2008-58-4

Basic information

• Product Name: 2,6-Dichlorobenzamide
• Synonyms: TIMTEC-BB SBB008056;LABOTEST-BB LT00455181;2,6-DICHLOROBENZAMIDE;ALDRIN PESTANAL (1,2,3,4,10,10-HEXA-CHLO;2,6-DICHLORBENZAMIDE;BENZAMIDE,2,6-DICHLORO-;2,6-BAM;2,6-Dichlorobenzamide,97%
• CAS NO: 2008-58-4
• Molecular Formula: C₇H₅Cl₂NO
• Molecular Weight: 190.03
• EINECS: 217-918-4
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Alpha sort;D;DAlphabetic;DIA - DIC;Pesticides&Metabolites
• Mol File: 2008-58-4.mol
• Article Data: 32

Chemical Properties

• Melting Point: 196-199 °C(lit.)
• Boiling Point: 266.482 °C at 760 mmHg
• Flash Point: 114.964 °C
• Appearance: White to brown-gray/Crystalline Powder
• Density: 1.2860 (rough estimate)
• Vapor Pressure: 0.00862mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Acetone (Slightly), Methanol (Slightly)
• PKA: 14.73±0.50(Predicted)
• Water Solubility: 2.7g/L(22.5 oC)
• BRN: 1869103
• CAS DataBase Reference: 2,6-Dichlorobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichlorobenzamide(2008-58-4)
• EPA Substance Registry System: 2,6-Dichlorobenzamide(2008-58-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 2008-58-4(Hazardous Substances Data)

Usage

Chemical Properties

white to brown-grey crystalline powder

Uses

2,6-Dichlorobenzamide is the persistent metabolite of herbicide 2,6-Dichlorobenzonitrile (D431945).

Definition

ChEBI: A member of the class of benzamides that is benzamide substituted by chloro groups at positions 2 and 6.

Metabolic pathway

Oral doses of DCB are excreted by rats as DCB, two monohydroxy-DCBs, 2-chloro-5-hydroxy-6- (methylthio)benzamide, and 2-chloro-5-hydroxy-6-[S- (N-acetyl)-cysteinyl]benzamide. Biliary excretion (33% of the dose), enterohepatic circulation, and intestinal microfloral metabolism are involved in the formation of 2-chloro-5-hydroxy-6-(methylthio)benzamide. The major route for the metabolism of DCB is the conjugation with glutathione in a process involving phenyl ring hydroxylation at the ortho position to the S-glutathionyl moiety. Two mechanisms can be processed for the formation of hydroxylated metabolites resulting from the epoxidation at the 2- and 3-positions of the phenyl ring (for the proposed mechanisms: see the text).

InChI:InChI=1/C7H5Cl2NO/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H2,10,11)

Upstream product

• 1194-65-6 2,6-dichloro-benzonitrile 
• 4659-45-4 2,6-Dichlorobenzoyl chloride 
• 7722-84-1 dihydrogen peroxide 
• 144-55-8 sodium hydrogencarbonate 
• 118-69-4 2,6-dichlorotoluene 
• 15258-73-8 2,6-dichlorobenzyl alcohol 
• 55-21-0 benzamide 
• 50-30-6 2,6-dichlorobenzoic acid 
• 6575-25-3 1,3-dichloro-2-ethynyl-benzene 
• 19393-92-1 1-bromo-2,6-dichlorobenzene 
• 3019-71-4 Trichloroacetyl isocyanate 
• 6575-28-6 (1E)-2,6-dichlorobenzaldehyde oxime 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 83-38-5 2,6-dichlorobenzaldehyde 

Downstream Products

• 1194-65-6 2,6-dichloro-benzonitrile 
• 345927-89-1 (2,6-Dichloro-phenyl)-(1,3-dihydroxy-1,3-dihydro-isoindol-2-yl)-methanone 
• 35367-09-0 N-(2,6-dichlorobenzoyl)-N'-(4-trifluoromethylphenyl)-urea 
• 35372-57-7 N-(2,6-dichlorobenzoyl)-N'-(3-trifluoromethylphenyl)urea 
• 59489-59-7 1-(2,6-Dichlorobenzoyl)-3-[6-methyl-5-(4-bromophenyl)-2-pyrazinyl]urea 
• 1238357-56-6 2,6-dichloro-trans-N-hex-1-enyl-benzamide 
• 67048-91-3 5-(2,6-dichloro-phenyl)-[1,3,4]oxathiazol-2-one 
• 42365-58-2 (2,6-dichlorophenyl)methanamine hydrochloride 
• 72617-88-0 1-(2,6-dichloro-benzoyl)-3-[6-(2,2,2-trifluoro-ethoxy)-pyridin-3-yl]-urea 

Relevant articles and documents

A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides

Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.

Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes

A straightforward Ni(ii)-catalyzed general strategy was developed for the ortho-halogenation of electron-deficient arenes with easily available halogenating reagents N-halosuccinimides (NXS; X = Br, Cl and I). The transformation was highly regioselective and a wide substrate scope and functional group tolerance were observed. This discovery could be of great significance for the selective halogenation of amides, benzoic esters and other substances with guiding groups. Mechanistic investigations were also described.

A halogenated benzamide compound preparation method (by machine translation)

The invention discloses a halogenated benzamide compound preparation method. The preparation method, comprises the following steps: adding the hydrogen peroxide to type I compounds, water and alkali are mixed to obtain a mixed solution of, shown in the following reaction; wherein X is halogen, n is 1, 2, 3, 4 or 5; states the type I compound charging capacity of at least 8 g, the hydrogen peroxide and the formula I compound in a molar ratio of 1:1 - 1.6: 1; the hydrogen peroxide addition time is 2 - 10 and H. The invention for the preparation of the water as the reaction solvent, to avoid the use of organic solvent, and in reducing the amount on the basis of raw materials, can still reach the higher yield and the product quality is good, the operation is simple, three wastes, economic effect is high, and is suitable for industrial production. (by machine translation)