| Identification | More | [Name]
1,4-Dichlorobenzene | [CAS]
106-46-7 | [Synonyms]
1,4-DICHLOROBENZENE
DI-CHLORICIDE
DI-CHLORICIDE(R)
'LGC' (1115)
PARACIDE(R)
PARA DICHLOROBENZENE
PARAMOTH
PARAZENE
PDB
PDB(R)
SANTOCHLOR(R) 20
U.N. 1592
1,4-chlorobenzene
1,4-dcb
1,4-Dichloorbenzeen
1,4-Dichlorbenzol
1,4-Dichlor-benzol
1,4-dichloro-benzen
1,4-Dichlorobenzene paste
1,4-Diclorobenzene | [EINECS(EC#)]
203-400-5 | [Molecular Formula]
C6H4Cl2 | [MDL Number]
MFCD00000604 | [Molecular Weight]
147 | [MOL File]
106-46-7.mol |
| Chemical Properties | Back Directory | [Appearance]
There are three isomeric forms of dichlorobenzene (DCB):
m-DCB is a flammable liquid and vapor. | [Melting point ]
52-54 °C (lit.) | [Boiling point ]
173 °C (lit.) | [density ]
1.241 g/mL at 25 °C(lit.)
| [vapor density ]
5.07 (vs air)
| [vapor pressure ]
1.03 mm Hg ( 25 °C)
| [refractive index ]
1.5434 | [Fp ]
150 °F
| [storage temp. ]
0-6°C
| [solubility ]
0.08g/l | [form ]
Crystals | [color ]
White | [Specific Gravity]
1.2417 | [Odor]
Aromatic. | [PH]
7 (0.06g/l, H2O, 20℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, aluminium and its alloys, some plastics. | [explosive limit]
1.7-5.9%(V) | [Water Solubility ]
insoluble | [Merck ]
14,3057 | [BRN ]
1680023 | [Henry's Law Constant]
1.88 at 25 °C (continuous flow sparger, Sproule et al., 1991) | [Dielectric constant]
2.8（53℃） | [Exposure limits]
TLV-TWA 75 ppm (～450 mg/m3) (MSHA,
OSHA, and NIOSH); IDLH 1000 ppm
(NIOSH). | [LogP]
3.37 at 25℃ and pH7 | [CAS DataBase Reference]
106-46-7(CAS DataBase Reference) | [IARC]
2B (Vol. Sup 7, 73) 1999 | [NIST Chemistry Reference]
Benzene, 1,4-dichloro-(106-46-7) | [EPA Substance Registry System]
106-46-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,T,F | [Risk Statements ]
R36:Irritating to the eyes.
R40:Limited evidence of a carcinogenic effect.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S46:If swallowed, seek medical advice immediately and show this container or label .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [RTECS ]
CZ4550000
| [Autoignition Temperature]
>500 °C | [TSCA ]
Yes | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29036100 | [Safety Profile]
Confirmed carcinogen
with experimental carcinogenic data. An experimental teratogen. A human poison by
an unspecified route. Moderately toxic to
humans by ingestion. Moderately toxic
experimentally by ingestion, subcutaneous,
and intraperitoneal routes. Other
experimental reproductive effects. Human
systemic effects by ingestion: unspecified
changes in the eyes, lungs, thorax and
respiration, and decreased motihty or
constipation. Can cause liver injury in
humans. A human eye irritant. Mutation
data reported. A fumigant. Flammable liquid
when exposed to heat, flame, or oxidizers.
Dangerous; can react vigorously with
oxidizing materials. To fight fire, use water,
foam, CO2, dry chemical. When heated to
decomposition it emits toxic fumes of Cl-.
