HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bromobenzene
1-Bromobenzene · PHENYL BROMIDE · Brombenzol · Bromobenzol · 4-Bromobenzene · MONOBROMOBENZENE · bromo-benzen · Benzene,bromo-
Identifiers & Physical Properties
| CAS No. | 108-86-1 |
|---|---|
| Molecular formula | C6H5Br |
| Average molar mass | 157.01 g/mol |
| Monoisotopic mass | 155.95746226 g/mol |
| SMILES | Brc1ccccc1 |
| InChIKey | QARVLSVVCXYDNA-UHFFFAOYSA-N |
| PubChem CID | 7961 |
| ChEMBL | CHEMBL16068 |
| ChEBI | CHEBI:3179 |
| EC No. | 203-623-8 |
| DTXSID | DTXSID5024637 |
Chemical & Physical Properties
| XLogP | 3 |
|---|---|
| Topological polar surface area | 0 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 0 |
| Rotatable bonds | 0 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 46.1 |
| Chemical classes | Flammable agents - 2nd degreeVolatile Organic Compound (VOC) |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pesticides | Pesticide -> EPA IRIS |
| LogP (partition coefficient) | log Kow = 2.99 |
| Odor | AROMATIC ODORPungent odorpleasant smell |
| Density | 1.49 at 77 °F (USCG, 1999) - Denser than waterwill sink@ 10 °C/4 °C: 1.5083@ 15 °C/4 °C: 1.5017@ 20 °C/4 °C: 1.4952@ 30 °C/4 °C: 1.4815@ 71 °C/4 °C: 1.426@ 0 °C/4 °C: 1.5220Relative density (water = 1): 1.51.495 @ 20°C1.491 g/mL at 25 °C(lit.) |
| Viscosity | 1.124 CP @ 20 °C |
| Color/Form | MOBILE LIQUIDHeavy, mobile, colorless liquid |
| Solubility | less than 1 mg/mL at 68.9 °F (NTP, 1992)MISCIBLE WITH CHLOROFORM, BENZENE, PETROLEUM HYDROCARBONSSOL IN ALCOHOL (10.4 G/100 G @ 25 °C), IN ETHER (71.3 G/100 G @ 25 °C)PRACTICALLY INOL IN WATER (0.045 G/100 G @ 30 °C)SOL IN CARBON TETRACHLORIDEMiscible with most organic solventsinsoluble in waterVery soluble in ethanol, ethyl ether, and benzeneSolubility in water = 410 mg/l @ 25 °CMiscible with diethyl ether, alcohol, carbon tetrachloride, chloroform and benzene.insoluble. <0.1 g/100 mL at 20.5 ºC |
| Flash point | 123.8 °F (NTP, 1992)Flash point equals 124 °F51 °C (124 °F) (CLOSED CUP)51 °C c.c. |
| Boiling point | 313 °F at 760 mmHg (NTP, 1992)boiling point equals 313 °F156.2 °C @ 760 MM HGBoiling point: 132.3 °C @ 400 mm Hg110.1 °C @ 200 mm Hg68.6 °C @ 40 mm Hg53.8 °C @ 20 mm Hg40.0 °C @ 10 mm Hg27.8 °C @ 5 mm Hg2.9 °C @ 1 mm Hg156.06 °C @760 [mm Hg]156 °C(lit.) |
| Melting point | -31 °C |
| Vapor density | 5.41 (vs air) |
| Vapor pressure | 10 mm Hg ( 40 °C) |
| Refractive index | n20/D 1.559(lit.) |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| Color | Clear colorless to faintly yellow |
| Explosive limits | 0.5-2.5%(V) |
| Thermal conductivity | 0.111 W/(m·K) at 25 ℃ |
| Specific heat capacity | Cp(liquid): 0.98 J/(g·K), at 25℃ |
| Merck | 14,1406 |
| BRN | 1236661 |
| Henry's law constant | 2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997) |
| Dielectric constant | 5.4(20℃) |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H |
| InChIKey | QARVLSVVCXYDNA-UHFFFAOYSA-N |
| SMILES | Brc1ccccc1 |
| LogP (partition coefficient) | 3.14 at 25℃ |
| Surface tension | 33.5mN/m at 303.15K |
| CAS DataBase Reference | 108-86-1(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| FDA UNII | CO4D5J547L |
| NIST Chemistry Reference | Benzene, bromo-(108-86-1) |
| EPA Substance Registry System | Bromobenzene (108-86-1) |
| UNSPSC Code | 12352101 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS07,GHS08,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H303-H315-H373-H411-H226 |
| GHS precautionary statements | P501-P273-P240-P260-P210-P233-P243-P241-P242-P264-P280-P370+P378-P312-P391-P362+P364-P303+P361+P353-P332+P313-P403+P235 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi,N,F,T |
| Risk statements (R) | 10-38-51/53-39/23/24/25-23/24/25 |
| Safety statements (S) | 61-45-36/37 |
| UN transport number | UN 2514 |
| Water hazard class (WGK) | 2 |
| RTECS number | CY9000000 |
| Autoignition temperature | 565 °C |
| TSCA inventory status | TSCA listed |
| Customs code | 2903 99 80 |
| Hazard class | 3Aquatic Chronic 2Flam. Liq. 3Skin Irrit. 2 |
| Packing group | III |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 108-86-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 2383 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | WarningH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P264, P273, P280, P302+P352, P303+P361+P353, P321, P332+P317, P362+P364, P370+P378, P391, P403+P235, and P501 (click each P-code to see the statement)H226 (100%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatory information | Chemical: Benzene, bromo-Benzene, bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, bromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 27-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/19680Bromobenzene: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Other safety information | IMAP assessments - Benzene, bromo-: Human health tier I assessment |
| DOT label | Flammable Liquid |
| Fire hazards | Special Hazards of Combustion Products: Irritating hydrogen bromide and other gases may be produced in fire. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Above 51 °C explosive vapour/air mixtures may be formed. |
| Fire potential | MODERATE, WHEN EXPOSED TO HEAT OR FLAME... |
| Health hazards | Contact with liquid causes irritation of eyes and mild irritation of skin. Ingestion causes mild irritation of mouth and stomach. (USCG, 1999)· May cause toxic effects if inhaled or absorbed through skin. |
| Hazards summary | A skin and eye irritant[CAMEO] Anesthetic properties at high concentrationsToxic to the liver in animal studiesVery toxic by ingestion with an estimated lethal dose of 50-500 mg per kilogram[HSDB] |
