Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
o-브로모톨루엔
2-브로모톨루엔 · o-브로모톨루엔 · 2-브로모토루엔 · 1-BROMO-2-METHYLBENZENE · a13-26648 · 2-Bromtoluol · o-bromo-toluen · 2-BROMOTOLUENE
식별자 및 물리적 특성
| CAS No. | 95-46-5 |
|---|---|
| 분자식 | C7H7Br |
| 평균 분자량 | 171.03 g/mol |
| 단동위원소 질량 | 169.97311232 g/mol |
| SMILES | Cc1ccccc1Br |
| InChIKey | QSSXJPIWXQTSIX-UHFFFAOYSA-N |
| PubChem CID | 7236 |
| ChEMBL | CHEMBL1339978 |
| EC No. | 202-421-7 |
| DTXSID | DTXSID2024660 |
| 현지명 | o-브로모톨루엔 |
화학 및 물리적 성질
| XLogP | 3.5 |
|---|---|
| 극성 표면적 | 0 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 0 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 8 |
| 형식 전하 | 0 |
| 복잡도 | 70.8 |
| Solvents | Solvents -> Brominated Solvents |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP(분배 계수) | log Kow = 3.50 |
| 밀도 | 1.431 at 59 °F (NTP, 1992) - Denser than waterwill sink1.432 @ 20 °C/4 °C1.422 g/mL at 25 °C (lit.) |
| Color/Form | COLORLESS LIQ |
| 용해도 | less than 1 mg/mL at 59 °F (NTP, 1992)PRACTICALLY INSOL IN WATERSOL IN ALL PROPORTIONS IN CARBON TETRACHLORIDEVery soluble in ethanol, ether, and benzene |
| 인화점 | 174 °F (NTP, 1992)79 °C79 °C (174 °F) CLOSED CUP |
| 끓는 점 | 358 °F at 760 mmHg (NTP, 1992)181.7 °C58-60 °C/10 mmHg (lit.) |
| 녹는점 | -15 °F (NTP, 1992)-27.8 °C-27 °C (lit.) |
| 증기 밀도 | 5.9 (Air= 1) |
| 증기압 | 1 mmHg at 75.9 °F (NTP, 1992)1.04 [mmHg]Vapor pressure = 2.88 kPa (21.6 mm Hg) at 75 °C1.00 mm Hg @ 25 °C /Calculated from experimentally-derived coefficients/ |
| 굴절률 | INDEX OF REFRACTION: 1.5565 AT 20 °C/Dn20/D 1.555(lit.) |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 액체 |
| 비중 | 1.422 |
| 색상 | 무색투명~연황색 |
| 용해도 | 15°C에서 <0.1g/100mL |
| Merck | 14,1439 |
| BRN | 1904176 |
| 헨리 상수 | 4.1×10-3 mol/(m3Pa) at 25℃, HSDB (2015) |
| 유전율 | 4.2800000000000002 |
| 안정성 | 안정적인. 강한 산화제와 호환되지 않습니다. |
| InChI | 1S/C7H7Br/c1-6-4-2-3-5-7(6)8/h2-5H,1H3 |
| InChIKey | QSSXJPIWXQTSIX-UHFFFAOYSA-N |
| SMILES | Cc1ccccc1Br |
| NIST | Benzene, 1-bromo-2-methyl-(95-46-5) |
| EPA | o-Bromotoluene (95-46-5) |
화학적 성질
liquid
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H227: Combustible liquid [Warning Flammable liquids] |
|---|---|
| 규제 정보 | Chemical: Benzene, 1-bromo-2-methyl-2-Bromotoluene: Does not have an individual approval but may be used under an appropriate group standard |
| 운송 라벨(DOT) | Corrosive |
| 화재 위험 | This chemical is combustible. (NTP, 1992) |
| 건강 유해성 | SYMPTOMS: This compound causes skin and eye irritation. |
| 유해성 요약 | May cause liver injury[HSDB] A skin and eye irritant[CAMEO] An irritant[MSDSonline]The major hazards encountered in the use and handling of 2-bromotoluene stem from its toxicologic properties. Exposure to this colorless liquid may occur through inhalation or dermal contact at sites where the substance is manufactured, used as a solvent, or used as a chemical intermediate. This substance is considered to be hazardous to health with the potential to cause respiratory irritation, CNS depression, and hepatotoxicity. Entry into contaminated areas warrants the wearing of a full-face mask, self-contained breathing apparatus which provides eye protection. This substance is normally stable, even under fire exposure conditionsrequiring moderate heating before ignition will occur (flash point 79 °C, closed cup). Normal procedures may be used to fight a 2-bromotoluene fireextinguishing with water spray that blankets the fire and cools the substance below its flash point. Before transporting 2-bromotoluene, the regulatory requirements of the DOT must be consulted. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance. |
| 반응성 그룹 | Aryl Halides |
| Reactivity Profile | O-BROMOTOLUENE reacts with strong oxidizing agents. (NTP, 1992) |
| Air and Water Reactions | Insoluble in water. |
| NFPA Hazard Classification | 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Flammable liquids - Category 4 |
| Shipment Methods and Regulations | 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. |
| Skin, Eye, and Respiratory Irritations | Irritant |
| 소화 | Fires involving this material can be controlled with a dry chemical, carbon dioxide, or a Halon extinguisher. (NTP, 1992) |
| 응급 처치 | 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. |