See also CHLORINATED
HYDROCARBONS, AROMATIC. | [Hazardous Substances Data]
106-46-7(Hazardous Substances Data) | [Toxicity]
LD50 in male, female rats (mg/kg): 3863, 3790 orally; >6000, >6000 dermally (Gaines, Linder) | [IDLA]
150 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Benzene-->Chlorine-->1,2-Dichlorobenzene-->1,3-Dichlorobenzene-->p-Dichlorobenzene-->Antimony-->DICHLOROBENZENE MIXTURE | [Preparation Products]
2,5-Dichloronitrobenzene-->POLY(1,4-PHENYLENE SULFIDE)-->2,2',3,5'-TETRACHLOROBIPHENYL-->1,4-Bis(dimethylsilyl)benzene-->2-Bromo-1,4-dichlorobenzene-->2,5-Dichlorobenzaldehyde-->(4-CHLOROPHENYLTHIO)ACETONE-->1,4-DICYCLOHEXYLBENZENE-->1 4-BIS(DIPHENYLAMINO)BENZENE-->2,3-Dichlorobenzoic acid |
| Hazard Information | Back Directory | [General Description]
A white colored liquid with the odor of moth balls. Denser than water and insoluble in water. Flash point below 200°F. Used as a moth repellent, to make other chemicals, as a fumigant, and for many other uses. | [Reactivity Profile]
P-DICHLOROBENZENE(106-46-7) is incompatible with oxidizing agents. P-DICHLOROBENZENE(106-46-7) is also incompatible with aluminum and its alloys. P-DICHLOROBENZENE(106-46-7) liquefies when mixed with camphor, phenol and salol. P-DICHLOROBENZENE(106-46-7) will attack some forms of plastics, rubber and coatings. . | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
INHALATION: irritation of upper respiratory tract; over-exposure may cause depression and injury to liver and kidney. EYE CONTACT: pain and mild irritation. | [Potential Exposure]
The major uses of o-DCB are as
a process solvent in the manufacturing of toluene diisocyanate and as an intermediate in the synthesis of dyestuffs,
herbicides, and degreasers. p-Dichlorbenzene is used
primarily as a moth repellant, a mildew control agent;
space deodorant; and in insecticides, which accounts for
90% of the total production of this isomer. Information is
not available concerning the production and use of m-DCB.
However, it may occur as a contaminant of o-or p-DCB
formulations. Both o-and p-isomers are produced almost
entirely as by-products during the production of
monochlorobenzene | [Fire Hazard]
Special Hazards of Combustion Products: Vapors are irritating. Toxic chlorine, hydrogen chloride, and phosgene gases may be generated in fires. | [First aid]
If this chemical gets into the eyes, remove
any contact lenses at once and irrigate immediately for
at least 15 minutes, occasionally lifting upper and lower
lids. Seek medical attention immediately. If this chemical
contacts the skin, remove contaminated clothing and wash
immediately with soap and water. Seek medical attention
immediately. If this chemical has been inhaled, remove
from exposure, begin rescue breathing (using universal
precautions, including resuscitation mask) if breathing
has stopped and CPR if heart action has stopped. Transfer
promptly to a medical facility. When this chemical
has been swallowed, get medical attention. Give large
quantities of water and induce vomiting. Do not make
an unconscious person vomit | [Shipping]
m-DCB: UN2810 Toxic liquids, organic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials,
Technical Name Required. United States DOT Regulated
Marine Pollutant. UN3077 Environmentally hazardous
substances, solis, n.o.s., Hazard class: 9; Labels:
9-Miscellaneous hazardous material, Technical NameRequired. UN3082 Environmentally hazardous substances,
liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required | [Incompatibilities]
For o-DCB and m-DCB: acid fumes,
chlorides, strong oxidizers; hot aluminum, or aluminum
alloys. For p-DCB: Strong oxidizers; although, incompatibilities for this chemical may also include other materials
listed for o-DCB. | [Description]
Paradichlorobenzene, or PDB, also commonly known as mothballs, are white, volatile crystals with a penetrating odor. Boiling point is 345°F (173°C), flash point is 150°F (65.6°C), and the melting point is 127°F (52°C). PDB is insoluble in water and has a specific gravity of 1.5, which is heavier than water. Vapor density is 5.1, which is heavier than air. In addition to being flammable, it is also toxic by ingestion and an irritant to the eyes, with a TLV of 75 ppm in air. The four-digit UN identification number is 1592. The NFPA 704 designation for PDB is health 2, flammability 2, and reactivity 0. The primary uses are as a moth repellent, a general insecticide, a soil fumigant, and in dyes. | [Chemical Properties]
colourless or white crystals | [Chemical Properties]
There are three isomeric forms of dichlorobenzene (DCB):
m-DCB is a flammable liquid and vapor. | [Waste Disposal]
Incineration, preferably
after mixing with another combustible fuel. Care must be
exercised to assure complete combustion to prevent
the formation of phosgene. An acid scrubber is necessary
to remove the halo acids produced. Consult with
