2,6-дихлорбензонитрила

Химические свойства

2,6-Dichlorobenzonitrile [1194-65-6], 1- cyano-2,6-dichlorobenzene, Mr 172.02, mp 144.5 –146.5 ℃, is a colorless, crystalline substance. Its solubility in water is 10 ppm at 25℃. 2,6-Dichlorobenzonitrile is produced industrially by the ammoxidation of 2,6-dichlorotoluene. In addition the nitrile is obtained by oxidation or side-chain-chlorination of 2,6-dichlorotoluene via 2,6-dichlorobenzoic acid and 2,6-dichlorobenzaldehyde, respectively. 2,6-Dichlorobenzonitrile shows herbicidal activity (Casoron, Duphar) and is used in fruit and vine cultivation. It is also used as an intermediate in the production of 2,6-difluorobenzonitrile and of 2,6-dichlorothiobenzamide (Prefix, Shell) which shows herbicidal activity.

Использование

2,6-dichlorobenzonitrile in which Q-amino-G- chlorobenzonitrile is used as starting material. And it is used for the synthesis of diclofenac sodium oxacillin and guanabenz acetate.

Определение

ChEBI: A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide.

Общее описание

2,6-Dichlorobenzonitrile is a white solid dissolved or suspended in a water-emulsifiable liquid carrier. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Can cause illness by inhalation, skin absorption and/or ingestion. Used as a herbicide.

Реакции воздуха и воды

Not soluble in water.

Профиль реактивности

A halogenated nitrile. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Угроза здоровью

SOLID: Harmful if swallowed.

Пожароопасность

Not flammable.

Сельскохозяйственное использование

Herbicide: Dichlobenil is a herbicide used on cranberry bogs, dichondra, ornamentals, blackberry, raspberry, and blueberry fields, apple, pear, filbert and cherry orchards, vineyards, hybrid poplar-cottonwood plantations, and rights-of-way to control weeds; and sewers to remove roots. It acts on dandelion, prickly oxtongue (pre-emergence), and tree roots. Not approved for use in EU countries. Actively registered in the U.S.

Торговое название

BARRIER®; BH Prefix D®; CARSORON®; CASORON® 133; CARSORON® G; CARSORON® G4; CARSORON® G20-SR; CODE H 133®; DECABANE®; DU-SPREX®; DYCLOMEC®; FYDULAN; FYDUMAS; FYDUSIT; H 133®; H 1313®; NIA 5996®; NIAGARA® 5006; NIAGARA 5,996; NOROSAC®; PREFIX D®

Метаболический путь

Twelve metabolites are isolated from either urine or bile from either rats (11 metabolites) or goats (seven metabolites) given single oral doses of 14C-labeled 2,6-dichlorobenzonitrile (DCBN). Five of these metabolites are also excreted in urine from rats dosed orally with 2,6-dichlorothiobenzamide (DCTBA) which is an acid amide analog. All metabolites from either DCBN or DCTBA are benzonitriles with the following ring substituents: Cl2, OH (three isomers); Cl2, (OH)2; Cl, (OH)2; Cl, OH, SH; Cl, OH, SCH3; SOCH3, OH; Cl2, S-(N-acetyl)cysteine; Cl, S-(N-acetyl)cysteine; Cl, OH, S-(N-acetyl)cysteine.
The thiobenzamide moiety of DCTBA is converted to the nitrile in all extracted urinary metabolites. No hydrolysis of the nitrile in DCBN to either amide or an acid is detected. Urine is the major route for excretion; however, enterohepatic circulation occurs.

Методы очистки

Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.]