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 
• 3714-77-0 2,6-dichlorobenzaldoxime 
• 83-38-5 2,6-dichlorobenzaldehyde 
• 25185-95-9 2,6-dichlorobenzaldoxime 
• 144-55-8 sodium hydrogencarbonate 
• 6575-28-6 (1E)-2,6-dichlorobenzaldehyde oxime 
• 19393-92-1 1-bromo-2,6-dichlorobenzene 
• 3019-71-4 Trichloroacetyl isocyanate 
• 118-69-4 2,6-dichlorotoluene 
• 6575-25-3 1,3-dichloro-2-ethynyl-benzene 
• 50-30-6 2,6-dichlorobenzoic acid 
• 55-21-0 benzamide 

Downstream Products

• 1194-65-6 2,6-dichloro-benzonitrile 
• 67048-91-3 5-(2,6-dichloro-phenyl)-[1,3,4]oxathiazol-2-one 
• 35377-49-2 2,6-dichlorobenzoyl isocyanate 
• 35409-97-3 N-(2,6-dichlorobenzoyl)-N'-(4-chlorophenyl)-urea 
• 35372-56-6 N-(2,6-dichlorobenzoyl)-N'-(4-fluorophenyl)urea 
• 35366-75-7 1-(2,6-Dichloro-benzoyl)-3-(3-fluoro-phenyl)-urea 
• 345927-89-1 (2,6-Dichloro-phenyl)-(1,3-dihydroxy-1,3-dihydro-isoindol-2-yl)-methanone 
• 116800-83-0 N-(Bis-methylsulfanyl-methylene)-2,6-dichloro-benzamide 
• 119448-94-1 (2,6-Dichloro-benzoyl)-dithiocarbamic acid methyl ester 
• 50822-24-7 1-(2,6-Dichloro-benzoyl)-3-(2-trifluoromethyl-phenyl)-urea 
• 608-31-1 2,6-Dichloroaniline 
• 960249-95-0 1,1-dimethylethyl [(2.6-dichlorophenyl)carbonyl]carbamate 
• 92207-23-3 1-(2,6-dichlorobenzoyl)-3-(2,4,6-trichlorophenyl)-urea 
• 139391-97-2 1-(2,6-Dichloro-benzoyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-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.

Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring

Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.