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Home > Encyclopedia > 1,4-Dibromobenzene

1,4-Dibromobenzene

1,4-Dibromobenzene structure

1,4-Dibromobenzene 

structure
  • CAS No:

    106-37-6

  • Formula:

    C6H4Br2

  • Chemical Name:

    1,4-Dibromobenzene

  • Synonyms:

    Benzene,1,4-dibromo-;Benzene,p-dibromo-;1,4-Dibromobenzene;p-Dibromobenzene;p-Bromophenyl bromide;para-Dibromobenzene;p-Phenylene dibromide;NSC 33942

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

white or off-white powder Dibromobenzene is a heavy colorless liquid. Pleasant aromatic odor.


1,4-dibromobenzene is a dibromobenzene.

1,4-Dibromobenzene Basic Attributes

235.9

235.90

1904543

203-390-2

9991W3M5HZ

33942

DTXSID4024012

PLATES|COLORLESS CRYSTALS

29036990

Characteristics

0

3.8

Colorless to almost white Crystals

0.9641 g/cm3 @ Temp: 99.6 °C

87.3 °C

220.40 °C

219-220°C

1.5742

Practically insoluble in water;soluble in alcohol, benzene, chloroform, toluene and carbon tetrachloride. Insoluble in ether.

Store below +30°C.

0.134 at 35 °C (Hine et al., 1963)

8.1 (Air= 1)

Oral-Mouse LD50: 3120 mg/kg; Abdominal cavity-mouse LD50: 1891 mg/kg

Thermal decomposition releases toxic bromide vapor

ODOR OF XYLENE

Dielectric constant: 7.77 at 10 °C; 6.7 at 40 °C; dipole moment: 1.43 (gas), 1.85 in liquid at 20 °C|Heat of fusion: 20.55 cal/g= 85.98 J/g= 20,284 J/mol|UV: 5-46 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York) /o-Dibromobenzene/

13,047.8 g cal/g mole

Safety Information

III

9

UN 2711

2

36/37/38

24/25-36-26

CZ1791000

Xi

Warehouse ventilated, low temperature and dry

Stable. Combustible. Incompatible with strong oxidizing agents.

P261-P273-P305 + P351 + P338

H315-H319-H335-H400

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H315 (98.46%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 65 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]|P260, P264, P270, P273, P314, P391, and P501

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus. /Dibromobenzene/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Dibromobenzene/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. /Dibromobenzene/|Personnel protection: Keep upwind. Avoid breathing vapors. ... /Dibromobenzene/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Dibromobenzene/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Dibromobenzene/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Dibromobenzene/|/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dibromobenzene/|For more DOT Emergency Guidelines (Complete) data for P-DIBROMOBENZENE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

moderately toxic

The halogenated benzenes, inducers of xenobiotic metabolism, were studied for their effects on the metabolism of malathion, malaoxon (lindane), and paraoxon and on the toxicity and lethality of these organophosphorus insecticides and parathion. One mmol/kg of 1,4-dichlorobenzene (p-dichlorobenzene), 1,2,4-trichlorobenzene, 1,4-dibromobenzene, 1,2,4-tribromobenzene, or hexabromobenzene or 0.1 mmol/kg hexachlorobenzene was administered po to male mice daily for 7 days. In general, the trihalogenated benzenes increased the LD50 of all 4 insecticides 2- to 6-fold. These increases were larger than those observed with the di- or hexahalogenated isomers. The bromide-substituted benzenes were usually more active than the chlorinated ones with the exception being hexabromobenzene. There was a good correlation between their effects on lethality and increases in in vitro carboxylesterase activity with either-malathion or malaoxon as the substrate. The trihalogenated benzenes decreased the inhibitory effect of malathion on cholinesterase activity in the brain and to a lesser degree in the red blood cells, but not in 1iver or plasma.