| 비화재 누출 대응 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 처리 방법 | 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. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| 환경 거동 | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 443(SRC), derived from a molecular structure estimation method(2), suggests that 2-bromotoluene will have moderate mobility in soil(SRC). Its high estimated Henry's Law constant, 2.4X10-3 atm-cu m/mole(3), high vapor pressure, 1.0 mm Hg at 25 °C(5), and moderate adsorptivity to soil indicates that volatilization may be an important fate process from both moist and dry soil surfaces(4,SRC). Experimental data suggest that 2-bromotoluene may be subject to direct photolysis on the soil surface(6). 2-Bromotoluene's potential for biodegradation in soil is unknown.AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 443(SRC) determined from molecular structure(2), indicates that 2-bromotoluene may adsorb to sediment and particulate matter in the water column(SRC). It is expected to readily volatilize from water based on its estimated Henry's Law constant of 2.4X10-3 atm-cu m/mole(3). Estimated half-lives for a model river and model lake are 4.3 hours and 5.3 days, respectively(4,SRC). Using a model which takes adsorption into account(8), the volatilization half-life of 2-bromotoluene in an environmental pond is estimated to be 14.9 days. Experimental data suggests that 2-bromotoluene may be subject to direct photolysis in surface waters(7). Its potential for biodegradation is unknown. According to a recommended classification scheme(6), an estimated BCF value of 270(4,SRC), based on its log Kow(5,SRC), suggests that bioconcentration in aquatic organisms will be moderately high(SRC).ATMOSPHERIC FATE: According to a theory of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-bromotoluene has a vapor pressure of 1.0 mm Hg at 25 °C(1). Based on this vapor pressure, 2-bromotoluene should exist entirely in the vapor phase in the ambient atmosphere(2,SRC). Vapor phase 2-bromotoluene should degrade in the atmosphere by reaction with photochemically produced hydroxyl radicalsthe half-life for this reaction is estimated to be 9.8 days(3,SRC). |
| 유해 작용 | Neurotoxin - Acute solvent syndrome |
| Soil Adsorption/Mobility | Using an estimation method based on molecular connectivity indices(1), the Koc for 2-bromotoluene is estimated to be 440(SRC). According to a suggested classification scheme(2), this Koc value suggests that 2-bromotoluene will have medium mobility in soil(SRC). |
| Artificial Pollution Sources | Bromotoluene may be released to the environment in waste streams and as emissions during its use as a solvent (for fats, waxes or resins, and as a medium for carrying out reactions) and as chemical intermediate(1,2). Use of 2-bromotoluene as a solvent may result in direct environmental release through evaporation. Environmental releases may also be possible from wastes generated at sites of production or use as a chemical intermediate(SRC). |
| Environmental Bioconcentration | A BCF of 270 was estimated for 2-bromotoluene(SRC), using its estimated log Kow of 3.43(1,SRC), and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in fish and aquatic organisms will be moderately high(SRC). |
| Volatilization from Water/Soil | Based upon a quantitative structure analysis relationship (QSAR) estimation method, the Henry's Law constant of 2-bromotoluene is estimated to be 2.4X10-3 atm-cu m/mole at 25 °C(1,SRC). This value of Henry's Law constant indicates that volatilization from environmental waters is probably significant, and may be rapid(2). The volatilization half-lives of 2-bromotoluene from a model river (1 meter deep flowing 1 m/sec with a wind speed of 3 m/sec) and model lake (1 meter deep flowing at 0.05 m/sec with a wind speed of 0.5 m/sec) are estimated to be 4.3 hr and 5.3 days, respectively(2,SRC)these estimates do not consider the effect of adsorption to sediment which may be important(SRC). The volatilization half-life of 2-bromotoluene in an experimental pond which considers adsorption has been estimated to be 14.9 days(3,SRC). |
| Non-Human Toxicity Excerpts | RELATIVE HEPATOTOXICITY OF O-BROMOBENZONITRILE, BROMOBENZENE, O-BROMOTOLUENE & O-BROMOBENZOTRIFLUORIDE IN RATS DECR IN ORDER GIVEN.SERIES OF 7 O-SUBSTITUTED BROMOBENZENES INCLUDING 2-BROMOTOLUENE WERE EVALUATED FOR THEIR POTENTIAL TO PRODUCE LIVER INJURY IN RATS, AS REFLECTED IN HISTOLOGICAL OBSERVED CENTRILOBULAR NECROSIS & INCR IN SERUM GLUTAMATE-PYRUVATE TRANSAMINASE. EACH COMPOUND (INCLUDING 0.15 ML/KG 2-BROMOTOLUENE) WAS ADMIN IP. TWENTY-FOUR HR TOXICTY VALUES FOR THE COMPOUNDS WERE SIMILAR FOR BOTH INDEXES OF LIVER DAMAGE & INDICATED THAT BROMOBENZENES BEARING ELECTRON WITHDRAWING SUBSTITUENTS AT THE ORTHO POSITION ARE VERY POTENT LIVER TOXICANTS. BROMOBENZENES WITH ELECTRON-RELEASING SUBSTITUENTS ARE LESS TOXIC, & THOSE BEARING SUBSTITUENTS WITH LESS PRONOUNCED ELECTRONIC CHARACTER ELICITED INTERMEDIATE TOXIC EFFECTS.o-Bromotoluene tested negative for mutagenicity in Salmonella assays.Liver slices in an organ culture system were used to examine the relationships between relative metabolism, covalent binding and toxicity of a series of bromobenzene derivatives. Liver slices from male Sprague-Dawley rats were incubated with toxic concentrations of bromobenzene and bromobenzene derivatives dual labeled with tritium and (14)C. The bromobenzene derivatives used were o-bromoanisole, o-bromotoluene, o-bromobenzonitrile, and o-dibromobenzene. Incubations were conducted at various times (2 to 24 hr for measurement of total metabolism and total covalent binding. No correlation between metabolism and toxicity was observed among the compounds studied. Covalent binding varied 7 fold across the series, and those compounds which bound the most frequently were the most toxic. The relative binding index (RBI) for each compound and the average retention of tritium relative to (14)C in the covalent binding fraction were constant through the 24 hour incubation periods. This finding suggests that the metabolic profile of each compound was constant over time. The pool bound/nom metabolism values did not reflect relative toxicity as well as did the total covalent binding values.For more Non-Human Toxicity Excerpts (Complete) data for 2-BROMOTOLUENE (7 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 2-bromotoluene with photochemically produced hydroxyl radicals has been estimated to be 1.64X10-12 cu m/molecule-sec at 25 °C(1,SRC)assuming an average atmospheric hydroxyl radical concn of 5X10+5 molecules/cu cm, the half-life for this reaction can be estimated to be 9.8 days(1,SRC). 2-Bromotoluene does not contain any functional groups that are susceptible to aqueous environmental hydrolysis(2)therefore, hydrolysis is not expected to be significant in water(SRC). Irradiation of 2-bromotoluene (in hexane solution) with artificial UV light above 290 nm resulted in a dehalogenation of 1.03% over a two hour period(3). |
| Probable Routes of Human Exposure | Occupational exposure may occur through inhalation or dermal contact at sites where 2-bromotoluene is manufactured, used as a solvent or used as a chemical intermediate. (SRC) |
| Environmental Fate/Exposure Summary | 2-Bromotoluene may be released to the environment through evaporation from solvent uses or from wastes generated at sites of production and use. If released to the atmosphere, 2-bromotoluene is expected to degrade by reaction with photochemically produced hydroxyl radicalsthe half-life for this reaction is estimated to be 9.8 days. If released to water, 2-bromotoluene may be removed from the water column by volatilization and adsorption. Using an estimated Henry's Law constant of 2.4X10-3 atm-cu m/mol, volatilization half-lives of 4.3 hr and 5.3 days can be estimated for a model river (1 m deep) and model lake, respectively. The potential effect of adsorption to sediment is considered in the half-life from an environmental pond which is estimated to be 14.9 days, but not from the model river or model lake. An estimated Koc of 440 suggests that if 2-bromotoluene is released to soil, moderate leaching may occur. Based on its estimated Henry's Law constant and measured vaopr pressure (1mm Hg at 25 °C), evaporation from dry and moist soil surfaces may also occur. Data are not available with which to assess the importance of biodegradation in the environment. Its estimated BCF of 270 suggests that there is a moderately high potential for bioaccumulation in aquatic organisms. Occupational exposure may occur through inhalation or dermal contact at sites where 2-bromotoluene is manufactured, used as a solvent or used as a chemical intermediate. (SRC) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | XS7965500 |
| 관세 코드 | 29036990 |
| 위험 문구(R) | 22-36/37/38 |
| 위험 표시 | Xn,Xi |
| 안전 문구(S) | 36/37/39-37/39-26 |
| 포장분류 | III |
| 위험 참고 사항 | Harmful/Irritant |
| 위험 등급 | Acute Tox. 4 OralAquatic Chronic 2 |
| 저장 분류 | 10 - Combustible liquids |
| 유해 물질 데이터 | 95-46-5(Hazardous Substances Data) |
용도
용도
2-Bromotoluene was used in the synthesis of (±)-isocomene. Suzuki coupling of 2-bromotoluene with phenylboronic acid using palladium nanoparticles supported on alumina-based oxides as catalyst has been reported. 2-Bromotoluene is used in manufacturing pharmaceuticals (especially for nonsteroidal antiinflammatory drugs; Meclofenamic acid, Mefenamic acid) and other organic compounds
일반 설명
Clear colorless to pale beige liquid.