| DOT ID and guide | 2514 130 |
| Reactive group | Aryl Halides |
| EC classification | Symbol: Xi, NR: 10-38-51/53S: (2)-61 |
| UN classification | UN Hazard Class: 3UN Pack Group: III |
| TSCA requirements | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Bromobenzene is included on this list. |
| Fire fighting | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| First aid measures | 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.Do NOT induce vomiting. Refer for medical attention . |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | 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.General First Aid: |
| Safe storage | Fireproof. Ventilation along the floor. |
| Firefighting Hazards | 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. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Fire fighting procedures | 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. |
| Nonfire spill response | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: |
| Disposal methods | 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. |
| Spillage disposal | 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. |
| Preventive Measures | 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. |
| Body burden | 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). |
| Treatment | EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration. |
| Interactions | ...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. |
| Target organs | Hepatic |
| Health effects | The toxic effects of bromobenzene following acute exposure have been extensively studied in animals. Liver, kidney, and lung have been identified as the target organs for this chemical by a variety of routes. It can cause liver and nervous system damage if inhaled, ingested, or absorbed through the skin (L1987). |
| Environmental fate | 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 biodegradationafter 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 biodegradationATMOSPHERIC 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). |
| Food survey values | 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. |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by inhalation and by ingestion.Oral (L626)inhalation (L626)dermal (L626) |
| Toxicity summary | The hepatotoxicity of bromobenzene is due to the production of reactive metabolites that modify or alkylated DNA, RNA and proteins. These reactive metabolites arise from the action of the CYP enzymes that are concentrated in the liver that lead to the production of cytotoxic compounds such as the 2,3- and 3,4-oxides of bromobenzene, the oxides of the bromophenols, 1,4-benzoquinone, and the radicals and quinones derived from redox cycling of the 2- and 4-bromocatechols. Similar reactive metabolites lead to renal damage, albeit at higher doses. |
| Signs and Symptoms | Dizziness.Redness.Nausea. Diarrhoea.If inhaled, bromobenzene causes irritation to the respiratory tract. Symptoms may include coughing, shortness of breath. Affects central nervous system causing dizziness, incoordination and unconsciousness. May be absorbed into the bloodstream with symptoms similar to ingestion. If the compound is ingested it can cause abdominal pain, nausea, vomiting, diarrhea, headache, dullness, central nervous system effects and liver damage. Estimated lethal human dose is 50 - 500 mg/kg. Contact with skin or eyes causes irritation, redness and pain. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=108-86-1] |
| State drinking water guidelines | (FL) FLORIDA 4,000 ug/l |
| Federal drinking water guidelines | EPA 70 ug/L |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | CY9000000 |
| UN transport number | UN 2514 |
| Customs code | 2903 99 80 |
| Toxicity | LD50 orally in Rabbit: 2383 mg/kg |
| Risk statements (R) | 10-38-51/53-39/23/24/25-23/24/25 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS07,GHS08,GHS09 |
| Hazard symbols | Xi,N,F,T |
| Safety statements (S) | 61-45-36/37 |
| Hazard class | 3Aquatic Chronic 2Flam. Liq. 3Skin Irrit. 2 |
| Storage class | 3 - Flammable liquids |
| Packing group | III |
| GHS hazard statements | H303-H315-H373-H411-H226 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 565 °C |
| GHS precautionary statements | P501-P273-P240-P260-P210-P233-P243-P241-P242-P264-P280-P370+P378-P312-P391-P362+P364-P303+P361+P353-P332+P313-P403+P235 |
| Hazardous substances data | 108-86-1(Hazardous Substances Data) |
Applications & Uses
Description
Bromobenzene is a flammable, clear, colorlessmobile liquid with a pleasant odor. Molecularweight=157.02. Specific gravity (H2O:1)=1.48; Boilingpoint=156℃; Freezing/Melting point=2 31℃; Flashpoint=51℃; Autoignition temperature=565℃. Explosivelimits in air: LEL=6%; UEL=36.5%[icsc]. HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 2, Reactivity 0. Very slightly soluble in water; solubility=0.04% at 25℃.
Uses
Bromobenzene is an additive to motor oils and used as a crystallizing solvent. It is used as an ingredient in the manufacture of phencyclidine, a recreational drug.
Preparation & Synthesis
Preparation
Bromobenzene is obtained by reacting benzene with bromine. First add iron powder and benzene into the reactor, slowly add bromine under stirring, keep the reaction at 70-80°C for 1 h after adding, the obtained crude product is washed with water and 5% sodium hydroxide solution, left to stand for stratification, distillation, Drying, filtering, and finally fractional distillation under constant pressure, taking the fraction at 155-157°C to obtain the finished product.