ContaminantDB: 2,6-Dichlorobenzonitrile

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (42)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:28 UTC

Update Date

2026-03-26 20:09:39 UTC

Accession Number

CHEM001457

Identification

Common Name

2,6-Dichlorobenzonitrile

Class

Small Molecule

Description

2,6-Dichlorobenzonitrile is a chemical compound of cyanide and a herbicide. (3)

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Cyanide Compound
Household Toxin
Nitrile
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,6-DBN	ChEBI
2,6-Dichlorobenzoic acid nitrile	ChEBI
2,6-Dichlorophenyl cyanide	ChEBI
DBN	ChEBI
DCB	ChEBI
Dichlobanil	ChEBI
Dichlobenil	ChEBI
2,6-Dichlorobenzoate nitrile	Generator

Chemical Formula

C₇H₃Cl₂N

Average Molecular Mass

172.011 g/mol

Monoisotopic Mass

170.964 g/mol

CAS Registry Number

1194-65-6

IUPAC Name

2,6-dichlorobenzonitrile

Traditional Name

prefix D

SMILES

ClC1=CC=CC(Cl)=C1C#N

InChI Identifier

InChI=1S/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H

InChI Key

YOYAIZYFCNQIRF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

1,3-dichlorobenzene
Benzonitrile
Aryl halide
Aryl chloride
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

nitrile (CHEBI:943 )
dichlorobenzene (CHEBI:943 )
Nitrile herbicides (C11040 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

cellulose synthesis inhibitor

Chemical Roles

cellulose synthesis inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	144.5°C
Boiling Point	Not Available
Solubility	0.0146 mg/mL at 20°C [TOMLIN,C (1997)]

Predicted Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.04	ChemAxon
logS	-3.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.39 m³·mol⁻¹	ChemAxon
Polarizability	15.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-2900000000-c1396a00c4ee1d09e8b0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0ik9-0900000000-148f4a8ae71ac6762754	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03di-0900000000-987df8d230f2ba206d67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-03di-0900000000-4d7441c2671d994fd330	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0229-0900000000-e1ec3638482af968c3ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-0900000000-b9b82395138a1d19c156	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-0900000000-37e1d560136079d29a26	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0229-0900000000-eb64f0dd9c8ba22ccb4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0900000000-ead85b54a10216ce57c8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-0900000000-02fceddcba8b2d6114a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-db76800c34775d8c7ef5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-db76800c34775d8c7ef5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900000000-053fc33c46f31bba45b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-662a68714490ecda1f14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-662a68714490ecda1f14	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-1900000000-0a6f290ca8e7a6844514	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-e5d1b8351808c2116a80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0900000000-e5d1b8351808c2116a80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900000000-257b3c4a8551bbde3f05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-3a7170fc9911f2615939	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0900000000-3a7170fc9911f2615939	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-3a7170fc9911f2615939	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-2900000000-09706bc36ecbfb4bd95f	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (1) ; inhalation (1) ; dermal (1)

Mechanism of Toxicity

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (2)

Metabolism

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (1)

Toxicity Values

LD50: 3160 mg/kg over 48 hours (Oral, Rat) (6) LD50: 707 mg/kg over 48 hours (Intraperitoneal, Mouse) (6) LC50: >250 mg/m3 over 4 hours (Inhalation, Rat) (5)

Lethal Dose

217 to 300 milligrams for an adult human (cyanide salts). (4)

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

2,6-Dichlorobenzonitrile is a herbicide. (3)

Minimum Risk Level

Not Available

Health Effects

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (1, 2)

Symptoms

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (1, 2)

Treatment

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (2)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0245512

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID