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Bromobenzene

Bromobenzene structure

Bromobenzene 

structure
  • CAS No:

    108-86-1

  • Formula:

    C6H5Br

  • Chemical Name:

    Bromobenzene

  • Synonyms:

    Benzene,bromo-;Bromobenzene;Monobromobenzene;Phenyl bromide;NSC 6529;1-Bromobenzene;Bromobenzol

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

colourless liquidMobile clear colorless liquid with a pungent odor. Flash point 124°F. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. A skin irritant.Mobile, clear, colorless to pale yellow liquid with an aromatic odor. The reported odor threshold is 4.6 ppm (Mateson, 1955).


Mobile clear colorless liquid with a pungent odor. Flash point 124°F. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. A skin irritant.|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.


Mobile clear colorless liquid with a pungent odor. Flash point 124°F. Denser than water and insoluble in water. Hence sinks in water. Vapors are heavier than air. A skin irritant.|Bromobenzene is the simplest member of the class of bromobenzenes, that is benzene in which a single hydrogen has been substituted by a bromine. A liquid at room temperature (m.p. -30℃; b.p.760 156℃), it is used as a solvent, particularly for large-scale crystallisations, and for the introduction of phenyl groups in organic synthesis. It has a role as a non-polar solvent, a hepatotoxic agent and a mouse metabolite. It is a member of bromobenzenes, a bromoarene and a volatile organic compound.

Bromobenzene Basic Attributes

157.01

157.01

1236661

203-623-8

CO4D5J547L

1016

6529

2514

DTXSID5024637

MOBILE LIQUID|Heavy, mobile, colorless liquid

2903 99 80

Characteristics

0

2.99

Clear colorless to faintly yellow Liquid

1.5 g/cm3

-30.7 °C

156.2 °C @ Press: 760 Torr

124 °F

n 20/D 1.559(lit.)

H2O: insoluble . <0.1 g/100 mL at 20.5 ºC.Miscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.

2-8°C

10 mm Hg ( 40 °C)

5.41 (vs air)

Oral-Rat LD50: 2699 mg/kg; Oral-Mouse LD50: 2700 mg/kg

Combustible in case of open flame, high temperature and strong oxidant; burning produces toxic bromide fumes

0.5-2.5%(V)

AROMATIC ODOR

7.70e-13 cm3/molecule*sec

0.00 atm-m3/mole

HEAT OF MELTING 16.186 CAL/G @ 15 °C; SPECIFIC HEAT @ 26.84 °C: 0.2368|WT/GAL 12.51 LB|LIQUID-WATER INTERFACIAL TENSION: (EST) 30 DYNES/CM= 0.030 NEWTONS/M @ 20 °C|Heat of Fusion = 10.62 kJ/mol @ 25 °C|For more Other Experimental Properties (Complete) data for BROMOBENZENE (7 total), please visit the HSDB record page.

Flammable. Insoluble in water.

Aryl Halides

BROMOBENZENE may be sensitive to light. May react with oxidizing agents (NTP, 1992).

1049 °F (USCG, 1999)|1049 °F (565 °C)|566 °C

-8,510 BTU/LB= -4,730 CAL/G= -198X10+5 JOULES/KG

As a result of flow, agitation, etc., electrostatic charges can be generated.

44.5 kJ/mol @ 25 °C

CRITICAL TEMP 397 °C; CRITICAL PRESSURE 33,912 MM HG (44.6 ATM)

Safety Information

III

3

UN 2514 3/PG 3

2

10-38-51/53-39/23/24/25-23/24/25

61-45-36/37

CY9000000

Xi,N,F,T

Completely packed, lightly placed; storeroom ventilated, away from open flames, high temperature, and stored separately from oxidants

Explosive when mixed with air

Stable. Combustible. Incompatible with strong oxidizing agents.

P273

H226-H315-H411

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.

DANGEROUS...CAN REACT WITH OXIDIZING MATERIALS.

Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire. (USCG, 1999)|Flammable. Above 51 °C explosive vapour/air mixtures may be formed.|Flammable - 2nd degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+P352, P303+P361+P353, P321, P332+P313, P362, P370+P378, P391, P403+P235, and P501|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|Aggregated GHS information provided by 108 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P302+P352, P303+P361+P353, P304+P340, P311, P314, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Goggles or face shield; rubber gloves and apron. (USCG, 1999)|GOGGLES OR FACE SHIELD; RUBBER GLOVES & APRON.

MODERATE, WHEN EXPOSED TO HEAT OR FLAME...

Explosive limits , vol% in air: 6-36.5

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. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical or carbon dioxide.

A MIXT OF PIPERIDINE, CYCLOHEXANONE, AND BROMOBENZENE WAS BURNED IN A HOUSE TO SIMULATE A FIRE IN A PHENCYCLIDINE LAB. BROMOBENZENE WAS DETECTED IN/ON THE DEBRIS HEADSPACE, SHOES WORN DURING THE INCIDENT, AND LIQ DISTILLATE FROM THE DEBRIS. IT WAS ALSO DETECTED IN A VACUUM GRAB SAMPLE AND ON VAPORS TRAPPED ON A CHARCOAL TUBE.

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. Use water spray to knock-down vapors.|Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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 or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (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.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/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.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for BROMOBENZENE (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 Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|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.

IRRITANT TO SKIN.

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible.

Fireproof. Ventilation along the floor.

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

The substance is irritating to the skin. If this liquid is swallowed, aspiration into the lungs may result in chemical pneumonitis. The substance may cause effects on the nervous system.

The substance may have effects on the liver and kidneys. This may result in impaired functions.

NO open flames. NO open flames, NO sparks and NO smoking. Above 51 °C use a closed system, ventilation and explosion-proof electrical equipment. Prevent build-up of electrostatic charges (e.g., by grounding).

PREVENT GENERATION OF MISTS!

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

ORGANIC CONSTITUENTS OF SECONDARY EFFLUENTS FROM PUBLICLY-OWNED TREATMENT WORKS IN ILLINOIS WERE ANALYZED BY CAPILLARY GAS CHROMATOGRAPHY-MASS SPECTROSCOPY. EMPHASIS WAS GIVEN TO SECONDARY EFFLUENTS FROM MUNICIPAL TREATMENT PLANTS RECEIVING INDUSTRIAL DISCHARGES AS PART OF THE INFLUENT. BROMOBENZENE WAS DETECTED IN ONE COMPOSITE SAMPLE FROM THE FIRST MANHOLE DOWNSTREAM OF A TREATMENT PROCESS.|Sample extracts from four different incineration site effluents, location unknown; bromobenzene was found to have a concn of 2.8 ug/l at site II and a concn of 99 ug/l at site III. No detection was found at the other sites(1). Fly ash from a municipal waste incinerator, location unknown, was substituted by bromide without changing the catalytic properties of the fly ash. At three different bromide concns of 10, 20, and 30 wt%, bromobenzene was formed on the fly ash in concns of 2319, 6099, and 9752 ng/g, respectively(2). Bromobenzene was confirmed as being present in chlorinated secondarily-treated effluent from the Mililani Sewage Treatment Plant in unreported concns(3). Bromobenzene was effectively removed by percolation through Lahaina soil (23 cm deep) when treated effluent was applied as irrigaton water to a sugarcane field(3).

In 1979, environmental samples (number unknown) were collected off site of bromine industry plants near El Dorado and Magnolia, Arkansas. Unreported concentrations of bromobenzene were identified in the soil and sediment(1).

SOURCE DOMINATE: Ambient air concns of bromobenzene were collected over a five day period (7/17/77 to 7/21/77) near Great Lakes Chemical Corp in El Dorodo, Arkansas. Twenty-one samples from five different locations were collected. Results showed that the levels of bromobenzene ranged from 5.3 ng/l (period 1, cycle 1, location 1) to 4,276 ng/l (period 3, cycle 1, location 3)(1). Ambient air concns of bromobenzene were collected over a two year period (1976 to 1977) near Great Lakes Chemical Corp in El Dorado, Arkansas and a one day period in 1977 in Magnolia, Arkansas. Concns in El Dorodo ranged from 4.8 ng/cu m to 4,276 ng/cu m. Concns in Magnolia ranged from 23 ng/cu m to 140 ng/cu m(2).|URBAN/SUBURBAN: In an update of the Volatile Organic Compounds Database, bromobenzene was found to have an average daily concentration of 0.224 ppbv for all ambient site types (indoor/outdoor). This was determined from 26 data points(1).

