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2,6-Dichlorobenzonitrile

2,6-Dichlorobenzonitrile
2,6-Dichlorobenzonitrile structure
CAS No.
1194-65-6
Chemical Name:
2,6-Dichlorobenzonitrile
Synonyms
H-133;h1313;H 1313;BARRIER;CASORON;2,4-Dbn;2,6-Dbn;prefixd;Casaron;Fydulan
CBNumber:
CB4159964
Molecular Formula:
C7H3Cl2N
Formula Weight:
172.01
MOL File:
1194-65-6.mol

2,6-Dichlorobenzonitrile Properties

Melting point:
143-146 °C(lit.)
Boiling point:
270-275 °C
Density 
1.4980 (rough estimate)
refractive index 
1.6000 (estimate)
Flash point:
270°C
storage temp. 
Sealed in dry,Room Temperature
form 
neat
Water Solubility 
25 mg/L (25 ºC)
Merck 
14,3042
BRN 
1909167
InChIKey
YOYAIZYFCNQIRF-UHFFFAOYSA-N
CAS DataBase Reference
1194-65-6(CAS DataBase Reference)
EWG's Food Scores
3
FDA UNII
N42NR4196R
NCI Dictionary of Cancer Terms
barrier
NIST Chemistry Reference
2,6-Dichlorobenzoic acid nitrile(1194-65-6)
EPA Substance Registry System
Dichlobenil (1194-65-6)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS09
Signal word  Warning
Hazard statements  H312-H411
Precautionary statements  P280h-P302+P352a-P312a-P321-P362+P364-P501a-P273-P280
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
Toxicity LD50 in rats, mice (mg/kg): 2710, 6800 orally (Bailey, White)

2,6-Dichlorobenzonitrile price More Price(5)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45431 Dichlobenil PESTANAL 1194-65-6 250mg $40.2 2021-03-22 Buy
Sigma-Aldrich D57558 2,6-Dichlorobenzonitrile 97% 1194-65-6 25g $56.5 2021-03-22 Buy
TCI Chemical D1137 2,6-Dichlorobenzonitrile >99.0%(GC) 1194-65-6 25g $26 2021-03-22 Buy
TCI Chemical D1137 2,6-Dichlorobenzonitrile >99.0%(GC) 1194-65-6 500g $256 2021-03-22 Buy
Alfa Aesar A14986 2,6-Dichlorobenzonitrile, 98% 1194-65-6 100g $126 2021-03-22 Buy

2,6-Dichlorobenzonitrile Chemical Properties,Uses,Production

Chemical Properties

white powder

Uses

Herbicide.

Uses

Soil-applied herbicide used to control many annual and perennial broad-leaved weeds.

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.

Agricultural Uses

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.

Trade name

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®

Environmental Fate

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).

Metabolic pathway

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.

Purification Methods

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

2,6-Dichlorobenzonitrile Preparation Products And Raw materials

Raw materials

Preparation Products


2,6-Dichlorobenzonitrile Suppliers

Global( 406)Suppliers
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View Lastest Price from 2,6-Dichlorobenzonitrile manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-18 2,6-Dichlorobenzonitrile
1194-65-6
US $10.00 / KG 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
2020-11-11 2,6-Dichlorobenzonitrile
1194-65-6
US $18.00 / KG 1KG 99 10000KG Longyan Tianhua Biological Technology Co., Ltd
2020-07-01 high quality 2,6-Dichlorobenzonitrile kf-wang(at)kf-chem.com
1194-65-6
US $10.00 / Kg/Drum 1g 99.8% 2000 Hebei Aicrowe Biotech Co., Ltd

2,6-Dichlorobenzonitrile Spectrum


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