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Dicamba

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Name

Dicamba

EINECS 217-635-6
CAS No. 1918-00-9 Density 1.474 g/cm3
PSA 46.53000 LogP 2.70020
Solubility 50 g/100 mL in water Melting Point 112-116 °C(lit.)
Formula C8H6Cl2O3 Boiling Point 326.1 °C at 760 mmHg
Molecular Weight 243.022 Flash Point 151 °C
Transport Information UN 3077 9/PG 3 Appearance white solid
Safety 26-61-36-16 Risk Codes 22-41-52/53-36-20/21/22-11
Molecular Structure Molecular Structure of 1918-00-9 (Dicamba) Hazard Symbols HarmfulXn,DangerousN,FlammableF
Synonyms

Banvel SGF;Banvel 480;MDBA;Banvel;Benzoic acid,3,6-dichloro-2-methoxy-;Mediben;3,6-Dichloro-2-methoxybenzoic acid;dicamba;2,5-dichloro-6-methoxybenzoic acid; 2-methoxy-3,6-dichlorobenzoic acid;

Article Data 48

Dicamba Synthetic route

27164-08-5

2-methoxy-3,6-dichlorobenzaldehyde

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With sodium hypochlorite In toluene at 25℃; for 5h; Temperature; Solvent; Reagent/catalyst; Time;95.5%

2-bromo-3,6-dichlorobenzoic acid

124-41-4

sodium methylate

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
In methanol at 40 - 65℃; for 2h; Temperature;95.5%
In methanol at 40 - 68℃; for 2h;208.7 g
6597-78-0

methyl 2,5-dichloro-6-methoxybenzoate

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With sodium hydroxide In water95%
With potassium tert-butylate; ammonia for 2h; UV-irradiation;
With water at 60℃; for 3h; Acidic conditions;14.5 g
With water; sodium hydroxide
With water Alkaline conditions; Large scale;1574 kg
73239-05-1

3',6'-dichloro-2'-methoxyacetophenone

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With sodium hypochlorite In toluene at 5 - 20℃; for 8h;88.6%
With sodium carbonate In water for 8h; Reagent/catalyst; Reflux;68%

1,4-dichloro-2-methoxy-3-methylbenzene

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With potassium permanganate In tert-butyl alcohol at 80℃;83%
50-31-7

2,3,6-TBA

124-41-4

sodium methylate

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
Stage #1: 2,3,6-TBA; sodium methylate In methanol at 85℃; under 15001.5 Torr; for 8h; Autoclave;
Stage #2: With sodium hydroxide at 100℃; for 2h; pH=11 - 12; Temperature;
82%
Stage #1: 2,3,6-TBA With sodium hydroxide In methanol at 50℃; for 2h;
Stage #2: sodium methylate In methanol; dimethyl sulfoxide at 70℃; for 9h;
78%

2-methoxy-3,6-dichloroprop-1-enylbenzene

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With sodium carbonate In water for 8h; Reagent/catalyst; Reflux;81.6%
74-87-3

methylene chloride

4-bromo-3,6-dichlorosalicylic acid

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
Stage #1: 5-bromo-3,6-dichlorosalicylic acid With 5%-palladium/activated carbon; hydrogen; sodium acetate In acetic acid at 20℃; under 760.051 Torr; for 2h;
Stage #2: methylene chloride With sodium hydroxide In water at 85℃; under 4654.46 Torr; for 10h;
75%
3401-80-7

3,6-dichloro-2-hydroxybenzoic acid

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
With potassium hydroxide; dimethyl sulfate In water
34301-54-7

1-Adamantanethiol

6597-78-0

methyl 2,5-dichloro-6-methoxybenzoate

A

1353055-84-1

methyl 3,6-bis(1-adamantylthio)-2-methoxybenzoate

B

1918-00-9

3,6-dichloro-O-anisic acid

Conditions
ConditionsYield
Stage #1: 1-Adamantanethiol With potassium tert-butylate In ammonia liquid NH3;
Stage #2: methyl 3,6-dichloro-2-methoxybenzoate With ammonia for 2h; UV-irradiation;
A 98 %Chromat.
B n/a

Dicamba Consensus Reports

EPA Genetic Toxicology Program.