Toxicity

moderately toxic

...BROMOBENZENE...CENTRILOBULAR NECROSIS. ...COULD BE PREVENTED BY COADMINISTRATION OF CYSTEINE & METHIONINE... PIPERONYL BUTOXIDE /ALSO/ PREVENTED LIVER NECROSIS...|IN ISOLATED RAT HEPATOCYTES, METHIONINE PREVENTED BROMOBENZENE TOXICITY, PRESUMABLY BY STIMULATING GSH SYNTHESIS & THEREBY DECR AMT OF REACTIVE METABOLITES AVAILABLE. HEPATOCYTES FROM DIETHYLMALEATE-TREATED RATS WERE SENSITIVE TO BROMOBENZENE TOXICITY UNDER INCUBATION CONDITIONS.|PRIOR CONSUMPTION OF A DIET CONTAINING BUTYLATED HYDROXYANISOLE BY FEMALE MICE PREVENTED THE DEVELOPMENT OF OR MINIMIZED THE ACUTE LIVER DAMAGE CAUSED BY BROMOBENZENE.|CHOLESTYRAMINE-FED RATS AND PAIR-FED CONTROLS WERE ADMIN BROMOBENZENE IP FIVE DAYS LATER. CHOLESTYRAMINE PREVENTED LIVER NECROSIS.|For more Interactions (Complete) data for BROMOBENZENE (8 total), please visit the HSDB record page.

Bromobenzene's production and use as an additive to motor oil, in organic synthesis to make phenyl magnesium bromide, as a solvent for crystallization on a large scale, and where a heavy liquid is desirable(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 268(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(3), indicates that bromobenzene will have moderate mobility in soil(SRC). Volatilization of bromobenzene may be important from moist soil surfaces(SRC) given an experimental Henry's Law constant of 2.08X-3 atm-cu m/mole(4,SRC). Based on limited screening test data, bromobenzene is resistant to biodegradation; after a period of four weeks, 0% biodegradation occurred(5).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 268(SRC), determined from an experimental log Kow(2,SRC) and a recommended regression-derived equation(1), indicates that bromobenzene may adsorb to suspended solids and sediment in water(SRC). Bromobenzene will volatilize from water surfaces(1,SRC) based on an experimental Henry's Law constant of 2.08X10-3 atm-cu m/mole(3,SRC). Estimated half-lives for a model river and model lake are 4 hours and 5 days, respectively(1,SRC). According to a classification scheme(4), experimental BCF values in the range of 8.8 to 190(5,6,SRC) suggests that bioconcentration in aquatic organisms is low to moderately high(SRC). Based on limited screening test data, bromobenzene is moderately resistant to biodegradation; after a period of four weeks, 0% biodegradation occurred(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromobenzene, which has an experimental vapor pressure of 4.18 mm Hg at 25 °C(2,SRC), will exist solely as a vapor in the ambient atmosphere. Vapor-phase bromobenzene 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 21 days(SRC) from the experimentally measured hydroxyl radical rate constant of 7.7X10-13 at 25 °C(3). Particulate-phase bromobenzene may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of bromobenzene with photochemically produced hydroxyl radicals has been experimentally determined as 7.7X10-13 cu cm/molecule-sec at 25 °C utilizing the flash photolysis resonance fluorescence technique(1). This corresponds to an atmospheric half-life of about 21 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(SRC). In another study, bromobenzene was absorbed on silica gel and irradiated with light at a wavelength of 290 nm. Irradiation produced 19.7 percent photooxidation of bromobenzene(2).

