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Bromobenzene
ブロモベンゼン (1mg/mlメタノール溶液) [水質分析用] · 1-ブロモベンゼン · 3-ブロモベンゼン · ブロモベンゾール · フェニルブロミド · 4-ブロモベンゼン · 臭化フェニル · ブロモベンゼン ブロモ 臭化物
識別子と物理属性
| CAS No. | 108-86-1 |
|---|---|
| 分子式 | C6H5Br |
| 平均分子量 | 157.01 g/mol |
| 単同位体質量 | 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 |
| 現地名 | ブロモベンゼン |
化学・物理的性質
| XLogP | 3 |
|---|---|
| 極性表面積 | 0 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 7 |
| 形式電荷 | 0 |
| 複雑度 | 46.1 |
| 物質分類 | Flammable agents - 2nd degreeVolatile Organic Compound (VOC) |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = 2.99 |
| 臭い | AROMATIC ODORPungent odor楽しい。 |
| 密度 | 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 |
| 溶解度 | 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 °Cジエチルエーテル、アルコール、四塩化炭素、クロロホルム、ベンゼンと混和します。不溶。 <0.1 g/100 mL で 20.5 ºC |
| 引火点 | 123.8 °F (NTP, 1992)Flash point equals 124 °F51 °C (124 °F) (CLOSED CUP)51 °C c.c. |
| 沸点 | 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.) |
| 融点 | -31 °C |
| 蒸気密度 | 5.41 (vs air) |
| 蒸気圧 | 10 mm Hg ( 40 °C) |
| 屈折率 | n20/D 1.559(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 液体 |
| 色 | 無色透明～微黄色 |
| 爆発限界 | 0.5-2.5%(V) |
| 比熱容量 | Cp(liquid): 0.98 J/(g·K), at 25℃ |
| Merck | 14,1406 |
| BRN | 1236661 |
| ヘンリー定数 | 2.47 at 25 °C (gas stripping-GC, Shiu and Mackay, 1997) |
| 誘電率 | 5.4(20℃) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChI | 1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H |
| InChIKey | QARVLSVVCXYDNA-UHFFFAOYSA-N |
| SMILES | Brc1ccccc1 |
| LogP（分配係数） | 3.14 at 25℃ |
| 表面張力 | 33.5mN/m at 303.15K |
| CAS データベース | 108-86-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzene, bromo-(108-86-1) |
| EPAの化学物質情報 | Bromobenzene (108-86-1) |
化学的特性
Bromobenzene, also known as phenyl bromide and monobromobenzene, is a benzene halogen derivative generated by benzene being substituted by bromine in the presence of iron powder. The chemical reaction principle is the same as that of chlorination of benzene to produce chlorobenzene. The reaction between bromobenzene and metal magnesium can generate phenylmagnesium bromide, which is a Grignard reagent with important uses in organic synthesis.
安全性と法規制
| GHS 分類 | 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] |
|---|---|
| 規制情報 | 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.) |
| その他の安全情報 | IMAP assessments - Benzene, bromo-: Human health tier I assessment |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | 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. |
| 火災の可能性 | MODERATE, WHEN EXPOSED TO HEAT OR FLAME... |
| 健康有害性 | 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. |
| 有害性の概要 | 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] |
| 輸送番号・ガイド（DOT） | 2514 130 |
| 反応性グループ | Aryl Halides |
| EC 分類 | Symbol: Xi, NR: 10-38-51/53S: (2)-61 |
| UN 分類 | UN Hazard Class: 3UN Pack Group: III |
| TSCA 要件 | 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. |
| 消火 | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| 応急処置措置 | 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 . |
| 漏出応急措置 | · 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. |
| 応急処置 | 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: |
| 安全保管 | 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. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | 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. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: |
| 処分方法 | 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. |
| 漏出処分 | 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. |
| 体内負荷 | 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. |
| 相互作用 | ...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. |
| 標的器官 | Hepatic |
| 健康影響 | 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). |
| 環境中動態 | 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). |
| 食品調査値 | 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. |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion.Oral (L626)inhalation (L626)dermal (L626) |
| 毒性の概要 | 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] |
| 州飲料水ガイドライン | (FL) FLORIDA 4,000 ug/l |
| 連邦飲料水ガイドライン | EPA 70 ug/L |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | CY9000000 |
| 輸送番号（UN） | UN 2514 |
| 毒性 | LD50 orally in Rabbit: 2383 mg/kg |
| 税関コード | 2903 99 80 |
| 危険文句（R） | 10-38-51/53-39/23/24/25-23/24/25 |
| 化審法 | (3)-32 |
| 消防法 | 危-4-2-III |
| 危険表示 | Xi,N,F,T |
| 安全措置（S） | 61-45-36/37 |
| 危険等級 | 3Aquatic Chronic 2Flam. Liq. 3Skin Irrit. 2 |
| 包装等級 | III |
| 自然発火温度 | 565 °C |
| 貯蔵分類 | 3 - Flammable liquids |
| 有害物質データ | 108-86-1(Hazardous Substances Data) |
用途
解説
ブロモベンゼン，液体．融点－31 ℃，沸点155～156 ℃，43 ℃(2.4 kPa)．d1515"1.4991．nD15"1.5625．エタノール，エーテルに可溶．ベンゼン，石油系炭化水素などとまざる．臭化ベンゼンマグネシウムはグリニャール試薬として，各種のベンゼン誘導体の合成に使われる．そのほか溶剤に用いられる．高濃度では麻酔性があり，皮膚を刺激する．森北出版「化学辞典（第2版）
用途
難燃剤、医薬、農薬、香料の中間体、染料、電動機油添加剤として用いられる。
用途
難燃剤、医薬 農薬 香料の中間体
使用
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.
製法・合成法
製造方法
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.
合成方法
鉄粉存在下，ベンゼンに臭素を反応させて製造される
純化方法
Wash bromobenzene vigorously with conc H2SO4, then 10% NaOH or NaHCO3 solutions, and H2O. Dry it with CaCl2 or Na2SO4, or pass it through activated alumina, before refluxing with, and distilling from, CaH2, using a glass helix-packed column. [Beilstein 5 IV 670.]