2,6-Dichlorobenzonitrile CAS 1194-65-6
Introduction：Basic information about 2,6-Dichlorobenzonitrile CAS 1194-65-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2,6-Dichlorobenzonitrile Basic information
| Product Name: | 2,6-Dichlorobenzonitrile |
| Synonyms: | SILBENIL;NIAGARA 5006;2,6-DICHLOROBENZONITRILE;AKOS BBS-00004654;2,6-DICHLOROBENZONIT;2,6-DCBN;2,6-DICHLOROBENZONITRILE, 1GM, NEAT;DICHLOBENIL PESTANAL (2,6-DICHLORO- BENZ |
| CAS: | 1194-65-6 |
| MF: | C7H3Cl2N |
| MW: | 172.01 |
| EINECS: | 214-787-5 |
| Product Categories: | intermediate;Building Blocks;C6 to C7;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks;Nitriles;FINE Chemical & INTERMEDIATES;Aromatic Nitriles;Pharmaceutical Intermediates;OLED |
| Mol File: | 1194-65-6.mol |
2,6-Dichlorobenzonitrile Chemical Properties
| Melting point | 143-146 °C(lit.) |
| Boiling point | 270-275 °C |
| density | 1.4980 (rough estimate) |
| vapor pressure | 0.14Pa at 25℃ |
| refractive index | 1.6000 (estimate) |
| Fp | 270°C |
| storage temp. | Sealed in dry,Room Temperature |
| form | powder |
| color | White to Almost white |
| Water Solubility | 25 mg/L (25 ºC) |
| Merck | 14,3042 |
| BRN | 1909167 |
| Major Application | agriculture environmental |
| InChI | 1S/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H |
| InChIKey | YOYAIZYFCNQIRF-UHFFFAOYSA-N |
| SMILES | Clc1cccc(Cl)c1C#N |
| LogP | 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) |
Safety Information
| Hazard Codes | Xn,N,T,Xi |
| Risk Statements | 21-51/53 |
| Safety Statements | 36/37-61 |
| RIDADR | UN 3077 9/PG 3 |
| WGK Germany | 2 |
| RTECS | DI3500000 |
| Hazard Note | Irritant/Toxic |
| HazardClass | 9 |
| PackingGroup | III |
| HS Code | 29269090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Dermal Aquatic Chronic 2 |
| Hazardous Substances Data | 1194-65-6(Hazardous Substances Data) |
| Toxicity | LD50 in rats, mice (mg/kg): 2710, 6800 orally (Bailey, White) |
| Chemical Properties | 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. |
| Uses | Herbicide. |
| Uses | Soil-applied herbicide used to control many annual and perennial broad-leavedweeds. |
| Uses | 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. |
| Definition | 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. |
| Synthesis Reference(s) | Synthetic Communications, 20, p. 2785, 1990 DOI: 10.1080/00397919008051490 Synthesis, p. 943, 1992 DOI: 10.1055/s-1992-26271 |
| General Description | 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. |
| Reactivity Profile | 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. |
| Health Hazard | SOLID: Harmful if swallowed. |
| Fire Hazard | Not flammable. |
| Flammability and Explosibility | Non flammable |
| Agricultural Uses | Herbicide: Dichlobenil is a herbicide used on cranberry bogs,dichondra, ornamentals, blackberry, raspberry, and blueberryfields, apple, pear, filbert and cherry orchards,vineyards, hybrid poplar-cottonwood plantations, andrights-of-way to control weeds; and sewers to removeroots. It acts on dandelion, prickly oxtongue (pre-emergence),and tree roots. Not approved for use in EU countries.Actively registered in the U.S. |
| Trade name | BARRIER®; BH Prefix D®;CARSORON®; CASORON® 133; CARSORON® G;CARSORON® G4; CARSORON® G20-SR; CODE H133®; DECABANE®; DU-SPREX®; DYCLOMEC®;FYDULAN; FYDUMAS; FYDUSIT; H 133®; H 1313®;NIA 5996®; NIAGARA® 5006; NIAGARA 5,996;NOROSAC®; PREFIX D® |
