Dicamba

Base Information

• Chemical Name: Dicamba
• CAS No.: 1918-00-9
• Deprecated CAS: 62610-39-3,856565-78-1
• Molecular Formula: C8H6Cl2O3
• Molecular Weight: 243.022
• Hs Code.: 29189900
• European Community (EC) Number: 217-635-6
• ICSC Number: 0139
• UN Number: 3082,2769
• UNII: SJG3M6RY6H
• DSSTox Substance ID: DTXSID4024018
• Nikkaji Number: J3.382K
• Wikipedia: Dicamba
• Wikidata: Q424684
• Metabolomics Workbench ID: 143629
• ChEMBL ID: CHEMBL476936
• Mol file: 1918-00-9.mol

Synonyms:Dicamba

Chemical Property of Dicamba

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 8.98E-05mmHg at 25°C
• Melting Point: 112-116 °C(lit.)
• Refractive Index: 1.576
• Boiling Point: 326.1 °C at 760 mmHg
• PKA: 2.40±0.25(Predicted)
• Flash Point: 151 °C
• PSA: 46.53000
• Density: 1.474 g/cm³
• LogP: 2.70020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 50 g/100 mL
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 219.9693994
• Heavy Atom Count: 13
• Complexity: 198
• Transport DOT Label: Class 9

Purity/Quality:

99% ^*data from raw suppliers

Dicamba ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,F
• Hazard Codes: Xn,N,F
• Statements: 22-41-52/53-36-20/21/22-11
• Safety Statements: 26-61-36-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Herbicides, Chlorophenoxy
• Canonical SMILES: COC1=C(C=CC(=C1C(=O)O)Cl)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the skin and respiratory tract.
• Description: Dicamba is a benzoic acid derivative used as a broad-spectrum herbicide. Dicamba can be used to control the annual and perennial rose weeds in grain crops and highlands, to control brush and bracken in pastures as well as legumes and cacti. It kills broadleaf weeds both before and after they sprout. Dicamba takes effect through stimulating the outgrowth of plant, which causes the exhaustion of nutrients supplies and plant death. This is based on the nature of Dicamba, which is a synthetic mimic of natural auxin (a plant hormone used for simulating plant growth). Upon response to this kind of herbicide, the plant develops abnormalities such as leaf epinasty, leaf abscission, and growth inhibition of the root and shoots. Overall, the effects of auxinic herbicides can be divided into three consecutive phases in the plant: first, stimulation of abnormal growth and gene expression; second, inhibition of growth and physiological responses, such as stomatal closure; and third, senescence and cell death. Dicamba was introduced in the 1960s and is selective in cereals, corn (Zea mays), sugar cane (Saccharum spp.), asparagus (Asparagus officinalis), and turf for the pre- and post-emergence control of annual and perennial broadleaf weeds. Dicamba exhibits lowto- moderate persistence in most soils. See Table 10 for the nomenclature, chemical structure, and physical and chemical properties of dicamba.
• Uses: Selective, systemic preemergence and postemergence herbicide used to control both annual and perennial broad-leaved weeds, chickweed, mayweed and bindweed in cereals and other related crops. Dicamba is mainly used as an herbicide to control weeds, dock, bracken, and brush. Dicamba is frequently applied with other herbicides, including atrazine, glyphosate, imazethapyr, ioxynil, and mecoprop. Herbicide.

Technology Process of Dicamba

There total 58 articles about Dicamba which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.5%

2-methoxy-3,6-dichlorobenzaldehyde (27164-08-5) → 3,6-dichloro-O-anisic acid (1918-00-9,62610-39-3,89300-29-8)

Guidance literature:

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

Reference yield: 95.5%

2-bromo-3,6-dichlorobenzoic acid + sodium methylate (124-41-4) → 3,6-dichloro-O-anisic acid (1918-00-9,62610-39-3,89300-29-8)

Guidance literature:

In methanol; at 40 - 65 ℃; for 2h; Temperature;

Reference yield: 95.0%

methyl 3,6-dichloro-2-methoxybenzoate (6597-78-0) → 3,6-dichloro-O-anisic acid (1918-00-9,62610-39-3,89300-29-8)

Guidance literature:

With sodium hydroxide; In water;

upstream raw materials:

3,6-dichloro-2-hydroxybenzoic acid

1-Adamantanethiol

methyl 3,6-dichloro-2-methoxybenzoate

thiophenol

Downstream raw materials:

salicylic alcohol

methyl 3,6-dichloro-2-methoxybenzoate

methyl 2-methoxy-3,6-bis(phenylthio)benzoate

dicamba 2-nitrobenzyl ester

Refernces

• 1、 -. "Preparation method of dicamba". Paragraph 0014-0019. . Retrieved 2019/01/23.
• 2、 -. "A dicamba preparation method (by machine translation)". Paragraph 0041-0059. . Retrieved 2019/06/05.