| Identification | More | [Name]
1,2-Dichlorobenzene | [CAS]
95-50-1 | [Synonyms]
1,2-DICHLOROBENZENE
AKOS BBS-00004357
DOWTHERM(R) E
O-DICHLOROBENZENE
ORTHODICHLOROBENZENE
1,2-Dichlorbenzene
1,2-Dichlorbenzol
1,2-dichloro-benzen
2-dichlorobenzene
ai3-00053
Benzene, o-dichloro-
Benzene,1,2-dichloro-
Benzene,o-dichloro-
caswellno301
Chloroben
Chloroden
Cloroben
Dichlorobenzene, o-
Dichlorobenzene, ortho
dichlorobenzene,ortho,liquid | [EINECS(EC#)]
202-425-9 | [Molecular Formula]
C6H4Cl2 | [MDL Number]
MFCD00000535 | [Molecular Weight]
147 | [MOL File]
95-50-1.mol |
| Chemical Properties | Back Directory | [Appearance]
There are three isomeric forms of dichlorobenzene (DCB):
m-DCB is a flammable liquid and vapor. | [Melting point ]
-15 °C | [Boiling point ]
179 °C | [density ]
1.306 g/mL at 25 °C(lit.)
| [vapor density ]
5.1 (vs air)
| [vapor pressure ]
1.2 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.551
| [Fp ]
150 °F
| [storage temp. ]
0-6°C | [solubility ]
0.13g/l | [form ]
Liquid | [color ]
Clear colorless to very slightly yellow | [Odor]
Aromatic; characteristic aromatic. | [Stability:]
Stable, but possibly light sensitive. Combustible. Incompatible with oxidizing agents, aluminium, aluminium alloys. Attacks some rubbers and plastics. | [explosive limit]
2.2-12%(V) | [Water Solubility ]
0.13 g/L (20 ºC) | [λmax]
λ: 296 nm Amax: 1.00
λ: 300 nm Amax: 0.30
λ: 305 nm Amax: 0.20
λ: 335 nm Amax: 0.05
λ: 375-400 nm Amax: 0.01 | [Merck ]
14,3056 | [BRN ]
606078 | [Henry's Law Constant]
1.92 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997) | [Dielectric constant]
7.5（20℃） | [Exposure limits]
Ceiling 50 ppm (～300 mg/m3) (MSHA,
OSHA, and NIOSH); IDLH 1700 ppm
(NIOSH). | [LogP]
3.433 at 25℃ | [CAS DataBase Reference]
95-50-1(CAS DataBase Reference) | [IARC]
3 (Vol. Sup 7, 73) 1999 | [NIST Chemistry Reference]
Benzene, 1,2-dichloro-(95-50-1) | [EPA Substance Registry System]
95-50-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,Xi,F,T | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R67:Vapors may cause drowsiness and dizziness.
R66:Repeated exposure may cause skin dryness or cracking.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36:Irritating to the eyes.
R11:Highly Flammable.
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 .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
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 .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [RTECS ]
CZ4500000
| [Autoignition Temperature]
640 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29036100 | [Safety Profile]
Poison by ingestion and
intravenous routes. Moderately toxic by
inhalation and intraperitoneal routes. An
experimental teratogen. Other experimental
reproductive effects. An eye, skin, and
mucous membrane irritant. Causes liver and
hdney injury. Questionable carcinogen.
Mutation data reported. A pesticide.
Flammable when exposed to heat or flame.
