2,6-Dichlorobenzonitrile Basic information
- Product Name:
- NIAGARA 5006
- AKOS BBS-00004654
- 2,6-DICHLOROBENZONITRILE, 1GM, NEAT
- DICHLOBENIL PESTANAL (2,6-DICHLORO- BENZ
- Product Categories:
- Building Blocks
- C6 to C7
- Chemical Synthesis
- Nitrogen Compounds
- Pharmaceutical Intermediates
- FINE Chemical & INTERMEDIATES
- Aromatic Nitriles
- Organic Building Blocks
- Mol File:
2,6-Dichlorobenzonitrile Chemical Properties
- Melting point:
- 143-146 °C(lit.)
- Boiling point:
- 270-275 °C
- 1.4980 (rough estimate)
- vapor pressure
- 0.14Pa at 25℃
- refractive index
- 1.6000 (estimate)
- Flash point:
- storage temp.
- Sealed in dry,Room Temperature
- White to Almost white
- Water Solubility
- 25 mg/L (25 ºC)
- 2.7 at 20℃
- CAS DataBase Reference
- 1194-65-6(CAS DataBase Reference)
- NIST Chemistry Reference
- 2,6-Dichlorobenzoic acid nitrile(1194-65-6)
- EPA Substance Registry System
- Dichlobenil (1194-65-6)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 3077 9/PG 3
- WGK Germany
- Hazard Note
- HS Code
- Hazardous Substances Data
- 1194-65-6(Hazardous Substances Data)
- LD50 in rats, mice (mg/kg): 2710, 6800 orally (Bailey, White)
- Language:English Provider:2,6-Dichlorobenzonitrile
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
2,6-Dichlorobenzonitrile Usage And Synthesis
Soil-applied herbicide used to control many annual and perennial broad-leaved weeds.
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.
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.
Synthetic Communications, 20, p. 2785, 1990 DOI: 10.1080/00397919008051490
Synthesis, p. 943, 1992 DOI: 10.1055/s-1992-26271
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.
Air & Water Reactions
Not soluble in water.
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.
SOLID: Harmful if swallowed.
Flammability and Explosibility
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.
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®
Biological. A cell suspension of Arthrobacter sp., isolated from a hydrosol, degraded
dichlobenil to 2,6-dichlorobenzamide (71% yield) and several unidentified water soluble
metabolites (Miyazaki et al., 1975). This microorganism was capable of rapidly degrading
dichlobenil in aerobic sediment-water suspensions and in enrichment cultures (Miyazaki
et al., 1975).
Soil. The major soil metabolite is 2,6-dichlorobenzamide which undergoes further degradation to form 2,6-dichlorobenzoic acid. The estimated half-lives ranged from 1 to 12 months (Hartley and Kidd, 1987). Under field conditions, dichlobenil persists from 2 to 12 months (Ashton and Monaco, 1991). The disappearance of dichlobenil from a hydrosol and pond water was primarily due to volatilization and biodegradation. The time required for 50 and 90% dissipation of the herbicide from a hydrosol were approximately 20 and 50 days, respectively (Rice et al., 1974). Dichlobenil has a high vapor pressure and volatilization should be an important process. Williams and Eagle (1979) found that the half-life of dichlobenil was 4 weeks in soil 4–8 weeks after application. After 1 year following application, the half-life increased to 1 year.
Plant. In plants, dichlobenil is transformed into glucose conjugates, insoluble residues and hydroxy products that are phytotoxic (Ashton and Monaco, 1991). These include three phytotoxic compounds, namely 2,6-dichlorobenzonitrile, 3-hydroxy-2,6-dichlorobenzonitrile and 4-hydroxy-2,6-dichlorobenzonitrile (Duke et al., 1991). Massini (1961) provided some evidence that dichlobenil is metabolized by plants. French dwarf beans, tomatoes, gherkin and oat plants were all exposed to a saturated atmosphere of dichlobenil at room temperature for 4 days. Most of the herbicide was absorbed and translocated by the plants in 3 days. After 6 days of exposure, bean seedlings were analyzed for residues using thinlayer plate chromatography. In addition to dichlobenil, another compound was found but it was not 2,6-dichlorobenzoic acid (Massini, 1963).
Surface Water. The time required for 50 and 90% dissipation of the herbicide from New York pond water was approximately 21 and 60 days, respectively (Rice et al., 1974).
Photolytic. When dichlobenil was irradiated in methanol with a 450-W mercury lamp and a Corex filter for 8 hours, o-chlorobenzonitrile and benzonitrile formed as the major and minor products, respectively (Plimmer, 1970).
Chemical/Physical. Dichlobenil is hydrolyzed, especially in the presence of alkali, to 2,6-dichlorobenzamide (Briggs and Dawson, 1970; Worthing and Hance, 1991). Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax and Lewis, 1987).
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,
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.
Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.]
2,6-Dichlorobenzonitrile Preparation Products And Raw materials
- 027-83850377 13720274133
- 010-82848833 400-666-7788
- 400-0066400 13621662912
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