22.91|When exposed to 50 ug/l of bromobenzene, the experimental BCF in carp ranged from 8.8 to 34. When exposed to 5 ug/l of bromobenzene, the experimental BCF in carp ranged from 12 to 33(1). The experimental BCF in algae (Chlorella fusca) was 190 for one day. The experimental BCF for the fish golden ide (Leuciscus idus melanotus) was determined to be 50 after three days(2). Concentration of bromobenzene in the water for the algae and the golden ide was unreported(2). According to a classification scheme(3), these BCF values suggest that bioconcentration in aquatic organisms ranges from low to moderately high(SRC).

309.03 L/kg|The Koc of bromobenzene is estimated as approximately 268 (SRC), using an experimental log Kow of 2.99 (1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that bromobenzene has moderate mobility in soil(SRC).

The Henry's Law constant for bromobenzene has been experimentally determined as 2.08X10-3 atm-cu m/mole(1,SRC). This value indicates that bromobenzene will volatilize from water surfaces(2,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 4 hours(2,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 5 days(2,SRC).

DURING CHLORINATION WATER TREATMENT, BROMOBENZENE CAN BE FORMED IN SMALL QUANTITIES.../HAS BEEN/ FOUND IN FINISHED WATER IN LOWER MISSISSIPPI RIVER AREA...|GROUNDWATER: In a study conducted by the Office of Technology Assessment in 1984, bromobenzene was known to occur in groundwater ranging in concn from 1.9 ppb to 5.8 ppb(1). Disposal of secondary sewage effluent by rapid infiltration since 1936 has produced a plume of contaminated groundwater over 3500 m long near Falmouth, MA. Bromobenzene was identified as a contaminant with a maximum concn of 10 ng/l(2). Bromobenzene was found to be a contaminant in groundwater from a well near a chemical plant in Switzerland. Results showed that a maximum of 16 ug/l bromobenzene was present in well number one, which was closest to the chemical plant(3). Screening of 1174 community wells and 617 private wells was conducted in Wisconsin in the early 1980's. GCMS results showed that bromobenzene was detected in the wells, in unreported concns(4). Random samples of finished water were collected near a point of entrance to the distribution system from the public water systems in Ohio during 1981 and 1982. A total of 479 samples was taken statewide. Bromobenzene was detected three times from a random selection of 280 sites serving fewer that 10,000 persons at an average concn of 0.5 ug/l. Bromobenzene was detected one time from a random selection of 186 sites serving more than 10,000 persons at an average concn of 0.5 ug/l(5).|GROUNDWATER: Results of the 1982 Ground Water Supply Survey showed that in a random sampling of 466 wells, bromobenzene was found to have an average concn of 0.5 ug/l in drinking water(1).|SURFACE WATER: Thirty samples were collected between February 17 and February 20, 1976 in the Delaware Basin along the Delaware, Schuylkill and Lehigh rivers between Allentown,PA and Margaretville,DE. The samples were taken from the navigational channel in the middle of the river. Exact concns of bromobenzene were not determined, but bromobenzene was detected as occurring at a frequency of seven percent(1). A total of 204 water samples were collected from fourteen heavily industrialized river basins across the United States between the 18-month period of July 1, 1975 and December 31, 1976. Exact concns of bromobenzene were not determined, but bromobenzene was detected as occurring at a frequency of nine percent(2).

Using EPA Method 524.2, bromobenzene was detected in two of 234 table foods(1). The concentration ranged from 4.69 ppb to 9.06 ppb. The highest level food item was cake doughnuts.

Probable routes of exposure to bromobenzene from occupational situations are inhalation and dermal contact from it's production and use as well as consumer exposure to motor oil. Due to the compound's presence in food, ambient air, and finished water, general population exposure may be possible by ingestion and inhaltion routes. (SRC)

The concentration of total bromobenzenes in human adipose tissue for three specimens from Japan was 2.1, 2.9, and 4.1 ng/wet,g(1).

Drug Information

4 (?). 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB).

ABSORBED THROUGH LUNGS, GI TRACT & INTACT SKIN. EXCRETED AS CATECHOL DERIVATIVES BOTH FREE & CONJUGATED WITH SULFATE OR MERCAPTURIC ACID.|BROMOBENZENE MAY BE METAB TO AN EPOXIDE...EXCRETED IN BILE, REABSORBED THROUGH ENTEROHEPATIC CIRCULATION, & METAB IN SEVERAL STEPS TO S-(P-BROMOPHENYL)MERCAPTURIC ACID, WHICH IS THEN EXCRETED IN URINE.|This investigation was designed to determine whether biliary excretion of bromobenzene-glutathione conjugate can be used as an index of in vivo activation of bromobenzene. To test this hypothesis, the effect of chemicals known to alter the toxicity and biotransformation of bromobenzene (ie, cytochrome p450 inducers and inhibitors) on the biliary excretion of bromobenzene-glutathione was studied in rats. Bromobenzene-glutathione was the major bromobenzene metabolite in bile. A linear relationship was observed between the dosage of bromobenzene administered and bromobenzene-glutathione excreted into bile, up to a dosage of 250 umol/kg of bromobenzene. Of the inducers tested, Phenobarbital, which is known to increase the toxicity of bromobenzene, dramatically increased 1700 m1 the rate of biliary excretion of bromobenzene-glutathione over that in control animals. In contrast, 3-methylcholanthrene, which is known to decrease the hepatotoxicity of bromobenzene, decreased the biliary excretion of bromobenzene-glutathione (56%). Inhibitors of p450, such as SKF 525-A and piperonyl butoxide which are known to decrease the activation and hepatotoxicity of bromobenzene, also decreased the biliary excretion of bromobenzene-glutathione. These findings are in agreement with the hypothesis that the biliary excretion of bromobenzene-glutathione reflects the formation of the reactive bromobenzene metabolite in liver and the rate of biliary excretion can be used to determine factors that are important in determining the toxicity of bromobenzene.

IT APPEARS THAT IN BROMOBENZENE NECROSIS /OF LIVER/, THE TOXIC /SRP: BROMOBENZENE EPOXIDE METABOLITES, MAINLY THE 3,4-EPOXIDE, ARE/...DEGRADED THROUGH THE ACTION OF GLUTATHIONE TRANSFERASE & EPOXIDE HYDRATASE.|BROMOBENZENE IS METABOLIZED VIA THE HEPATIC MIXED-FUNCTION OXIDASE SYSTEM TO REACTIVE INTERMEDIATES 2,3- AND 3,4-BROMOBENZENE EPOXIDES. THESE METABOLITES PRESUMABLY BIND TO TISSUE MACROMOLECULES. THE SPECIFIC SITES OF MACROMOLECULAR PROTEINS WERE INVESTIGATED. THE 3,4-EPOXIDE IS MORE REACTIVE, BINDING COVALENTLY TO MICROSOMAL PROTEIN AT THE SITE OF ITS SYNTHESIS, WHEREAS BROMOBENZENE 2,3-EPOXIDE IS MORE STABLE, LEAVING THE MICROSOMAL PROTEIN COMPARTMENT AND BINDING COVALENTLY TO SOL PROTEIN, IE THE HEMOGLOBIN BETA CHAIN.|BROMOBENZENE YIELDS N-ACETYL-S-(4-BROMO-1,2-DIHYDRO-2-HYDROXYPHENYL)-L-CYSTEINE IN RABBIT & RAT; N-ACETYL-S-(P-BROMOPHENYL)-L-CYSTEINE IN DOG & IN MOUSE. /FROM TABLE/|BROMOBENZENE MAY BE METABOLIZED TO AN EPOXIDE...EXCRETED IN BILE, REABSORBED THROUGH ENTEROHEPATIC CIRCULATION, & METABOLIZED IN SEVERAL STEPS TO S-P-BROMOPHENYL MERCAPTURIC ACID, WHICH IS THEN EXCRETED IN URINE.|For more Metabolism/Metabolites (Complete) data for BROMOBENZENE (13 total), please visit the HSDB record page.

