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HCID 7498생성일: 2026년 10월 23일

벤질브로마이드

벤질브롬화물 · 벤질브로마이드 · 브롬화벤질 · 벤질 브로마이드 · BnBr · bromomethylbenzene · cyclite · 1-Bromotoluene

https://huagongshe.com/ko/chemical/7498

벤질브로마이드 분자 구조식

식별자 및 물리적 특성

CAS No.100-39-0
분자식C7H7Br
평균 분자량171.03 g/mol
단동위원소 질량169.97311232 g/mol
SMILESBrCc1ccccc1
InChIKeyAGEZXYOZHKGVCM-UHFFFAOYSA-N
PubChem CID7498
ChEMBLCHEMBL1085946
ChEBICHEBI:59858
EC No.202-847-3
DTXSIDDTXSID8024658
현지명벤질브로마이드

화학 및 물리적 성질

XLogP2.9
극성 표면적0
수소 결합 공여자 수0
수소 결합 수용자 수0
회전 가능 결합 수1
무거운 원자 수8
형식 전하0
복잡도55.4
물질 분류Other Classes -> Halogenated MonoaromaticsCorrosives
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP(분배 계수)log Kow = 2.92
냄새Very sharppungentlike tear gas최루탄처럼 매우 날카롭고 자극적입니다.
밀도1.441 at 71.6 °F (USCG, 1999) - Denser than waterwill sink1.4380 at 20 °CRelative density (water = 1): 1.4381.738 @25 °C1.44 g/mL at 20 °C
Color/FormClear, refractive liquidColorless to yellow liquidLacrimatory liquid
용해도Reaction (NTP, 1992)Miscible in ethanol and ethersoluble in carbon tetrachlorideSol in benzeneSolubility in water: reaction벤젠, 사염화탄소, 에탄올 및 에테르와 혼합 가능합니다.
CorrosivityCorrosive to metal ... .
인화점188 °F (NTP, 1992)79 °C86 °C (187 °F) - closed cup79 °C (closed cup)79 °C c.c.
끓는 점388 to 390 °F at 760 mmHg (NTP, 1992)191 °C198-199 °C201 °C @760 [mm Hg]198-199 °C(lit.)
DecompositionThe substance decomposes slowly on contact with water producing hydrogen bromide.When strongly heated, they emit highly toxic fumes of /hydrogen bromide/. /bromides/On combustion, forms toxic fumes including hydrogen bromide.
녹는점27 to 30 °F (NTP, 1992)-1.5 °C-4.0 °C-3 °C
증기 밀도5.8 (vs air)
증기압0.5 hPa (20 °C)
굴절률n20/D 1.575(lit.)
저장 조건Store below +30°C.
물리적 상태액체
색상무색~황색으로 투명함
Merck14,1128
BRN385801
헨리 상수1.4×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
유전율5.1(20℃)
안정성안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다.
InChI1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
InChIKeyAGEZXYOZHKGVCM-UHFFFAOYSA-N
SMILESBrCc1ccccc1
NISTBenzene, (bromomethyl)-(100-39-0)
EPABenzyl bromide (100-39-0)

화학적 성질

Benzyl bromide is an aromatic compound in which the benzene ring substituted with a bromomethyl group, and is produced by the reaction of toluene with bromine in the presence of an oxidizing agent. It is a combustible, colorless to yellow liquid with a pleasant odor. insoluble in water and easily soluble in most organic solvents. Has a strong tearing effect and unpleasant pungent odor, minimum irritant concentration of 4 mg/m3, intolerable concentration of 50-60 mg/m3.

