ContaminantDB: 1,4-Dichlorobenzene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (40)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:11 UTC

Update Date

2026-03-31 19:41:43 UTC

Accession Number

CHEM000146

Identification

Common Name

1,4-Dichlorobenzene

Class

Small Molecule

Description

1,4-Dichlorobenzene (p-DCB, para-dichlorobenzene) is an organic compound with the formula C6H4Cl2. This colorless solid has a strong odor. In terms of its structure, the molecule consists of two chlorine atoms substituted for hydrogen at opposing sites on a benzene ring. p-DCB is used a pesticide and a deodorant, most familiarly in mothballs in which it is a replacement for the more traditional naphthalene. p-DCB is also used as a precursor in the production of the polymer poly(p-phenylene sulfide). Under California's Proposition 65, p-DCB is listed as known to the State to cause cancer.[8] A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing p-DCB has been identified.

Contaminant Sources

Clean Air Act Chemicals
HMDB Contaminants - Feces
HPV EPA Chemicals
IARC Carcinogens Group 2B
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Household Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Lachrymator
Metabolite
Organic Compound
Organochloride
Pesticide
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
p-Chlorophenyl chloride	ChEBI
p-Dichlorbenzol	ChEBI
PARA	ChEBI
Paradichlorbenzol	ChEBI
Paradichlorobenzene	ChEBI
PDCB	ChEBI
1, 4-Dichlorobenzene	HMDB
1,4-Chlorobenzene	HMDB
1,4-Dichloorbenzeen	HMDB
1,4-Dichlor-benzol	HMDB
1,4-Dichloro-benzene	HMDB
1,4-Dichlorobenzene (acd/name 4.0)	HMDB
1,4-Diclorobenzene	HMDB
Di-chloricide	HMDB
Dichlorobenzene	HMDB
Dichlorobenzene, p-, solid	HMDB
Dichlorobenzene, para	HMDB
Dichlorocide	HMDB
Evola	HMDB
Globol	HMDB
Kaydox	HMDB
p-Dichloorbenzeen	HMDB
p-Dichlorbenzene	HMDB
p-Dichloro-benzene	HMDB
p-Dichlorobenzol	HMDB
p-Diclorobenzene	HMDB
Para crystals	HMDB
Para-dichlorobenzene	HMDB
Paracide	HMDB
Paradi	HMDB
Paradichlorobenzol	HMDB
Paradow	HMDB
Paramoth	HMDB
Paranuggets	HMDB
Parazene	HMDB
PDB	HMDB
Persia-perazol	HMDB
Rcra waste number u070	HMDB
Rcra waste number u071	HMDB
Rcra waste number u072	HMDB
Santochlor	HMDB
4-Dichlorobenzene	HMDB
P-Dichlorobenzene	ChEBI

Chemical Formula

C₆H₄Cl₂

Average Molecular Mass

147.002 g/mol

Monoisotopic Mass

145.969 g/mol

CAS Registry Number

106-46-7

IUPAC Name

1,4-dichlorobenzene

Traditional Name

paradi

SMILES

ClC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C6H4Cl2/c7-5-1-2-6(8)4-3-5/h1-4H

InChI Key

OCJBOOLMMGQPQU-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

1,4-dichlorobenzene
Aryl halide
Aryl chloride
Hydrocarbon derivative
Organochloride
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dichlorobenzene (CHEBI:28618 )
Fumigant (C07092 )
a chloroaromatic compound (14-DICHLOROBENZENE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

insecticide

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	52.7°C
Boiling Point	Not Available
Solubility	0.0813 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.46	ALOGPS
logP	3.18	ChemAxon
logS	-3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.67 m³·mol⁻¹	ChemAxon
Polarizability	13.32 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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-4900000000-73f255545f9196d189ad	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2900000000-983d7c8ebc0e5f138b53	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-4900000000-33e4c1cd3b8d393493c5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2900000000-324c6fc09e913a17becf	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-4900000000-73f255545f9196d189ad	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2900000000-983d7c8ebc0e5f138b53	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-4900000000-33e4c1cd3b8d393493c5	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0002-2900000000-324c6fc09e913a17becf	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-3900000000-20b22c60107af8d61659	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-29f82f20a2b88e992b2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-79725bc4bbbb391c3305	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0900000000-92754602e0e625430820	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-40127a320d53fe67229c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-40127a320d53fe67229c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1900000000-30520308036afaac23c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-49a9c8d124e4edc0341a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-49a9c8d124e4edc0341a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1900000000-2a065e692fdf9b188915	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-a9d440f8a98d9647aefb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-a9d440f8a98d9647aefb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-4900000000-cd14a666e852017d58a1	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-3900000000-12fe56062da20e240f5c	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (6) ; oral (6) ; dermal (6) ; eye contact (6)

