2-methoxy-3,6-dichlorobenzaldehyde
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With sodium hypochlorite In toluene at 25℃; for 5h; Temperature; Solvent; Reagent/catalyst; Time; | 95.5% |
Conditions | Yield |
---|---|
In methanol at 40 - 65℃; for 2h; Temperature; | 95.5% |
In methanol at 40 - 68℃; for 2h; | 208.7 g |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 95% |
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 |
3',6'-dichloro-2'-methoxyacetophenone
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With sodium hypochlorite In toluene at 5 - 20℃; for 8h; | 88.6% |
With sodium carbonate In water for 8h; Reagent/catalyst; Reflux; | 68% |
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With potassium permanganate In tert-butyl alcohol at 80℃; | 83% |
Conditions | Yield |
---|---|
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% |
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With sodium carbonate In water for 8h; Reagent/catalyst; Reflux; | 81.6% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium hydroxide; dimethyl sulfate In water |
1-Adamantanethiol
methyl 2,5-dichloro-6-methoxybenzoate
A
methyl 3,6-bis(1-adamantylthio)-2-methoxybenzoate
B
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
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 |
1-Adamantanethiol
methyl 2,5-dichloro-6-methoxybenzoate
thiophenol
A
C20H16O2S2
B
methyl 2-methoxy-3,6-bis(phenylthio)benzoate
C
methyl 3,6-bis(1-adamantylthio)-2-methoxybenzoate
D
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
Stage #1: 1-Adamantanethiol; thiophenol With potassium tert-butylate In ammonia liquid NH3; Stage #2: methyl 3,6-dichloro-2-methoxybenzoate With ammonia for 2h; UV-irradiation; | A 38 %Chromat. B 48 %Chromat. C 9 %Chromat. D n/a |
methyl 2,5-dichloro-6-methoxybenzoate
thiophenol
A
methyl 2-methoxy-3,6-bis(phenylthio)benzoate
B
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
Stage #1: thiophenol With potassium tert-butylate In ammonia liquid NH3; Stage #2: methyl 3,6-dichloro-2-methoxybenzoate With ammonia for 2h; UV-irradiation; | A 80 %Chromat. B n/a |
dicamba 2-nitrobenzyl ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 182h; Time; Solvent; Reagent/catalyst; Sealed tube; UV-irradiation; |
dicamba 4-methoxyphenacylmethyl ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 35℃; for 28h; Time; Sealed tube; UV-irradiation; |
dicamba 4-butoxyphenacylmethyl ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 35℃; for 168h; Time; Solvent; Reagent/catalyst; Sealed tube; UV-irradiation; |
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
In tetrahydrofuran at 35℃; for 210h; Time; Solvent; Reagent/catalyst; Sealed tube; UV-irradiation; |
dicamba 2-hydroxypyridine ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 392h; Time; Sealed tube; Darkness; |
dicamba maleic hydrazide diester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 196h; Time; Sealed tube; Darkness; |
3,6-dichloro-2-methoxybenzoic acid chloride
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h 2: water / acetonitrile / 392 h / 35 °C / Darkness View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 11 h 2: water; acetonitrile / 392 h / 35 °C / UV-irradiation View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 15 h / 20 °C 2: water / acetonitrile / 182 h / 35 °C / Sealed tube; UV-irradiation View Scheme |
dicamba 4-methoxybenzyl ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 196h; Time; Sealed tube; Darkness; |
dicamba 4-methoxyphenol ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
In water; acetonitrile at 35℃; for 392h; Time; UV-irradiation; |
ethyl 2-(2-nitrobenzyl dicambyl)acrylate
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 294h; Time; Sealed tube; UV-irradiation; |
2-(3-oxobutyl)-6-dicambyl-2,3-dihydro-3-pyridazinone
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 392h; Time; Darkness; |
2-(3-oxopropyl)-6-dicambyl-2,3-dihydro-3-pyridazinone
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 392h; Time; Sealed tube; UV-irradiation; |
2-(2-cyanoethyl)-6-dicambyl-3(2H)-pyridazinone
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 392h; Time; Sealed tube; Darkness; |
3-cyano-4,6-di-t-butyl-2-pyridone dicamba ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 294h; Time; Sealed tube; Darkness; |
dicamba 2-nitrobenzyl ester
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
In water; acetonitrile at 35℃; for 392h; Time; Solvent; Reagent/catalyst; UV-irradiation; |
2-(3-carboxyethyl-propyl)-6-dicambyl-3(2H)-pyridazinone
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
With water In acetonitrile at 35℃; for 98h; Time; Sealed tube; Darkness; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: potassium hydroxide / methanol; water / 20 h / 200 °C 2: sulfuryl dichloride; diisobutylamine / toluene / 2 h / 70 °C 3: potassium carbonate / acetone / 3 h / 56 °C 4: potassium permanganate / tert-butyl alcohol / 80 °C View Scheme |
3,6-dichloro-O-anisic acid
1,1-dimethylpiperidinium hydroxide
1,1-dimethylpiperidinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
In water at 20℃; Green chemistry; | 99% |
3,6-dichloro-O-anisic acid
4-butyl-4-methylmorpholinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
In water at 20℃; Green chemistry; | 99% |
3,6-dichloro-O-anisic acid
1-butyl-1-methylpyrrolidinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
In water at 20℃; Green chemistry; | 99% |
3,6-dichloro-O-anisic acid
didecyldimethylammonium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: bis(decyl)dimethylazanium halide In water at 20℃; for 0.5h; Green chemistry; | 99% |
3,6-dichloro-O-anisic acid
dodecyldimethylphenoxyethylammonium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: dodecyldimethyl(2-phenoxyethyl)azanium halide In water at 20℃; for 0.5h; Green chemistry; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water Heating; Stage #2: C23H39ClNO3(1+)*Br(1-) In water; isopropyl alcohol | 99% |
Conditions | Yield |
---|---|
at 60℃; under 3.75038 Torr; for 10h; | 99% |
Conditions | Yield |
---|---|
at 60℃; under 3.75038 Torr; for 10h; | 99% |
Conditions | Yield |
---|---|
Stage #1: cetyltrimethylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: 3,6-dichloro-O-anisic acid In methanol at 25℃; | 98% |
Conditions | Yield |
---|---|
Stage #1: trimethyloctadecylammonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: 3,6-dichloro-O-anisic acid In methanol at 25℃; | 98% |
Conditions | Yield |
---|---|
Stage #1: behentrimonium chloride With potassium hydroxide In methanol for 0.166667h; Stage #2: 3,6-dichloro-O-anisic acid In methanol at 25℃; | 98% |
Conditions | Yield |
---|---|
In methanol at 25℃; under 759.826 Torr; | 98% |
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
at 25℃; | 96% |
Conditions | Yield |
---|---|
With sodium hydroxide In water | 96% |
diallyldimethylammonium hydroxide
3,6-dichloro-O-anisic acid
diallyldimethylammonium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
In water at 20℃; Green chemistry; | 95% |
3,6-dichloro-O-anisic acid
cyclododecyloxymethyl(2-hydroxyethyl)dimethylammonium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: cyclododecyloxymethyl(2-hydroxyethyl)dimethylammonium halide In water at 20℃; for 0.5h; Green chemistry; | 95% |
3,6-dichloro-O-anisic acid
acidine
4-Chloro-2-methylphenoxyacetic acid potassium salt
Conditions | Yield |
---|---|
In methanol at 60℃; for 2h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water Heating; Stage #2: C22H37ClNO3(1+)*Br(1-) In water; isopropyl alcohol | 95% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; Inert atmosphere; | 94% |
3,6-dichloro-O-anisic acid
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water Heating; Stage #2: C24H48NO(1+)*Br(1-) In water; isopropyl alcohol | 93.9% |
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0 - 80℃; | 92% |
3,6-dichloro-O-anisic acid
(2-hydroxyethyl)dimethyl(undecyloxymethyl)ammonium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: (2-hydroxyethyl)dimethyl(undecyloxymethyl)ammonium halide In water at 20℃; for 0.5h; Green chemistry; | 92% |
3,6-dichloro-O-anisic acid
1-decyl-1-methylpiperidinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: 1-decyl-1-methylpiperidinium halide In water at 20℃; for 0.5h; Green chemistry; | 92% |
Conditions | Yield |
---|---|
In methanol at 25℃; under 759.826 Torr; | 92% |
3,6-dichloro-O-anisic acid
N-dodecylpyridinium chloride
1-dodecylpyridinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
With potassium hydroxide In water at 20 - 60℃; for 24h; | 91% |
3,6-dichloro-O-anisic acid
1-dodecylpyridinium 3,6-dichloro-2-methoxybenzoate
Conditions | Yield |
---|---|
Stage #1: 3,6-dichloro-O-anisic acid With sodium hydroxide In water at 50℃; Green chemistry; Stage #2: 1-dodecylpyridinium halide In water at 20℃; for 0.5h; Green chemistry; | 91% |
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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