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Pendimethalin

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Name

Pendimethalin

EINECS 254-938-2
CAS No. 40487-42-1 Density 1.215 g/cm3
PSA 103.67000 LogP 4.83970
Solubility <0.5 mg/L in water Melting Point 56-57 °C
Formula C13H19N3O4 Boiling Point 421 °C at 760 mmHg
Molecular Weight 281.312 Flash Point 208.4 °C
Transport Information UN3077 9/PG 3 Appearance orange-yellow crystals
Safety 2-24-29-37-60-61-45-16-7 Risk Codes 43-50/53-39/23/24/25-23/24/25-11
Molecular Structure Molecular Structure of 40487-42-1 (Pendimethalin) Hazard Symbols IrritantXi, DangerousN, ToxicT, FlammableF
Synonyms

3,4-Dimethyl-2,6-dinitro-N-(1-ethylpropyl)aniline;3,4-Xylidine, 2,6-dinitro-N-(1-ethylpropyl)-;Benzenamine, 3,4-dimethyl-2,6-dinitro-N-(1-ethylpropyl)-;N-(1-Aethylpropyl)-2,6-dinitro-3,4-xylidin;Phenoxalin;

Article Data 23

Pendimethalin Synthetic route

N-(1-ethylpropyl)-2,6-dinitro-N-(3,4-dimethylphenyl)acetamide

Conditions
ConditionsYield
With sulfuric acid In water; 1,2-dichloro-ethane at 85℃; for 4h;99.1%
160754-06-3

3,4-dimethyl-2,6-dinitroanisole

616-24-0

3-aminopentane

Conditions
ConditionsYield
With calcium chloride at 50℃;93%

1,2,6-trinitro-o-xylene

616-24-0

3-aminopentane

A

3,4-dimethyl-2,6-dinitro-N-(ethylpropyl) aniline

Conditions
ConditionsYield
In methanolA 91%
B n/a
56038-89-2

N-(1-ethylpropyl)-3,4-dimethyl-benzenamine

108-90-7

chlorobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water; 1,2-dichloro-ethane
95-64-7

4-amino-o-xylene

A

73215-09-5

N-(1-ethylpropyl)-N,2,6-trinitro-3,4-xylidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
View Scheme
95-64-7

4-amino-o-xylene

B

1417827-06-5

C13H17N3O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
3.1: 0.17 h / 180 °C
View Scheme
Multi-step reaction with 3 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
3: 0.17 h / 180 °C
View Scheme
95-64-7

4-amino-o-xylene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
3.1: iron(III) chloride; hydrogenchloride / 3 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
3: iron(III) chloride; hydrogenchloride / 3 h / 75 °C
View Scheme
96-22-0

pentan-3-one

A

73215-09-5

N-(1-ethylpropyl)-N,2,6-trinitro-3,4-xylidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
View Scheme
96-22-0

pentan-3-one

B

1417827-06-5

C13H17N3O4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
3.1: 0.17 h / 180 °C
View Scheme
Multi-step reaction with 3 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
3: 0.17 h / 180 °C
View Scheme
96-22-0

pentan-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1.1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2.1: nitric acid / 30 °C
2.2: 30 - 60 °C
3.1: iron(III) chloride; hydrogenchloride / 3 h / 75 °C
View Scheme
Multi-step reaction with 3 steps
1: platinum on carbon; naphthalene-2-sulfonate; hydrogen / 1 h / 60 - 70 °C / 3750.38 - 7500.75 Torr / Autoclave; Inert atmosphere
2: nitric acid / 1,2-dichloro-ethane; water / 1 h / 60 °C
3: iron(III) chloride; hydrogenchloride / 3 h / 75 °C
View Scheme

Pendimethalin Specification

The IUPAC name of 3,4-Dimethyl-2,6-dinitro-N-(1-ethylpropyl)-benzenamine is 3,4-dimethyl-2,6-dinitro-N-pentan-3-ylaniline. With the CAS registry number 40487-42-1, it is also named as 3,4-Xylidine, 2,6-dinitro-N-(1-ethylpropyl)-. The product's categories are Herbicide; Dinitroaniline Pesticides & Metabolites; N-PAlphabetic; P; PA - PEN. It is orange-yellow crystals which is toxic. When heated to decomposition it emits toxic fumes of NOx. So the storage environment should be well- ventilated, low-temperature and dry. Keep this chemical separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.56; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.56; (4)ACD/LogD (pH 7.4): 5.56; (5)ACD/BCF (pH 5.5): 9973.73; (6)ACD/BCF (pH 7.4): 9973.73; (7)ACD/KOC (pH 5.5): 25349.63; (8)ACD/KOC (pH 7.4): 25349.63; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.58; (13)Molar Refractivity: 77.09 cm3; (14)Molar Volume: 231.5 cm3; (15)Surface Tension: 47.8 dyne/cm; (16)Enthalpy of Vaporization: 67.5 kJ/mol; (17)Vapour Pressure: 2.69E-07 mmHg at 25°C; (18)Rotatable Bond Count: 4; (19)Exact Mass: 281.137556; (20)MonoIsotopic Mass: 281.137556; (21)Topological Polar Surface Area: 104; (22)Heavy Atom Count: 20; (23)Complexity: 349.

Preparation of 3,4-Dimethyl-2,6-dinitro-N-(1-ethylpropyl)-benzenamine: It can be obtained by alkylation and nitration of 3,4-aminodimethylbenzene.

Uses of 3,4-Dimethyl-2,6-dinitro-N-(1-ethylpropyl)-benzenamine: It is a herbicides used in premergence and postemergence application to control annual grasses and certain broadleaf weeds. So it protects crops like wheat, corn, soybeans potatoes, cabbage, peas, carrots and asparagus. It also can be used to produce N2-(1-ethyl-propyl)-4,5-dimethyl-3-nitro-benzene-1,2-diamine and 3-(1-ethyl-propylamino)-6-methyl-2-nitro-4-nitroso-benzaldehyde. This reaction needs reagent sodium-sulphide nonahydrate, sodium bicarbonate and solvent H2O, methanol at ambient temperature. The reaction time is 16 hours. The yield is 56%.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition. It is not only toxic by inhalation, in contact with skin and if swallowed, but also very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. What's more, it has danger of very serious irreversible effects. So people should avoid contact with skin and not empty into drains. If you want to contact this product, you must wear suitable gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) This material and its container must be disposed of as hazardous waste. Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure. 
1. SMILES:[O-][N+](=O)c1c(c(cc([N+]([O-])=O)c1NC(CC)CC)C)C
2. InChI:InChI=1/C13H19N3O4/c1-5-10(6-2)14-12-11(15(17)18)7-8(3)9(4)13(12)16(19)20/h7,10,14H,5-6H2,1-4H3
3. InChIKey:CHIFOSRWCNZCFN-UHFFFAOYAS

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 656, 1991.
mouse LD50 intraperitoneal 220mg/kg (220mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Indian Journal of Experimental Biology. Vol. 25, Pg. 463, 1987.
 
mouse LD50 oral 1340mg/kg (1340mg/kg)   Pesticide Manual. Vol. 9, Pg. 656, 1991.
rabbit LD50 skin 2260mg/kg (2260mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C254, 1991.
rat LD50 intraperitoneal 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Indian Journal of Experimental Biology. Vol. 25, Pg. 463, 1987.
rat LD50 oral 1050mg/kg (1050mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A314, Pg. 1984,

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