p-Dibromobenzene's production and use in the organic synthesis of dyestuffs and drugs, the manufacture of intermediates and as a fumigant(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2,700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that p-dibromobenzene will have slight mobility in soil(SRC). Volatilization of p-dibromobenzene will be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 8.93X10-4 atm-cu m/mole(SRC), calculated using experimental vapor pressure(4) and water solubility(5). Volatilization from dry soil surfaces(SRC) should not be important based on an experimental vapor pressure of 0.0575 mm Hg(4,SRC). Based on limited screening data, p-dibromobenzene is resistant to biodegradation; after a period of two weeks, 0% biodegradation occurred(6).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 2700(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(1), indicates that p-dibromobenzene may adsorb to suspended solids and sediment in water(SRC). p-Dibromobenzene will volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 8.33X10-4 atm-cu m/mole(SRC), calculated using experimental vapor pressure(3) and water solubility(4). Estimated half-lives for a model river and model lake are 6 and 157 hrs, respectively(1,SRC). According to a classification scheme(5), experimental BCF values ranging from 42.9 to 1,413(6,7,SRC) suggests that bioconcentration in aquatic organisms is moderate to very high(SRC). Based on limited screening data, this compound is resistant to biodegradation; 0 biodegradation occurred after a period of two weeks(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-dibromobenzene, which has an experimental vapor pressure of 0.0575 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Vapor-phase p-dibromobenzene is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 46 days(3,SRC). Particulate-phase p-dibromobenzene may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of p-dibromobenzene with photochemically produced hydroxyl radicals has been estimated as 0.35X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 46 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

162.18|An experimental BCF value of 1,413 was determined for p-dibromobenzene(2,SRC) in the guppy (Poecilia reticulata). Studies also showed a depuration rate constant of 1.41 /d(2). When exposed to 10 ug/l p-dibromobenzene, the experimental BCF in carp ranged from 42.9 to 313. When exposed to 1 ug/l p-dibromobenzene, the experimental BCF ranged from 44.2 to 279(1). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms is moderate to very high(SRC).

The Koc of p-dibromobenzene is estimated as approximately 2,700(SRC), using an experimental log Kow of 3.79(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that p-dibromobenzene has slight mobility in soil(SRC).

The Henry's Law constant for p-dibromobenzene is estimated as 8.93X10-4 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 0.0575 mm Hg(1), and water solubility, 20.0 mg/l(2). This value indicates that p-dibromobenzene will volatilize from water surfaces(3,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 5.9 hours(3,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 157 days(3,SRC). p-Dibromobenzene's values for vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil surfaces may occur(SRC).

Probable routes of exposure to p-dibromobenzene are inhalation and dermal contact. (SRC)

Drug Information

FOLLOWING IP ADMIN OF P-DIBROMOBENZENE TO RABBITS, BOTH 2,4- & 2,5-DIBROMO PHENOL WERE RECOVERED IN THE URINE SUGGESTING THE FORMATION OF AN ARENE OXIDE AS AN INTERMEDIARY METABOLITE.|FOLLOWING IP ADMIN OF P-DIBROMOBENZENE TO PIGS, BOTH 2,4- & 2,5-DIBROMOPHENOL WERE RECOVERED IN THE URINE SUGGESTING THE FORMATION OF AN ARENE OXIDE AS AN INTERMEDIARY METABOLITE.

2.04 Days

1,4-dibromobenzene

1,4-Dibromobenzene Use and Manufacturing

Methods of Manufacturing

Derived from benzene bromide.

Uses

Solvent for oils; ore flotation; motor fuels; organic synthesis.

Benzene, 1,4-dibromo-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Negative ion chemical ionization mass spectrometry is evaluated as a method for qualitative and quantitative determination of polyhalogenated aromatic hydrocarbons, including p-dibromobenzene. Each cmpd or mixture of cmpd is analyzed by glass capillary gas chromatography-mass spectrometry by using different modes of chemical ionization in the mass spectrometer.

Computed Properties

Molecular Weight:235.90
XLogP3:3.8
Exact Mass:235.86593
Monoisotopic Mass:233.86798
Heavy Atom Count:8
Complexity:54.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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