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Metazachlor

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Name

Metazachlor

EINECS 266-583-0
CAS No. 67129-08-2 Density 1.19 g/cm3
PSA 38.13000 LogP 2.72940
Solubility N/A Melting Point 74-78 °C
Formula C14H16ClN3O Boiling Point 439.2 °C at 760 mmHg
Molecular Weight 277.754 Flash Point 219.4 °C
Transport Information N/A Appearance N/A
Safety 36-26-16 Risk Codes 22-36-20/21/22-11
Molecular Structure Molecular Structure of 67129-08-2 (Metazachlor) Hazard Symbols HarmfulXn, FlammableF
Synonyms

BAS 479;BAS 47902H;BAS 479H;Butisan 400SC;Butisan S;Methazachlor;Pree;

Article Data 14

Metazachlor Synthetic route

125709-82-2

1-(N-2,6-dimethylaniline)-1-(1N-pyrazol)-methane

79-04-9

chloroacetyl chloride

67129-08-2

Metazachlor

Conditions
ConditionsYield
In cyclohexane for 6h; Reflux; Green chemistry; Industrial scale;95%
288-13-1

NH-pyrazole

61706-54-5

N-(chloromethyl)-N-(2,6-dimethylphenyl)-α-chloroacetamide

67129-08-2

Metazachlor

Conditions
ConditionsYield
In toluene at 74℃; under 217.522 Torr; for 12h; Temperature; Time; Pressure; Concentration;
67129-08-2

Metazachlor

N-((1H-pyrazol-1-yl)methyl)-N-(2,6-dimethylphenyl)acetamide

Conditions
ConditionsYield
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 44h; Autoclave;93%
With hydrogen; triethylamine In ethanol; water at 120℃; under 22502.3 - 37503.8 Torr; for 44h; Autoclave;93%
67129-08-2

Metazachlor

125709-81-1

2-hydroxy-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetamide

Conditions
ConditionsYield
potassium hydroxide In water for 4h; Product distribution; Mechanism; Heating; variation of catalyst concentration, reaction time;75%
potassium hydroxide In water for 4h; Heating;75%
67129-08-2

Metazachlor

A

288-13-1

NH-pyrazole

B

4073-98-7

4,4'-methylenebis(2,6-dimethylaniline)

Conditions
ConditionsYield
hydrogenchloride In water for 8h; Heating;A 59%
B 35%
67129-08-2

Metazachlor

A

288-13-1

NH-pyrazole

B

4073-98-7

4,4'-methylenebis(2,6-dimethylaniline)

C

1131-01-7

2-chloro-N-(2,6-dimethylphenyl)acetamide

Conditions
ConditionsYield
hydrogenchloride In water for 5h; Product distribution; Mechanism; Heating; variation of catalyst concentration, reaction time;A 47%
B 21%
C 12%
67129-08-2

Metazachlor

A

288-13-1

NH-pyrazole

B

1131-01-7

2-chloro-N-(2,6-dimethylphenyl)acetamide

Conditions
ConditionsYield
hydrogenchloride In water for 2h; Heating;A 40%
B 42%
67129-08-2

Metazachlor

125709-83-3

4,4'-methylenebis-(N-acetyl-2,6-dimethylbenzenamine)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 35 percent / 2.56 N hydrochloric acid / H2O / 8 h / Heating
2: 85 percent / benzene / 2 h / Heating
View Scheme
141-82-2

malonic acid

67129-08-2

Metazachlor

metazachlor malonic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;
144-62-7

oxalic acid

67129-08-2

Metazachlor

metazachlor oxalic acid

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;

Metazachlor Consensus Reports

Metazachlor  is reported in EPA TSCA Inventory.

Metazachlor Specification

The Metazachlor, with the CAS registry number 67129-08-2, is also known as 2-Chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)acetamide. It belongs to the product categories of Meta-meth Pesticides&Metabolites; Alpha sort; AmidePesticides&Metabolites; Herbicides; H-MAlphabetic; M; Pesticides&Metabolites; Pyrazole. Its EINECS registry number is 266-583-0. Its IUPAC name is called 2-chloro-N-(2,6-dimethylphenyl)-N-(pyrazol-1-ylmethyl)acetamide. You must keep it under seal in cool and dry place and far away from oxidizing agent. This chemical's classification codes are Agricultural Chemical; Herbicide.

Physical properties of Metazachlor: (1)ACD/LogP: 2.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.11; (4)ACD/LogD (pH 7.4): 2.11; (5)ACD/BCF (pH 5.5): 23.48; (6)ACD/BCF (pH 7.4): 23.49; (7)ACD/KOC (pH 5.5): 333.19; (8)ACD/KOC (pH 7.4): 333.3; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 78.01 cm3; (14)Molar Volume: 232.1 cm3; (15)Surface Tension: 42.5 dyne/cm; (16)Density: 1.19 g/cm3; (17)Melting Point: 74-78 °C; (18)Flash Point: 219.4 °C; (19)Enthalpy of Vaporization: 69.61 kJ/mol; (20)Boiling Point: 439.2 °C at 760 mmHg; (21)Vapour Pressure: 6.5E-08 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,6-dimethylaniline and formaldehyde. Then the intermediate product reacts with chloro-acetyl chloride. In the end, it will conduct a condensation reaction with Pyrazole.

Uses of Metazachlor: it can be used to produce bis-(4-amino-3,5-dimethyl-phenyl)-methane. This reaction will need catalytic agent 2.56 N hydrochloric acid and solvent H2O with reaction time of 8 hours. The yield is about 35%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health and may catch fire in contact with air which only need brief contact with an ignition source and has a very low flash point or evolve highly flammable gases in contact with water. In addition, it is highly flammable and is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes. You should keep it away from sources of ignition - No smoking. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1=C(C(=CC=C1)C)N(CN2C=CC=N2)C(=O)CCl
(2)InChI: InChI=1S/C14H16ClN3O/c1-11-5-3-6-12(2)14(11)18(13(19)9-15)10-17-8-4-7-16-17/h3-8H,9-10H2,1-2H3
(3)InChIKey: STEPQTYSZVCJPV-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 1gm/kg (1000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C54, 1991.
rat LD50 skin > 6810mg/kg (6810mg/kg)   Pesticide Manual. Vol. 9, Pg. 560, 1991.

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