environmental regulatory agencies for guidance on
acceptable disposal practices. Generators of waste containing
this contaminant (≥100 kg/mo) must conform with EPA
regulations governing storage, transportation, treatment, and
waste disposal | [Physical properties]
Colorless to white crystals with a penetrating, sweet, mothball or almond-like odor. At 40 °C, the
average odor threshold concentration and the lowest concentration at which an odor was detected
were 18 and 4.5 μg/L, respectively. Similarly, at 25 °C, the average taste threshold concentration
and the lowest concentration at which a taste was detected were 32 and 11 μg/L, respectively
(Young et al., 1996). A detection odor threshold concentration of 73 μg/m3 (121 ppbv) was
reported by Punter (1983). | [Application]
1,4-Dichlorobenzene is used as a fumigantand as an insecticide. For domestic use against clothes moths; as space deodorant in room deodorizers, toilet bowl blocks and diaper pail deodorizers. Intermediate in production of plastics for electronic components. | [Uses]
1,4-Dichlorobenzene is used as a fumigantand as an insecticide. | [Uses]
Insecticidal fumigant. For domestic use against clothes moths; as space deodorant in room deodorizers, toilet bowl blocks and diaper pail deodorizers. Intermediate in production of plastics for electronic components. | [Uses]
The compound 1,4-dichlorobenzene is most commonly referred to as para-DCB or p-DCB. It is widely used as a moth killer, in space deodorizers, and in the production of polyphenylene sulfide. It is also used in the manufacture of certain resins, in the pharmaceutical industry, and as a general insecticide in farming. At room temperature, 1,4- dichlorobenzene is a white or colorless crystalline solid with a characteristic penetrating odor. When exposed to air, it is slowly transformed from its solid state into a vapor; the released vapor then acts as a deodorizer and insect killer. It is practically insoluble in water and is soluble in alcohol, acetone, ether, chloroform, carbon disulfide, and benzene. Its chemical formula is C6H4Cl2.
There is limited evidence that 1,4-dichlorobenzene can damage a developing fetus. Exposure can damage the lungs, liver, kidneys, and blood cells, causing anemia; it can also cause swelling of the eyes, hands, and feet. It can damage the nervous system, causing weakness, trembling, and numbness in the arms and legs. It may cause a skin allergy, which when developed can cause itching and a skin rash. Higher levels of the chemical in air, such as the levels that are sometimes associated with industrial exposure, can cause headaches, nausea, clumsiness, slurred speech, and dizziness. Levels that would result in death would be associated with an odor so intense that it would be very unpleasant, if not intolerable, and would serve as a danger warning. In industrial situations, workers exposed to 1,4- dichlorobenzene at high levels are usually directed to wear respirators. Workers involved in the production of the chemical may be exposed to concentrations significantly higher than those encountered by the general population. High exposure levels may result from some consumer products of moth repellents and room deodorizers. Approximately 95% of the environmental release of 1,4- dichlorobenzene occurs during its use, rather than during its manufacture or processing. | [Definition]
ChEBI: A dichlorobenzene carrying chloro groups at positions 1 and 4. | [Definition]
dichlorobenzene: Any one of threeisomeric liquid aromatic compounds,C6H4Cl2. 1,2-Dichlorobenzene (b.p.179°C) and 1,4-dichlorobenzene (b.p.174°C) are made by chlorinatingbenzene with an iron catalyst andseparating the mixed isomers byfractional distillation; 1,3-dichlorobenzene(b.p. 172°C) is made fromone of the other two by catalytic isomerization.The 1,2 isomer is used asan insecticide and in making dyes;the 1,4 compound is employed as adeodorant and moth repellent. | [Preparation]
1,4-Dichlorobenzene was first produced commercially in the United States in 1915 (IARC 1982). It is produced by reacting liquid benzene with gaseous chlorine in the presence of a catalyst at moderate temperature and atmospheric pressure. 1,4-Dichlorobenzene is used mainly as a fumigant for the control of moths, molds, and mildews, and as a space deodorant for toilets and refuse containers. | [Synthesis Reference(s)]
Chemistry Letters, 8, p. 939, 1979
The Journal of Organic Chemistry, 48, p. 250, 1983 DOI: 10.1021/jo00150a020
Tetrahedron Letters, 23, p. 371, 1982 DOI: 10.1016/S0040-4039(00)86833-1 | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Agricultural Uses]
Insecticide, Rodenticide, Fungicide: p-Dichlorbenzene is used primarily as an air deodorant,
as moth balls, and in insecticides, which accounts for
90% of the total production of this isomer. Information is
not available concerning the production and use of m-DCB.