0.06 Days

FOLLOWING BROMOBENZENE (1.0 MMOL) ADMIN TO RAT HEPATOCYTES, LIPID PEROXIDATION OCCURRED ONLY AT A LATER STAGE, COMPARED TO TREATMENT WITH CCL4, AND ONLY AFTER CELL DEATH. APPARENTLY LIPID PEROXIDATION DURING BROMOBENZENE TOXICITY WAS MERELY A CONSEQUENCE OF GSH DEPLETION AND CELL DEATH. APPARENTLY, ARYLATION OF CRITICAL CELLULAR NUCLEOPHILES IS MORE IMPORTANT THAN LIPID PEROXIDATION IN BROMOBENZENE HEPATOTOXICITY.|FRESHLY ISOLATED HEPATOCYTES FROM PHENOBARBITAL-TREATED RATS WERE INCUBATED IN THE PRESENCE OR ABSENCE OF EXTRACELLULAR CALCIUM WITH BROMOBENZENE. IN THE ABSENCE OF CALCIUM IT WAS FAR MORE TOXIC TO THE CELLS THAN IN ITS PRESENCE. THIS RESULT IS INCONSISTENT WITH THE HYPOTHESIS THAT AN INFLUX OF EXTRACELLULAR CALCIUM IS REQUIRED AS THE FINAL STEP IN TOXIC LIVER CELL INJURY.|A NOVEL METHOD IS DESCRIBED FOR MEASURING THE COVALENT BINDING OF BROMOBENZENE TO MACROMOLECULES IN RAT HEPATIC MICROSOMES OF HEPATOCYTES. COVALENT BINDING IN HEPATOCYTES SUGGESTS THAT THE BINDING OCCURS FIRST WITH MACROMOLECULES IN 20000-40000 DALTON RANGE.

Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach. (USCG, 1999)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

IRRITANT TO SKIN. HIGH VAPOR CONCN MAY BE ANESTHETIC.|HEPATIC CENTRILOBULAR NECROSIS INDUCED BY BROMOBENZENE IS THOUGHT TO BE CAUSED BY FORMATION OF BROMOBENZENE.../SRP: OXIDES & THEIR/ SUBSEQUENT REACTION WITH LIVER PROTEINS, THE PRODUCTS OF WHICH CAN BE FOUND IN NECROTIC AREAS OF LIVER.|...NO EVIDENCE THAT BROMOBENZENE IS CARCINOGENIC IN...MAN.

bromobenzene

The substance can be absorbed into the body by inhalation and by ingestion.

Dizziness.


Redness.

Bromobenzene Use and Manufacturing

Methods of Manufacturing

The preparation method is to use benzene to react with bromine, and use iron powder as a catalyst for bromination. After adding bromine, the reaction is kept at 70-80℃ for 1 hour, and then washed, dried, and distilled to obtain the product.

Uses

In organic synthesis, especially to make phenyl magnesium bromide; as solvent, especially for crystallizations on a large scale and where a heavy liquid is desirable; as additive to motor oils.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) GREATER THAN 4.5X10+5 GRAMS

GRADES: TECHNICAL; PURE.

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

NEGATIVE ION CHEM IONIZATION MASS SPECTROMETRY IS EVALUATED AS A METHOD FOR QUAL AND QUANT DETN OF POLYHALOGENATED AROMATIC HYDROCARBONS, INCL BROMOBENZENE.|THE OCTANOL/WATER PARTITION COEFFICIENT OF BROMOBENZENE IS DETERMINED BY REVERSE PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY.|BROMOBENZENE IS DETECTED IN DRINKING WATER BY GAS CHROMATOGRAPHY USING THE PURGE-AND-TRAP METHOD. DETECTION LIMITS ARE APPROX 0.1 UG/L.|ORGANOHALIDES FROM NATURAL WATER SAMPLES WERE MEASURED BY DIRECT POTENTIOMETRY OR BY POTENTIOMETRIC TITRATION.|For more Analytic Laboratory Methods (Complete) data for BROMOBENZENE (14 total), please visit the HSDB record page.

Fire Hazards -> Flammable - 2nd degree

Computed Properties

Molecular Weight:157.01
XLogP3:3
Exact Mass:155.95746
Monoisotopic Mass:155.95746
Heavy Atom Count:7
Complexity:46.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

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