Can react vigorously with oxidizing
materials. To fight fire, use water, foam,
CO2, or dry chemical. Slow reaction with
aluminum may lead to explosion during
storage in a sealed aluminum container. When heated to decomposition it emits
toxic fumes of Cl-. See also
CHLOROBENZENE and
CHLORINATED HYDROCARBONS,
AROMATIC. | [Hazardous Substances Data]
95-50-1(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 500 mg/kg LD50 dermal Rabbit > 10000 mg/kg | [IDLA]
200 ppm |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Benzene-->Chlorine-->Copper(I) chloride-->2-Chloroaniline | [Preparation Products]
3,5-Dichloroaniline-->Norfloxacin-->METHYLISOCYANATE 1 X 500MG NEAT-->Coumarin 6-->Pigment Geen 7-->Butyl isocyanate-->3,4-Dichloroaniline-->3-Amino-5-methylisoxazole-->Mebendazole-->VAT BLACK 27-->3-Chloro-4-fluoroaniline-->Permanent Violet RL-->1,4-Dichlorobenzene-->DIRECT YELLOW 27-->2,6-Dichlorobenzonitrile-->3,4-Dichloronitrobenzene-->1,2,4,5-TETRACYANOBENZENE-->Acenaphthenequinone-->1,3-Dichloroisoquinoline-->4-(3-METHYL-UREIDO)-BENZENESULFONYL CHLORIDE-->1,2,4,5-BENZENETETRACARBOXAMIDE-->1-Naphthyl isocyanate-->N,N,N',N'-Tetraphenylbenzidine-->2,7-DIBROMO-9H-CARBAZOLE-->2,4,6-Trimethoxybenzaldehyde-->PYROMELLITIC DIIMIDE-->3，7-dichloro-8-dichloro methyl quinoline-->3，7-dichloro-8-chloro methyl quinoline-->2-NAPHTHYL ISOCYANATE-->4,5-Dichloro-1,2-benzenediamine-->3,4-Dichlorobenzophenone-->3,5-Dibromo-4-hydroxybenzaldehyde-->Pigment Red 176-->(3,4-Diaminophenyl)phenylmethanone-->tert-Butylisocyanate-->Acetofenate-->C. I. Pigment Yellow 173-->3,4-Dichlorobenzaldehyde-->DICHLORPHENAMIDE-->4,5-DICHLORO-BENZENE-1,3-DISULFONYLDICHLORIDE |
| Hazard Information | Back Directory | [General Description]
A clear colorless liquid with a pleasant odor. Denser than water and insoluble in water. Flash point 150°F. Toxic by inhalation and ingestion. Used to make other chemicals, solvents, fumigants and insecticides and for many other uses. | [Reactivity Profile]
O-DICHLOROBENZENE(95-50-1) is sensitive to prolonged exposure to light. This chemical can react vigorously with oxidizers. O-DICHLOROBENZENE(95-50-1) is incompatible with aluminum and aluminum alloys. O-DICHLOROBENZENE(95-50-1) attacks some forms of plastics, rubber and coatings. . | [Air & Water Reactions]
Insoluble in water. | [Health Hazard]
Chronic inhalation of mist or vapors may result in damage to lungs, liver, and kidneys. Acute vapor exposure can cause symptoms ranging from coughing to central nervous system depression and transient anesthesia. Irritating to skin, eyes, and mucous membranes. May cause dermatitis. | [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: Poisonous vapors including hydrogen chloride gas, chlorocarbons, chlorine | [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. | [Chemical Properties]
1,2-Dichlorobenzene (DCB, o-Dichlorobenzene, ODB, Orthodichlorobenzene),
C6H4Cl2, is a colorless to pale yellow liquid with a pleasant aromatic odor. It is a
combustible liquid and can form explosive mixtures with air at or above 151°F.
Combustion and thermal decomposition products include hydrogen chloride gas,
phosgene and chloro-carbons. Its flammable (explosive) limits are as follows:
Lower 2.2%, Upper 9.2%.
