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알파-브로모-메타-크실렌

m-Xylyl bromide

HCID 12099
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
620-13-3
표준 SMILES
Cc1cccc(CBr)c1
InChIKey
FWLWTILKTABGKQ-UHFFFAOYSA-N
분자식
C8H9Br
평균 분자량
185.06 g/mol
단동위원소 질량
183.98876239

개요

m-Xylyl bromide, also known as methylbenzyl bromide or T-stoff, is a poisonous organic chemical compound, formerly used as a tear gas. Physically it is a colourless liquid (melting point 21 °C) with a pleasant aromatic odour. m-Xylyl bromide is highly toxic, irritant and lachrymatory, and has been incorporated in chemical weapons since the early months of World War I. The first extensive use of xylyl bromide was the firing by German forces of 18,000 "T-shells" at Russian positions in the Battle of Bolimów in January 1915. In the absence of clarification, the name "xylyl bromide" may refer to any one of 3 xylyl isomers (o-Xylyl, p-Xylyl, m-Xylyl) or a mixture of all three.

이름 및 식별자

우선 이름
m-Xylyl bromide
IUPAC
1-(bromomethyl)-3-methylbenzene
현지명
알파-브로모-메타-크실렌
영어명
3-Methylbenzyl bromide
분자식
C8H9Br
분자량
185.06

이름 및 동의어

3-Methylbenzyl bromide1-(Bromomethyl)-3-methylbenzenealpha-Bromo-m-xyleneM-XYLYL BROMIDEBenzene, 1-(bromomethyl)-3-methyl-.alpha.-Bromo-m-xylenea-bromo-m-xylene3-bromomethyltolueneHSDB 2191EINECS 210-625-2UNII-U49150ER3LAI3-20884
이름 더 보기
메타-자일릴브로마이드알파-브로모-메타-크실렌메타-실릴브로마이드메타-자일릴 브로마이드bromo-xyleneà-bromo-m-xyleneα-bromo-m-xylene?-bromo-m-xylenealpha-bromo-m-xylen
U49150ER3LNSC-60146M-XYLYL BROMIDE [MI]DTXSID1060716FWLWTILKTABGKQ-UHFFFAOYSA-alphaBromomxylenemXylene, alphabromomMethylbenzyl bromide

데이터베이스 식별자

CAS
620-13-3
PubChem CID
12099
DTXSID
DTXSID1060716

물성

구조 계산 물성보충 중

XLogP
3
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
1
무거운 원자 수
9
형식 전하
0
복잡도
80.6

실험 및 물리화학적 성질

Chemical ClassesOther Classes -> Halogenated Monoaromatics
SpringerMaterials PropertiesOptical coefficient
Density1.3711 g/cu cm at 23 °C
Color/FormLiquid
Solubility · 4건

Insoluble in water

Practically insoluble in water

Soluble in organic solvents

Very soluble in ethanol and ethyl ether

Flash Point82 °C (180 °F) - closed cup
Boiling Point · 2건

212.5 °C

BP: 212-215 °C with slight decomposition

DecompositionHazardous decomposition products formed under fire conditions. - Carbon oxides, Hydrogen bromide gas
Vapor Pressure0.19 [mmHg]
Refractive IndexIndex of refraction: 1.5660 at 20 °C/D
Physical Description

안전 및 규제

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

GHS 분류

GHS Classification · 4건

Danger

H302 (87.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Regulatory Information · 2건

Chemical: Benzene, 1-(bromomethyl)-3-methyl-

Benzene, 1-(bromomethyl)-3-methyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Fire Potential · 2건

Combustile

Moderate, when exposed to heat or flame.

Hazards SummaryPowerful lachrymator; [Merck Index] Toxic by inhalation and ingestion; Strong irritant; [Hawley] Causes burns; Toxic by inhalation; Inhalation can cause chemical pneumonitis; [MSDSonline]
Toxic Combustion ProductsHazardous decomposition products formed under fire conditions. - Carbon oxides, Hydrogen bromide gas
Hazard Classes and CategoriesAcute Tox. 4 (87.2%)
Shipment Methods and Regulations · 3건

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)./

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

용도 및 제조

Uses · 6건

Used in organic synthesis and as a military tear gas; [Merck Index]

Organic synthesis, tear gas. /Mixture of ortho-, meta-, and para-isomers/

In war gas formulations.

Intermediate

A poison. /Xylyl Bromide/

Occupational exposure to xylyl bromide may occur through inhalation and dermal contact with this compound at workplaces where xylyl bromide is produced or used.