However, it may occur as a contaminant of o-or p-DCB
formulations. Both o-and p-isomers are produced almost
entirely as byproducts during the production of monochlorobenzene.
The major uses of o-DCB are as a process solvent
in the manufacturing of toluene diisocyanate and as
an intermediate in the synthesis of dyestuffs, herbicides,
and degreasers. The para-isomer of dichlorobenzene is the
isomer most prominently used in agriculture. Not listed for
use in EU countries. | [Trade name]
DowTHERM®; EVOLA; PARACIDE®;
PARA CRYSTALS®; PARADI®; PARADOW®;
PARAMOTH®; PARANUGGETS®; PARAZENE®;
PERSIA-PERAZOL®; SANTOCHLOR®; Mixed isomers:
DILATIN DBI®; MOTTENSCHUTZMITTEL
EVAU P®; MOTT-EX®; TOTAMOTT® | [Carcinogenicity]
1,4-Dichlorobenzene is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. | [Environmental Fate]
Biological. In activated sludge, <0.1% degraded (mineralized) to carbon dioxide after 5 d
(Freitag et al., 1985). When 1,4-dichlorobenzene was statically incubated in the dark at 25 °C with
yeast extract and settled domestic wastewater inoculum, significant biodegradation with gradual
acclimation was followed by a deadaptive process in subsequent subcultures. At a concentration of
5 mg/L, 55, 61, 34, and 16% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively. At a concentration of 10 mg/L, only 37, 54, 29, and 0% losses were observed after 7,
14, 21, and 28-d incubation periods, respectively (Tabak et al., 1981).
Surface Water. Estimated half-lives of 1,4-dichlorobenzene (1.5 μg/L) from an experimental
marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 18,
10, and 13 d, respectively (Wakeham et al., 1983).
Groundwater. Nielsen et al. (1996) studied the degradation of 1,4-dichlorobenzene in a shallow,
glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm
study, a cylinder that was open at the bottom and screened at the top was installed through a cased
borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to
ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately
3 months to determine 1,4-dichlorobenzene concentrations with time. The experimentally
determined first-order biodegradation rate constant and corresponding half-life following a 22-d
lag phase were 0.05/d and 13.86 d, respectively.
Under anaerobic conditions, 1,4-dichlorobenzene in a plume of contaminated groundwater was
found to be very persistent (Barber, 1988).
Photolytic. Under artificial sunlight, river water containing 2 to 5 ppm of 1,4-dichlorobenzene
photodegraded to chlorophenol and phenol (Mansour et al., 1989). A carbon dioxide yield of 5.1%
was achieved when 1,4-dichlorobenzene adsorbed on silica gel was irradiated with light (λ >290
nm) for 17 h (Freitag et al., 1985). Irradiation of 1,4-dichlorophenol in air containing nitrogen
oxides gave 2,5-dichlorophenol (major product), 2,5-dichloronitrobenzene, 2,5-dichlorophenol,
and 2,5-dichloro-4-nitrophenol (Nojima and Kanno, 1980). The sunlight irradiation of 1,4-
dichlorobenzene (20 g) in a 100-mL borosilicate glass-stoppered Erlenmeyer flask for 56 d yielded
1,860 ppm 2′,4,5′-trichlorobiphenyl (Uyeta et al., 1976).
Chemical/Physical. Anticipated products from the reaction of 1,4-dichlorobenzene with ozone
or OH radicals in the atmosphere are chlorinated phenols, ring cleavage products, and nitro
compounds (Cupitt, 1980). | [Metabolic pathway]
1,4-Dichlorobenzene undergoes degradation by the
Xanthobacter flavus 14p1 isolated from river sludge by
selective enrichment with 1,4-dichlorobenzene,
resulting in the degradation products 3,6-dichloro-cis-
1,2-dihydroxycyclohexa-3,5-diene and 3,6-
dichlorocatechol. 2,5-Dichloromuconic acid and 2-
chloromaleylacetic acid, as well as the decarboxylation
product 2-chloroacetoacrylic acid, are identified after
enzymatic conversion of 3,6-dichlorocatechol. | [Purification Methods]
o-Dichlorobenzene is a common impurity. The p-isomer has been purified by steam distillation, crystallisation from EtOH or boiling MeOH, air-dried and dried in the dark under vacuum. It has also been purified by zone refining. [Beilstein 5 IV 658.] |
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