안전 및 규제

GHS 분류WarningH315: Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)H315 (99.2%): Causes skin irritation [Warning Skin corrosion/irritation]
규제 정보Chemical: Benzene, (bromomethyl)-Status: Active Update: 07-08-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/23901Benzyl bromide: 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.)
기타 안전 정보IMAP assessments - Benzene, (bromomethyl)-: Human health tier I assessment
운송 라벨(DOT)Poison Corrosive
화재 위험Special Hazards of Combustion Products: Irritating hydrogen bromide gas may be formed.· Combustible material: may burn but does not ignite readily.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79 °C explosive vapour/air mixtures may be formed.
화재 가능성Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
건강 유해성Inhalation causes irritation of nose and throatsevere exposure may cause pulmonary edema. Vapors cause severe eye irritationliquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
유해성 요약A severe skin, eye, and respiratory tract irritantSkin contact can cause redness and painA lachrymator[ICSC] May cause pulmonary edema[HSDB] Causes lacrimationHigh concentrations can cause CNS depression[Merck Index] Causes skin and eye burnsMay be harmful if ingested, absorbed through skin, or inhaled[MSDSonline]The major hazards encountered in the use and handling of benzyl bromide stem from both its toxicologic and physical/chemical properties. Toxic by all routes (ie, oral, dermal, inhalation), exposure to benzyl bromide may occur environmentally from inhaling air contaminated by exhaust from automobiles using leaded gasoline, or occupationally from its use in research. This colorless to slightly yellow liquid is an intense irritant to skin, eyes, and mucous membranesand, in large doses, can cause CNS depression. Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of the pungent smelling, benzyl bromide. If contact is anticipated (eg, if handling broken benzyl bromide containers), wear a self-contained breathing apparatus, goggles, rubber gloves, and full protective clothing. Any material which contacts the body must be washed away with copious amounts of water. Benzyl bromide does not ignite readily, and burns only with great difficulty. However, when strongly heated, it emits highly toxic fumes and gases. Fire fighters should wear a positive-pressure breathing apparatus and protective clothing, and extinguish benzyl bromide fires with alcohol foam, CO2, or dry chemical agents. Water also may be used particularly in flooding quantities as a spray or fog (solid streams may be ineffective), to reduce vapor and to cool containers. However, care must be taken because benzyl bromide may react with water to form hydrogen bromide gas. Because runoff from fire control water may be toxic or corrosive, it should be diked or otherwise contained. Store benzyl bromide in cool, well-ventilated areas, out of the sun, and away from potential fire hazard and combustibles (wood, paper, oil, etc). It is also important that the location be dry, because benzyl bromide will react slowly with water to generate hydrogen bromide. Packaging materials are limited by the fact benzyl bromide is corrosive to metal (it decomposes rapidly in the presence of all common metals except nickel and leadliberating heat and hydrogen bromide). Containers of benzyl bromide may be shipped by air, rail, road, or water, and should be affixed with labels stating, "Poison and Corrosive". Regulatory requirements of the DOT should be consulted before transport. For all benzyl bromide spills, water spray may be needed to knock down vapor. Small spills of benzyl bromide should be taken up with sand or other noncombustible absorbent and placed in containers for later disposal. Large land spills should be deposited in excavated pits, ponds, or other holding areas (fitted with impermeable flexible membrane liners, if possible) for later disposal. Any surface flow should be diked with soil or sand bags, and a "universal" gelling agent applied to immobilize the spill. For water spills, trap the substance at the bottom with sand bag barriers and remove with suction hoses, or apply activated carbon and remove immobilized masses of pollutants and precipitates with mechanical dredges of lifts. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance.
운송 번호 및 가이드(DOT)1737 156
반응성 그룹Halogenated Organic Compounds
EC 분류Symbol: XiR: 36/37/38S: (2)-39
UN 분류UN Hazard Class: 6.1UN Subsidiary Risks: 8UN Pack Group: II
Reactivity AlertsPolymerizable
소화Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
응급 조치Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .
누출 비상 조치· 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.
응급 처치EYES: 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:
안전 보관Separated from strong oxidants, strong bases and food and feedstuffs. Dry. Well closed.
노출 관리 및 개인 보호· Wear positive pressure self-contained breathing apparatus (SCBA).
소화 절차Water spray, dry chemical, foam or carbon dioxide is effective. Water is effective not only for dispersing of leaked chemicals prior to its ignition, but also for cooling fire-exposed containers.If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide.Powder, water spray, foam, carbon dioxide.In case of fire: keep drums, etc., cool by spraying with water.For more Fire Fighting Procedures (Complete) data for BENZYL BROMIDE (9 total), please visit the HSDB record page.
보관 조건In general, materials which are toxic as stored or which can decomposition into toxic components due to heat, moisture, acids, or acid fumes, should be stored in cool, well ventilated place, out of sun, away from area of high fire hazard and should be periodically inspected and monitored. Incompatible materials should be isolated.... Store in dry, cool place preferably in segregated store.Separated from strong oxidants, strong bases, food and feedstuffs. Dry. Well closed.Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Light sensitive. Moisture sensitive.
정리 방법Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. ... If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters.Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Chemical protection suit including self-contained breathing apparatus.Prevent further leakage or spillage if safe to do so. Do not let product enter drains.Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations (see section 13). Keep in suitable, closed containers for disposal.Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.
비화재 누출 대응Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:
처리 방법SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Spillage Disposal: Wear eye protection, laboratory coat and nitrile rubber gloves. Depending on the size of the spill, breathing apparatus may be required. Cover the spill with a 1:1:1 mixture by weight of sodium carbonate or calcium carbonate. Clay cat litter (bentonite) and sand. When the benzyl bromide has been absorbed, scoop the mixture into a plastic container and package for disposal by burning /in incinerator equipped with air pollution control equipment/. Wash site of spillage with soap and water.Waste Disposal: Package Lots. Place in a separate, labeled container for recycling or disposal by burning. Dissolve the compound in a flammable solvent and burn in a furnace /incinerator/ equipped with an afterburner and scrubber.For more Disposal Methods (Complete) data for BENZYL BROMIDE (8 total), please visit the HSDB record page.
누출 처리Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Personal protection: chemical protection suit including self-contained breathing apparatus.
TreatmentEYES: 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.
건강 영향Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.92(2) and a regression-derived equation(3), indicates that benzyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of benzyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, due to a calculated half-life of 79 minutes for benzyl bromide(5), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in moist soil(SRC). Benzyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.45 mm Hg at 25 °C(6). Biodegradation data in soil were not available(SRC, 2014).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 340(SRC), determined from a log Kow of 2.92(2) and a regression-derived equation(3), indicates that benzyl bromide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 6.9X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5 hrs and 6 days, respectively(SRC). According to a classification scheme(67), an estimated BCF of 39(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, due to a calculated half-life of 79 minutes for benzyl bromide(7), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in water(SRC). Biodegradation data in water were not available(SRC, 2014).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl bromide, which has a vapor pressure of 0.45 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzyl bromide 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 7 days(SRC), calculated from its rate constant of 2.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Benzyl bromide in methanol at low concentration (59.4 mg/L) does not absorb light at wavelengths >290 nm but does at high concentration (297 mg/L)(4)therefore, benzyl bromide is not expected to be susceptible to direct photolysis by sunlight(SRC).
유해 작용Neurotoxin - Other CNS neurotoxin
노출 경로The substance can be absorbed into the body by inhalation and by ingestion.Oral (L626)inhalation (L626)dermal (L626)
독성 요약IDENTIFICATION AND USE: Benzyl bromide is a colorless to yellow lacrimatory liquid with a very sharp pungent tear gas odor. It is miscible in ethanol and ether, and soluble in carbon tetrachloride, benzene, and water. It is used as a chemical intermediate for foaming and frothing agents and other organic chemicals. HUMAN EXPOSURE AND TOXICITY: Liquid benzyl bromide can burn the eyesskin contact causes irritation. Inhalation causes irritation of nose and throatsevere exposure may cause pulmonary edema. It is intensely corrosive to skin, eyes, and mucous membranes. Occupational exposure to this chemical may occur through inhalation, and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicated that the general population may have been exposed to benzyl bromide by inhalation of automobile exhaust from vehicles using leaded gasoline. ANIMAL STUDIES: Benzyl bromide was inactive as a carcinogen at doses in rats. Benzyl bromide was negative for mutagenic results in Salmonella typhimurium strains TA 98 and TA 100 . This chemical was used to study chemical reactivity with 4-(p-nitrobenzyl)pyridine, and guanosine in vitro, in relation to mutagenic potency in Salmonella typhimurium and sister chromatid exchange induction in Chinese hamster cells. Benzyl bromide was found to be reactive, causing base-pair mutations in Salmonella typhimurium and also inducing sister chromatid exchange in Chinese hamster cells.Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)
Signs and SymptomsCough. Sore throat.Redness. Pain.Redness. Pain. Watering of the eyes.Burning sensation. Abdominal pain. Diarrhoea. Nausea. Vomiting.Bromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (L626, L627)
Ongoing Test StatusThe 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.[Available from, as of February 18, 2014: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=100-39-0]
Effluent ConcentrationsBenzyl bromide was identified in automotive emissions from cars burning leaded gasoline containing ethylene dibromide as a lead scavengerthe concentration detected was 1.4 ug/cu m(1).
Soil Adsorption/MobilityThe Koc of benzyl bromide is estimated as 340(SRC), using a log Kow of 2.92(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzyl bromide is expected to have moderate mobility in soil. However, adsorption on moist soil is expected to be attenuated by hydrolysis(SRC), with a calucalted chemical hydrolysis half-life of 79 minutes(4).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ ... Liquid can burn eyesskin contact causes irritation./SIGNS AND SYMPTOMS/ Inhalation causes irritation of nose and throatsevere exposure may cause pulmonary edema./SIGNS AND SYMPTOMS/ Redness, pain, Cough, sore throat, lacrimation, burning sensation, abdominal pain, diarrhea, nausea, vomiting./SIGNS AND SYMPTOMS/ Skin contact can cause severe, irritation, redness, swelling and sores. High level can cause dizziness because it attacks the nervous system.
Artificial Pollution SourcesBenzyl bromide's production and use in the manufacture of foaming and frothing agents, and in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). Its former use in leaded gasoline(2) resulted in its direct release to the environment(SRC).
수질 위해 등급(WGK)2
TSCA 등재 상태TSCA listed
RTECS 번호XS7965000
운송 번호(UN)UN 1737
독성dns-esc 1300 mmol/L ZKKOBW 92,177,78
관세 코드2903 99 80
위험 문구(R)36/37/38
위험 표시Xi
안전 문구(S)39-2
포장분류II
위험 등급6.1Eye Irrit. 2Skin Irrit. 2STOT SE 3
F 고인화성물질9-19-21
저장 분류6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터100-39-0(Hazardous Substances Data)

용도

개요

무색 내지 담황색 액체.

개요

벤질 브로마이드는 쾌적한 냄새가 나는 무색의 액체이다. 흡입 및 피부 흡수시 유독하고 물에 약간 용해되며 물 보다 밀도가 높다.

용도

최루가스에 쓰이며 금속과 세포 조직에 부식성이 있다.

용도

실험실화학, 물질의제조.

용도

Benzyl bromide is widely useful in organic synthesis as a benzyl protecting group for alcohols and carboxylic acids. It is used in the preparation of foaming and frothing agents, quaternary ammonium compounds, peniclins, photographic chemicals, synthetic resins, dyes and plasticizers and esters. It is also involved in the synthesis of (E)-(2-Iodovinyl)benzene by reacting it with diiodomethane.

일반 설명

Benzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.

제조 및 합성 방법

제조 방법

Benzyl bromide is synthesized by toluene bromination. Toluene heated to 50°C, add bromine reaction, the reaction temperature of 75-80°C, reaction 6h, fractional distillation at atmospheric pressure to remove the fraction before 140°C, and then distillation under reduced pressure, collect 112-114°C(2.0kPa) fraction, to get benzyl bromide.