| Environmental Fate | Biological. A cell suspension of Arthrobacter sp., isolated from a hydrosol, degradeddichlobenil to 2,6-dichlorobenzamide (71% yield) and several unidentified water solublemetabolites (Miyazaki et al., 1975). This microorganism was capable of rapidly degradingdichlobenil in aerobic sediment-water suspensions and in enrichment cultures (Miyazakiet al., 1975). Soil. The major soil metabolite is 2,6-dichlorobenzamide which undergoes furtherdegradation to form 2,6-dichlorobenzoic acid. The estimated half-lives ranged from 1 to12 months (Hartley and Kidd, 1987). Under field conditions, dichlobenil persists from 2to 12 months (Ashton and Monaco, 1991). The disappearance of dichlobenil from ahydrosol and pond water was primarily due to volatilization and biodegradation. The timerequired for 50 and 90% dissipation of the herbicide from a hydrosol were approximately20 and 50 days, respectively (Rice et al., 1974). Dichlobenil has a high vapor pressureand volatilization should be an important process. Williams and Eagle (1979) found thatthe half-life of dichlobenil was 4 weeks in soil 4–8 weeks after application. After 1 yearfollowing application, the half-life increased to 1 year. Plant. In plants, dichlobenil is transformed into glucose conjugates, insoluble residuesand hydroxy products that are phytotoxic (Ashton and Monaco, 1991). These include threephytotoxic compounds, namely 2,6-dichlorobenzonitrile, 3-hydroxy-2,6-dichlorobenzonitrileand 4-hydroxy-2,6-dichlorobenzonitrile (Duke et al., 1991). Massini (1961) providedsome 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 roomtemperature for 4 days. Most of the herbicide was absorbed and translocated by the plantsin 3 days. After 6 days of exposure, bean seedlings were analyzed for residues using thinlayerplate chromatography. In addition to dichlobenil, another compound was found butit was not 2,6-dichlorobenzoic acid (Massini, 1963). Surface Water. The time required for 50 and 90% dissipation of the herbicide fromNew 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 lampand a Corex filter for 8 hours, o-chlorobenzonitrile and benzonitrile formed as the majorand minor products, respectively (Plimmer, 1970). Chemical/Physical. Dichlobenil is hydrolyzed, especially in the presence of alkali, to2,6-dichlorobenzamide (Briggs and Dawson, 1970; Worthing and Hance, 1991).Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Saxand Lewis, 1987). |
| Metabolic pathway | Twelve metabolites are isolated from either urine orbile from either rats (11 metabolites) or goats (sevenmetabolites) given single oral doses of 14C-labeled2,6-dichlorobenzonitrile (DCBN). Five of thesemetabolites are also excreted in urine from rats dosedorally with 2,6-dichlorothiobenzamide (DCTBA) whichis an acid amide analog. All metabolites from either DCBN or DCTBA are benzonitriles with the followingring 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 convertedto the nitrile in all extracted urinary metabolites. Nohydrolysis of the nitrile in DCBN to either amide or anacid is detected. Urine is the major route for excretion;however, enterohepatic circulation occurs. |
| Purification Methods | Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.] |
2,6-Dichlorobenzonitrile Preparation Products And Raw materials
| Raw materials | 1,2-Dichlorobenzene-->Dehydrolyzing agent-->2,6-Dichlorotoluene-->2,6-Dichloroaniline-->2,6-Dichlorobenzaldoxime-->2,6-Dichlorobenzal chloride |
| Preparation Products | Chlorfluazuron-->2,6-Difluorobenzonitrile-->Diflubenzuron-->Teflubenzuron-->2,6-BIS(2,2,2-TRIFLUOROETHOXY)BENZONITRILE-->2',6'-Dichloroacetophenone-->2,6-Dichlorobenzaldehyde |
