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Tolclofos-methyl

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Name

Tolclofos-methyl

EINECS 260-515-3
CAS No. 57018-04-9 Density 1.401 g/cm3
PSA 69.59000 LogP 4.84850
Solubility 1.10 mg l-1 (25 °C) Melting Point 78-80 °C
Formula C9H11Cl2O3PS Boiling Point 338.5 °C at 760 mmHg
Molecular Weight 301.13 Flash Point 158.5 °C
Transport Information N/A Appearance N/A
Safety 22-24/25-61-60-37-24 Risk Codes 43-50/53
Molecular Structure Molecular Structure of 57018-04-9 (Tolclofos-methyl) Hazard Symbols Xi,N
Synonyms

O,O-DimethylO-(2,6-dichloro-4-methylphenyl) phosphorothioate;Rhizolex;Rhizolex T 50;Rizolex;Tolclophos-methyl;O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl phosphorothioate;Tolclofos-methyl;Thiophosphate de O-(2,6-dichloro-4-méthylphényle) et de O,O-diméthyle;phosphorothioic acid, O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl ester;

Article Data 5

Tolclofos-methyl Synthetic route

2432-12-4

2,6-dichloro-4-methylophenol

2524-03-0

dimethyl chlorothiophosphate

7757-82-6

sodium sulfate

57018-04-9

tolclofos-methyl

Conditions
ConditionsYield
With potassium carbonate In water; toluene
2432-12-4

2,6-dichloro-4-methylophenol

2524-03-0

dimethyl chlorothiophosphate

57018-04-9

tolclofos-methyl

Conditions
ConditionsYield
With copper(l) chloride; sodium hydroxide In water; toluene at 45 - 50℃; for 4.5h;
57018-04-9

tolclofos-methyl

Mono-demethyl tolclofos-methyl

Conditions
ConditionsYield
With potassium dimethyldithiocarbamate In ethanol Ambient temperature;100%
57018-04-9

tolclofos-methyl

357-57-3

brucine

A

C23H26N2O4*C8H9Cl2O3PS

B

C23H26N2O4*C8H9Cl2O3PS

Conditions
ConditionsYield
In acetonitrile for 2h; Heating; Yield given. Yields of byproduct given;
57018-04-9

tolclofos-methyl

96790-20-4

2,6-dichloro-4-methylphenyl methyl phosphorochloridothionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / potassium dimethyldithiocarbamate / ethanol / Ambient temperature
2: 33 percent / PCl5 / CH2Cl2 / Ambient temperature
View Scheme

Tolclofos-methyl Specification

The O-2,6-Dichloro-p-tolyl O,O-dimethyl phosphorothioate, with the CAS registry number 57018-04-9 and EINECS registry number 260-515-3, has the systematic name of O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl phosphorothioate. It belongs to the product category of Fungicide, and the molecular formula of this chemical is C9H11Cl2O3PS. What's more, while dealing with this chemical, you should not breathe dust and then try to avoid contacting with skin and eyes. In addition, it should be sealed and stored at 2-8°C.

The physical properties of O-2,6-Dichloro-p-tolyl O,O-dimethyl phosphorothioate are as following: (1)ACD/LogP: 4.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.03; (4)ACD/LogD (pH 7.4): 4.03; (5)ACD/BCF (pH 5.5): 683.31; (6)ACD/BCF (pH 7.4): 683.31; (7)ACD/KOC (pH 5.5): 3720.67; (8)ACD/KOC (pH 7.4): 3720.67; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 69.59 Å2; (13)Index of Refraction: 1.563; (14)Molar Refractivity: 69.8 cm3; (15)Molar Volume: 214.8 cm3; (16)Polarizability: 27.67×10-24cm3; (17)Surface Tension: 48.1 dyne/cm; (18)Density: 1.401 g/cm3; (19)Flash Point: 158.5 °C; (20)Enthalpy of Vaporization: 55.89 kJ/mol; (21)Boiling Point: 338.5 °C at 760 mmHg; (22)Vapour Pressure: 0.000191 mmHg at 25°C.

Preparation and uses of O-2,6-Dichloro-p-tolyl O,O-dimethyl phosphorothioate: It can be prepared by 0.105mol 2,6-dichloro-4-methyl phenol and O, O-dimethyl thiophosphoryl chloride. The reaction will need solvent toluene, and acid-binding agent potassium carbonate. The reaction time id 2 hours with the temperature of 60-70°C, and the yield is 29.8g. What's more, it is usually used as organophosphorus germicides.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(cc(Cl)c1OP(=S)(OC)OC)C
(2)InChI: InChI=1/C9H11Cl2O3PS/c1-6-4-7(10)9(8(11)5-6)14-15(16,12-2)13-3/h4-5H,1-3H3
(3)InChIKey: OBZIQQJJIKNWNO-UHFFFAOYAH

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 826, 1991.
mouse LD50 intraperitoneal 1070mg/kg (1070mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A508, Pg. 1985,
mouse LD50 oral 3500mg/kg (3500mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A508, Pg. 1985,
mouse LD50 skin > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (41), Pg. 21, 1982.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (41), Pg. 21, 1982.
quail LD50 oral > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 8, Pg. 810, 1987.
rat LD50 intraperitoneal 4900mg/kg (4900mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A508, Pg. 1985,
rat LD50 oral 5gm/kg (5000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C265, 1991.
rat LD50 skin > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (41), Pg. 21, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (41), Pg. 21, 1982.

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