24-5) is lethal by skin absorption and inhalation. Prolonged exposure of the containers to fire or heat may result in their violent rupturing and rocketing.
Reactivity Profile: Organothiophosphates, such as Tetraethyl dithiopyrophosphate, 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. Sulfotep is incompatible with the following: Strong oxidizers, iron.