Dicamba Specification

The 2-Methoxy-3,6-dichlorobenzoic acid is a halogenated benzoic acid derivative which is stable to oxidation and hydrolysis. The IUPAC name of this chemical is 3,6-dichloro-2-methoxybenzoic acid. With the CAS registry number 1918-00-9, it is also named as Dicamba. The product's categories are fine chemical & intermediates; organic acids. It is white solid dissolved in a liquid carrier. It is toxic and flammable by fire. In addition, it will produce toxic chloride gas when buring, so the storage environment should be ventilate, low-temperature and dry. And keep 2-Methoxy-3,6-dichlorobenzoic acid separate from raw materials of food. It acts by increasing plant growth rate. At sufficient concentrations, the plant outgrows its nutrient supplies, and dies.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): -0.39; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.13; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.576; (13)Molar Refractivity: 49.65 cm3; (14)Molar Volume: 149.8 cm3; (15)Polarizability: 19.68×10-24 cm3; (16)Surface Tension: 49.6 dyne/cm; (17)Enthalpy of Vaporization: 59.99 kJ/mol; (18)Vapour Pressure: 8.98E-05 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 219.969399; (21)MonoIsotopic Mass: 219.969399; (22)Topological Polar Surface Area: 46.5; (23)Heavy Atom Count: 13.

Preparation of 2-Methoxy-3,6-dichlorobenzoic acid: By the 1,2,4-trichlorobenzene reacts with CH3OH / NaOH to get 2,5-dichlorophenol which reacts with CO2 under pressure to obtain 2-hydroxy-3,6-dichloro benzoic acid. Then, we can get the product by the reaction of 2-hydroxy-3,6-dichloro benzoic acid and (CH3)2SO4.

Uses of 2-Methoxy-3,6-dichlorobenzoic acid: It is an herbicide used to control brush and bracken in pastures. And it is also used to control annual and perennial rose weeds in grain crops and highlands. It will kill legumes and broadleaf weeds before and after they sprout. In combination with a phenoxyalkanoic acid or another herbicide, dicamba is used in pastures, range land, and noncrop areas (fence rows, roadways and wastage) to control weeds.

When you are using this chemical, please be cautious about it as the following: 
It is harmful by inhalation, in contact with skin and if swallowed. It is also irritating to eyes and has serious damage to the eyes, so in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.. In addition, this chemical is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. If you want to contact this product, you must wear suitable protective clothing. Avoid release to the environment. 

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1ccc(Cl)c(c1OC)C(=O)O
2. InChI:InChI=1/C8H6Cl2O3/c1-13-7-5(10)3-2-4(9)6(7)8(11)12/h2-3H,1H3,(H,11,12)

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 3gm/kg (3000mg/kg)   Hygiene and Sanitation Vol. 35(7-9), Pg. 14, 1970.
mammal (species unspecified) LD50 unreported 1gm/kg (1000mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 147, 1971.
mouse LD50 oral 1190mg/kg (1190mg/kg)   Hygiene and Sanitation Vol. 35(7-9), Pg. 14, 1970.
mouse LD50 unreported 700mg/kg (700mg/kg)   Tsitologiya i Genetika. Cytology and Genetics. For English translation, see CYGEDX. Vol. 16(1), Pg. 45, 1982.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Hygiene and Sanitation Vol. 35(7-9), Pg. 14, 1970.
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Pesticide Manual. Vol. 9, Pg. 245, 1991.
rat LD50 oral 1039mg/kg (1039mg/kg)   Fundamental and Applied Toxicology. Vol. 7, Pg. 299, 1986.
rat LD50 skin > 1gm/kg (1000mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.

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