Mechanism of Toxicity

The hepatotoxicity and nephrotoxicity observed in laboratory animals are likely due to the formation of toxic intermediates formed while converting 1,4-DCB to 2,5-dichlorophenol by cytochrome P-450, or by depletion of GSH at higher doses of 1,4-DCB, or both. (5)

Metabolism

Absorption of 1,4-DCB is rapid and essentially complete following inhalation or oral exposure. It is distributed throughout the body, preferentially to the fat tissue and organ-specific sites within the body, following the order: adipose > kidney > liver > blood. 1,4-DCB is initially metabolized by cytochrome P-450 enzymes, specifically P4502E1, to an active epoxide followed by hydrolysis to 2,5-dichlorophenol, which may be further oxidized to dichlorocatechols, or possibly a dichlorohydroquinone. More often, it might be conjugated to sulfate, or to form the glucuronide, or mercapturic acid; conjugation occurs extensively, with virtually no unconjugated metabolites reported in the available studies. Metabolism is believed to occur mainly in the liver, but may occur at lower levels in other tissues, such as the kidney or lung. 1,4-DCB is eliminated almost exclusively in the urine, primarily as conjugates of 2,5-dichlorophenol. (5)

Toxicity Values

LD50: >6000 mg/kg/day (Dermal, Rat) (5) LD50: 500 mg/kg/day (Oral, Rat) (5)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (3)

Uses/Sources

1,4-DCB is used a pesticide and a deodorant, most famously in mothballs in which it is a replacement for the more traditional naphthalene. 1,4-DCB is also used as a precursor in the production of the polymer poly(p-phenylene sulfide). 1,4-DCB also is used to make deodorant blocks used in garbage cans and restrooms, and to help control odors in animal-holding facilities. 1,4-DCB has been used as an insecticide on fruit and as an agent to control mold and mildew growth on tobacco seeds, leather, and some fabrics. Recently, using 1,4-DCB to make resins has become very important. Exposure may result from breathing vapors from 1,4-DCB products, drinking contaminated water or eating contaminated food (However, the levels of p-DCB in foods are generally low), and eye exposure. (4, 5, 6)

Minimum Risk Level

Acute Inhalation: 2 ppm (5) Intermediate Inhalation: 0.2 ppm (5) Chronic Inhalation: 0.01 ppm (5) Intermediate Oral: 0.07 mg/kg/day (Rodent) (5) Chronic Oral: 0.07 mg/kg/day (Rat) (5)

Health Effects

Prolonged exposure to high concentration of 1,4-DCB may cause weakness, dizziness, loss of weight, liver injury. Chronic (months to years) ingestion of 1,4-DCB products can provoque skin blotches and problems with red blood cells, such as anemia. There is an indication that 1,4-DCB can affect the development of the nervous system after birth. 1,4-DCB is possibly a human carcinogen. (5, 8)

Symptoms

Burning sensation, cough, drowsiness, headache, nausea, shortness of breath, and vomiting can follow inhalation or ingestion of 1,4-DCB. Moreover, its ingestion can cause diarrhoea. Eye exposure can lead to redness and pain of the contact surface. Vapors may cause irritation to skin, nose, throat, and eyes. Solid p-dichlorobenzene has very little effect on the skin. (5, 8)

Treatment

Administer charcoal as a slurry (240 mL water/30 g charcoal). Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. After eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact, remove contaminated clothing and wash exposed area thoroughly with soap and water. In any case, a physician may need to examine the area if irritation or pain persists. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041971

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID