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3-브로모톨루엔

3-Bromotoluene

HCID 11560
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
591-17-3
표준 SMILES
Cc1cccc(Br)c1
InChIKey
WJIFKOVZNJTSGO-UHFFFAOYSA-N
분자식
C7H7Br
평균 분자량
171.03 g/mol
단동위원소 질량
169.97311232

개요

M-bromotoluene is a clear colorless liquid. (NTP, 1992)

이름 및 식별자

우선 이름
3-Bromotoluene
IUPAC
1-bromo-3-methylbenzene
현지명
3-브로모톨루엔
영어명
3-Bromotoluene
분자식
C7H7Br
분자량
171.03

이름 및 동의어

3-BROMOTOLUENE591-17-31-Bromo-3-methylbenzenem-Bromotoluenem-Tolyl bromide3-MethylbromobenzeneBenzene, 1-bromo-3-methyl-5-Bromotoluene3-Bromo-1-methylbenzeneToluene, m-bromo-3-Methyl-1-bromobenzenem-Methylbromobenzene
이름 더 보기
3-브로모톨루엔META-BROMOTOLUENE3-BromotoL3-Bromtoluol3-Bromotolune3-bromo-toluen3-Tolylbromidem-bromo-toluen
Toluene, 3-bromo-3-methylphenyl bromideCCRIS 5981DTXSID3024659HSDB 60143-tolyl bromideEINECS 209-702-3BRN 1903633

데이터베이스 식별자

CAS
591-17-3
PubChem CID
11560
DTXSID
DTXSID3024659
ChEMBL
CHEMBL1538200
UNII
9426O61G73
EC Number
209-702-3
Nikkaji
J47.829F

물성

구조 계산 물성

XLogP
3.3
극성 표면적
0 Ų
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

실험 및 물리화학적 성질

SolventsSolvents -> Brominated Solvents
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogPlog Kow = 3.41
Density · 2건

1.41 at 68 °F (NTP, 1992) - Denser than water; will sink

1.4099 at 20 °C/4 °C

Color/FormLIQUID
Solubility · 4건

less than 1 mg/mL at 68 °F (NTP, 1992)

Sol in chloroform

Soluble in ethanol and acetone, miscible in ether

Water solubility = 51.3 mg/l

Flash Point · 2건

140 °F (NTP, 1992)

60 °C

Boiling Point · 2건

362.7 °F at 760 mmHg (NTP, 1992)

183.7 °C at 760 mm Hg

Melting Point · 2건

-40 °F (NTP, 1992)

-39.8 °C

Vapor Pressure · 3건

1 mmHg at 58.6 °F (NTP, 1992)

1.53 [mmHg]

Vapor pressure = 0.145 kPa (1.09 mm Hg) at 25 °C

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H226 (84%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

Chemical: Benzene, 1-bromo-3-methyl-

3-Bromotoluene: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelFlammable Liquid Poison
Fire HazardsThis chemical is combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound include eye and skin irritation.
Hazards Summary · 2건

Irritant; [HSDB] An irritant; Inhalation of high concentrations can cause CNS depression; [MSDSonline]

The major hazards encountered in the use and handling of 3-bromotoluene stem from its toxicologic properties. Exposure to 3-bromotoluene 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 has the potential to cause respiratory irritation and CNS depression. 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 conditions; requiring moderate heating before ignition will occur. Normal procedures may be used to fight a 3-bromotoluene fire; using water to blanket the fire. Before transporting 3-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.

화학 및 산업

용도 및 제조

Uses · 5건

Used as a solvent for fats, waxes, and resins; Also used as an intermediate and research chemical; [HSDB]

RESEARCH CHEMICAL

3-Bromotoluene is used as a solvent (for fats, waxes or resins, and as a medium for carrying out reactions) and as a chemical intermediate.

Chemical synthesis

1.53 mm Hg @ 25 °C /calculated from experimentally derived coefficients/

Methods of Manufacturing · 2건

... BY DIAZOTIZATION OF M-TOLUIDINE FOLLOWED BY TREATMENT WITH CUPROUS BROMIDE, POTASSIUM BROMIDE, & HYDROBROMIC ACID. BY HEATING A MIXT OF TOLUENE & P-BROMO-PHENOL WITH ALUMINUM TRICHLORIDE (ALCL3). BY ELIMINATION OF THE AMINO GROUP FROM 4-AMINO-3-BROMO-TOLUENE.

Replacement of hydrogen in parent compound by bromine: (a) in the presence of iron; ... Hydrogen bromide is allowed to escape, preferably being washed by incoming raw material. In some cases a method for separating isomeric compounds is necessary.

General Manufacturing InformationBenzene, 1-bromo-3-methyl-: ACTIVE
응용 분야 · 2건

용도3-Bromotoluene was used in the precise determination of bromine isotope ratio in organic compounds by MC-ICPMS ( Multicollector-Inductively Coupled Plasma Mass Spectrometer). It undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It also undergoes palladium-catalyzed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.

일반 설명3-Bromotoluene is an electron-rich aryl bromide. It participates in the Heck reaction. 3-Bromotoluene undergoes palladium-catalyzed cyanation reaction in the presence of K4[Fe(CN)6] as the cyanide surrogate. It undergoes palladium-catalysed reaction with alkynyltriarylborates to yield trisubstituted alkenylboranes.

제조 방법 · 1건

Synthesis of 3-Bromotoluene: It is derived from 3-bromo-4-aminotoluene by diazotization and reduction. The mixture of 95% ethanol, concentrated sulfuric acid and 3-bromo-4-aminotoluene was stirred and cooled to 10°C, and sodium nitrite solution was added to keep the reaction temperature not exceeding 10°C. After adding, continue stirring for 20min. Add the copper powder washed with ether, heat carefully, stop heating after the reaction starts, nitrogen will be released violently, and acetaldehyde will be formed. Then steam distillation is carried out until no oily substance evaporates. Separate the organic phase from the distillate and wash with 10% sodium hydroxide, water, concentrated sulfuric acid, and 5% sodium carbonate solution in sequence. Dry with anhydrous calcium chloride, filter, distill, collect 180-183 ℃ (99.75kPa) fractions to obtain colorless pure 3-bromotoluene with a yield of over 50%.

관련 반응

179건
반응 기록 만들기
HRID 80080 반응식
HRID 80080반응물로uspto-grants-2014_09
HRID 91021 반응식
HRID 91021반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 94438 반응식
HRID 94438반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 119167 반응식
HRID 119167반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 121620 반응식
HRID 121620반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 123047 반응식
HRID 123047반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 126862 반응식
HRID 126862반응물로uspto-grants-1981_03
HRID 157752 반응식
HRID 157752반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
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화합물 노트

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Refractive IndexIndex of refraction: 1.5510 at 20 °C/D
Heat of Vaporization10,537.1 gcal/gmole

물리화학적 성질

녹는점
-40 °C · -40 °C
끓는 점
183.7 °C · 183.7 °C(lit.)
밀도
1.41 g/mL · 1.41 g/mL at 25 °C(lit.)
증기압
2.04 hPa · 2.04 hPa ( 25 °C)
굴절률
20 · n20/D 1.552(lit.)
인화점
140 °F · 140 °F
저장 조건
30 °C · Store below +30°C.
용해도
0.05 g/L · 0.05g/L
물리적 상태
액체
Specific Gravity
1.41 · 1.410
색상
무색투명~연황색
수용성
불용성
Merck
14 · 14,1439
BRN
1903633 · 1903633
Henry's Law Constant
1.5 · 1.5×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Dielectric constant
5.36 · 5.3600000000000003
InChI
1S/C7H7Br/c1-6-3-2-4-7(8)5-6/h2-5H,1H3
InChIKey
WJIFKOVZNJTSGO-UHFFFAOYSA-N
SMILES
Cc1cccc(Br)c1
NIST
1 · Benzene, 1-bromo-3-methyl-(591-17-3)
EPA
m-Bromotoluene (591-17-3)

화학적 성질

colorless to light yellow liquid. Insoluble in water, soluble in ethanol and ether.

Reactive GroupAryl Halides
Reactivity AlertsHighly Flammable
Reactivity ProfileM-BROMOTOLUENE is incompatible with strong oxidizing agents. (NTP, 1992)
Air and Water ReactionsHighly flammable. Insoluble in water.
Hazard Classes and CategoriesFlam. Liq. 3 (84%)
Skin, Eye, and Respiratory IrritationsIrritant

안전 및 보호

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1건

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.

Nonfire Spill Response · 1건

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.

Disposal Methods · 1건

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 · 1건

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 EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Personal Protective Equipment (PPE) · 1건

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)

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 434(SRC), derived from a molecular structure estimation method(2), suggests that 3-bromotoluene will have moderate mobility in soil(SRC). Its high Henry's Law constant, 6.71X10-3 atm-cu m/mole(SRC), estimated from its water solubility(3), high vapor pressure, 1.53 mm Hg at 25 °C(5), and moderate adsorptivity to soil suggests that volatilization may be an important fate process from both moist and dry soil surfaces(4,SRC). Experimental data suggests that 3-bromotoluene may be subject to direct photolysis on the soil surface(6). 3-Bromotoluene's potential for biodegradation in soil is unknown(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 430(SRC) determined from molecular structure(2), indicates that 3-bromotoluene may adsorb to sediment and particulate matter in the water column(SRC). It is expected to readily volatilize from water based on its Henry's Law constant of 6.7X10-3 atm-cu m/mole(SRC), estimated from its water solubility(3) and vapor pressure(7). Estimated half-lives for a model river and model lake are 4.0 hours and 5.2 days, respectively(4,SRC). Using a model which takes adsorption into account(7), the volatilization half-life of 3-bromotoluene in an environmental pond is estimated to be 14.9 days. According to a recommended classification scheme(6), an estimated BCF value of 230(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), 3-bromotoluene, which has a vapor pressure of 1.53 mm Hg at 25 °C(2) will exist as a vapor in the ambient atmosphere(SRC). Vapor-phase 3-bromotoluene degrades in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction is estimated to be 4.8 days(3,SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1건

Using an estimation method based on molecular connectivity indices(1), the Koc for 3-bromotoluene is estimated to be 430(SRC). According to a suggested classification scheme(2), this Koc value suggests that 3-bromotoluene will have medium mobility in soil(SRC).

Artificial Pollution Sources3-Bromotoluene's production and use as a solvent(1) and chemical intermediate(2) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1건

A BCF of 230 was estimated for 3-bromotoluene(SRC), using its log Kow of 3.41(1,SRC), and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that 3-bromotoluene has a moderately high potential for bioconcentration in fish and aquatic organisms(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant of 3-bromotoluene calculated from its vapor pressure, 1.53 mm Hg at 25 °C(3), and water solubility, 513 mg/l(1), is 6.7X10-3 atm-cu m/mole(SRC), which indicates that volatilization from environmental waters is probably significant, and may be rapid(2). The volatilization half-life of 3-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) is estimated to be 4.0 hr and 5.2 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 3-bromotoluene in an environmental pond which considers adsorption is estimated to be 14.9 days(4,SRC).

Non-Human Toxicity Excerpts · 2건

RESPIRATORY IRRITATION &, IN HIGH CONCN ... /CNS DEPRESSION/ IN EXPTL ANIMALS.

m-Bromotoluene tested negative for mutagenicity in Salmonella assays.

Environmental Abiotic Degradation · 1건

The rate constant for the vapor-phase reaction of 3-bromotoluene with photochemically-produced hydroxyl radicals is estimated to be 3.34X10-12 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 is estimated to be 4.8 days(1,SRC). 3-Bromotoluene does not contain any functional groups that are susceptible to hydrolysis(2); therefore, hydrolysis is not expected to be significant in natural waters(SRC). Irradiation of 3-bromotoluene (in hexane solution) with artificial UV light above 290 nm resulted in a dehalogenation of 0.36% over a two hour period(3).

Probable Routes of Human ExposureOccupational exposure may occur through inhalation or dermal contact at sites where 3-bromotoluene is manufactured, used as a solvent, or used as chemical intermediate. (SRC)
Environmental Fate/Exposure Summary · 1건

3-Bromotoluene may be released to the environment through evaporation from solvent uses or in waste streams generated at sites of production and use. If released to the atmosphere, 3-bromotoluene is expected to degrade by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction is estimated to be 4.8 days. If released to water, 3-bromotoluene may be removed from the water column by volatilization and adsorption. Using an estimated Henry's Law constant of 6.7X10-3 atm-cu m/mol, volatilization half-lives of 4.1 hr and 5.2 days are estimated for a model river and model lake, respectively. The effect of adsorption to sediment is considered in the estimated volatilization half-life of 14.9 days from an environmental pond, but not from the model river or model lake. An estimated Koc value of 430 suggests that if 3-bromotoluene is released to soil, moderate leaching may occur. Based on its estimated Henry's Law constant and measured vapor pressure (1.53 mm 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. Ot's estimated BCF of 230 suggests that there is a moderately high potential for bioconcentration in aquatic organisms. Occupational exposure may occur through inhalation or dermal contact at sites where 3-bromotoluene is manufactured, used as a solvent or used as a chemical intermediate. (SRC)

Toxicity DataLC50 (rat) = 6800 mg/m3

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XS7965400
ridadr
UN 1993 3/PG 3
HS 번호
29036990
risk_code
22-36/37/38
hazard_code
Xn,Xi
safety_code
26-36-37/39
위험 등급
3
기존화학 물질
2004-3-2925
F 고인화성물질
8
위험 참고 사항
Harmful/Irritant
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
591-17-3(Hazardous Substances Data)

상·하류 제품 정보

상류 원료

2-Bromo-4-methylaniline구리에틸알코올

하류 제품

TERT-부틸4-(3-FORMYLBENZYL)TETRAHYDRO-1(2H)-PYRAZINECARBOXYLATE3-Bromobenzoic acid트리 -m- 톨릴 포스 핀3-(에틸(메틸)카바모일)페닐붕소산3-(Dimethylcarbamoyl)phenylboronic acid3-Ethynyltoluene5-Bromo-2-chlorotoluene2,5-Dibromotoluene3-메틸페네틸브로마이드브로모벤젠3-브로모밴즈알데히드1-(브로모메틸)-3-페녹시벤젠3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)toluene2-브로모-4-메틸벤즈알데히드3-Phenyltoluene3-Methylbenzotrifluoride