| [Chemical Properties]
colourless liquid | [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]
Clear, colorless to pale yellow liquid with a pleasant, aromatic, grassy or vegetable-type odor. At
40 °C, the lowest concentration at which an odor was detected was 200 μg/L. At 25 °C, the lowest
concentration at which a taste was detected was 200 μg/L (Young et al., 1996). A detection odor
threshold concentration of 4.2 mg/m3 (699 ppbv) was reported by Punter (1983). | [Uses]
1,2-Dichlorobenzene is used as a solvent; asa fumigant; as an insecticide for termites;as a degreasing agent for metals, wool, andleather; and as a heat transfer medium. | [Uses]
Organic synthesis (primarily 3,4-
dichloroaniline); solvent; insecticide; dye
manufacture | [Uses]
Solvent for waxes, gums, resins, tars, rubbers, oils, asphalts; insecticide for termites and locust borers; fumigant; deodorizer; removing sulfur from illuminating gas; as degreasing agent for metals, leather, wool; as ingredient of metal polishes; as heat transfer medium; as intermediate in the manufacture of dyes. | [Definition]
ChEBI: A dichlorobenzene carrying chloro substituents at positions 1 and 2. | [Production Methods]
Dichlorobenzenes are primarily produced by the chlorination of benzene in the presence of a catalyst (FeCl3 or AlCl3) although there are other possible synthetic routes. The two commercially important isomers are the ortho- and para-dichlorobenzenes. | [Flammability and Explosibility]
Nonflammable | [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. | [Environmental Fate]
Biological. Pseudomonas sp. isolated from sewage samples produced 3,4-dichloro-cis-1,2-
dihydroxycyclohexa-3,5-diene. Subsequent degradation of this metabolite yielded 3,4-
dichlorocatechol, which underwent ring cleavage to form 2,3-dichloro-cis,cis-muconate, followed
by hydrolysis to form 5-chloromaleylacetic acid (Haigler et al., 1988). When 1,2-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, 45, 66, 48, and 29% losses were
observed after 7, 14, 21, and 28-d incubation periods, respectively. At a concentration of 10 mg/L,
only 20, 59, 32, and 18% losses were observed after 7, 14, 21, and 28-d incubation periods,
respectively (Tabak et al., 1981).
Groundwater. Nielsen et al. (1996) studied the degradation of 1,2-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 1,2-dichlorobenzene concentrations with time. The experimentally
determined first-order biodegradation rate constant and corresponding half-life following a 13-d
lag phase were 0.06/d and 11.55 d, respectively.
Photolytic. Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ
= 365 nm) converted 1,2-dichlorobenzene to carbon dioxide at a significant rate (Matthews, 1986).
The sunlight irradiation of 1,2-dichlorobenzene (20 g) in a 100-mL borosilicate glass-stoppered
Erlenmeyer flask for 56 d yielded 2,270 ppm 2,3′,4′-trichlorobiphenyl (Uyeta et al., 1976).
When an aqueous solution containing 1,2-dichlorobenzene (190 μM) and a nonionic surfactant
micelle (Brij 58, a polyoxyethylene cetyl ether) was illuminated by a photoreactor equipped with
253.7-nm monochromatic UV lamps, photoisomerization took place yielding 1,3- and 1,4-
dichlorobenzene as the principal products. The half-life for this reaction, based on the first-order
photodecomposition rate of 1.35 x 10-3/sec, is 8.6 min (Chu and Jafvert, 1994).
Chemical/Physical. Anticipated products from the reaction of 1,2-dichlorobenzene with ozone
or OH radicals in the atmosphere are chlorinated phenols, ring cleavage products, and nitro
compounds (Cupitt, 1980). Based on an assumed base-mediated 1% disappearance after 16 d at 85
°C and pH 9.70 (pH 11.26 at 25 °C), the hydrolysis half-life was estimated to be >900 yr
(Ellington et al., 1988). | [storage]
Color Code—Red (o-DCB): Flammability Hazard:Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactivematerials.
Color Code—Blue (m-DCB): Health Hazard/Poison: Storein a secure poison location.
Color Code—Green (p-DCB): General storage may be used.Prior to working with any DCB you should be trained on itsproper handling and storage. Before entering confined space where this chemical may be present, check to make surethat an explosive concentration does not exist.Dichlorobenzene must be stored to avoid contact withstrong oxidizers, such as permanganates, nitrates, peroxides,chlorates, and perchlorates, hot aluminum or aluminumalloys since violent reactions occur. Store in tightly closedcontainers in a cool, well-ventilated area away from heatand direct light. Sources of ignition, such as smoking andopen flames, are prohibited where dichlorobenzene is used,handled, or stored in a manner that could create a potentialfire or explosion hazard. A regulated, marked area shouldbe established where p-DCB is handled, used, or stored incompliance with OSHA Standard 1910.1045. | [Purification Methods]
Contaminants may include the p-isomer and trichlorobenzene [Suslick et al. J Am Chem Soc 106 4522 1984]. It should be shaken with conc or fuming H2SO4, washed with water, dried with CaCl2, and distilled from CaH2 or sodium in a glass-packed column. Low conductivity material (ca 10-10 mhos) has been obtained by refluxing with P2O5, fractionally distilling and passing it through a column packed with silica gel or activated alumina: it is stored in a dry-box under N2 or with activated alumina. [Beilstein 5 IV 654.] |
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