Methods of ManufacturingBromination of xylene. /Mixture of ortho-, meta-, and para-isomers/
Formulations/PreparationsGrade: Technical. /Mixture of ortho-, meta-, and para-isomers/
General Manufacturing InformationBenzene, 1-(bromomethyl)-3-methyl-: INACTIVE

상·하류 제품 정보

상류 원료

3-메틸-1-디브로모메틸벤젠6-Oxatricyclo[3.2.1.02,7]octan-8-oneCobalt, bis[[2,3-butanedione di(oximato-κN)](1-)][(3-methylphenyl)methyl](pyridine)-, (OC-6-12)- (9CI)

관련 반응

102건
반응 기록 만들기
HRID 51327 반응식
HRID 51327반응물로uspto-grants-2004_03
HRID 51403 반응식
HRID 51403반응물로uspto-grants-2004_03
HRID 124918 반응식
HRID 124918반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 125526 반응식
HRID 125526반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 226938 반응식
HRID 226938반응물로uspto-grants-2009_07
HRID 226942 반응식
HRID 226942반응물로uspto-grants-2009_07
HRID 226947 반응식
HRID 226947반응물로uspto-grants-2009_07
HRID 226948 반응식
HRID 226948반응물로uspto-grants-2009_07
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화합물 노트

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더보기
새 노트새 반응견적 요청하기
UNII
U49150ER3L
EC Number
210-625-2
Nikkaji
J7.046G
Liquid; [Merck Index]
Stability/Shelf LifeStable under recommended storage conditions.

물리화학적 성질

녹는점
-20.49 °C · -20.49°C (estimate)
끓는 점
185 °C340 · 185 °C340 mm Hg(lit.)
밀도
1.37 g/mL · 1.37 g/mL at 25 °C(lit.)
굴절률
20 · n20/D 1.566(lit.)
인화점
180 °F · 180 °F
저장 조건
2 · under inert gas (nitrogen or Argon) at 2-8°C
용해도
클로로포름(소량으로 용해), 메탄올(약간 용해됨)
물리적 상태
액체
색상
무색투명~연황색
수용성
실질적으로 불용성
Merck
14 · 14,10090
BRN
2076425 · 2076425
Henry's Law Constant
1.3 · 1.3×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C8H9Br/c1-7-3-2-4-8(5-7)6-9/h2-5H,6H2,1H3
InChIKey
FWLWTILKTABGKQ-UHFFFAOYSA-N
SMILES
Cc1cccc(CBr)c1
NIST
1 · 1-Bromomethyl-3-methylbenzene(620-13-3)
EPA
1 · Benzene, 1-(bromomethyl)-3-methyl- (620-13-3)

화학적 성질

clear colorless to light yellow liquid

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

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.

Shipping Name/ Number DOT/UN/NA/IMO · 3건

UN 1701; Xylyl bromide, liquid

UN 3417; Xylyl bromide, solid

IMO 6.1; Xylyl bromide, liquid; Xylyl bromide, solid

Skin, Eye, and Respiratory IrritationsStrong irritant to eyes and skin.
Hazardous Reactivities and IncompatibilitiesAlcohols, Bases, Amines, Oxidizing agents

안전 및 보호

Fire Fighting Procedures · 4건

Wear self contained breathing apparatus for fire fighting if necessary.

For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray; solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.

If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Use water spray to knock-down vapors. /Xylyl bromide, liquid; Xylyl bromide, solid/

Personnel protection: ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Xylyl bromide, liquid; Xylyl bromide, solid/

Cleanup Methods · 3건

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.

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. Keep in suitable, closed containers for disposal.

Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

Disposal Methods · 2건

SRP: 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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.

Preventive Measures · 5건

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the buildup of electrostatic charge.

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. Use water spray to knock-down vapors. /Xylyl bromide, liquid; Xylyl bromide, solid/

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... 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. ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Xylyl bromide, liquid; Xylyl bromide, solid/

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Personal Protective Equipment (PPE) · 5건

Hand protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Skin and body protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Eye protection: Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Personnel protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective gloves, boots, and googles. /Xylyl bromide, liquid; Xylyl bromide, solid/

독성 정보

Treatment · 1건

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.

Health EffectsStrong lachrymator. Strong irritant to eyes, skin and soft tissues. Highly toxic if inhaled, swallowed or absorbed through skin.
Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 710(SRC), determined from a structure estimation method(2), indicates that m-xylyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of m-xylyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). m-xylyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). However, based on hydrolysis half-lives of 3.4 hours and 4.3 minutes for the o- and p-isomers, respectively(4), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in moist soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 710(SRC), determined from a structure estimation method(2), indicates that m-xylyl bromide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 7.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hrs and 6 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 85(SRC), from an estimated log Kow of 3.43(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, based on hydrolysis half-lives of 3.4 hours and 4.3 minutes for the o- and p-isomers, respectively(6), adsorption, volatilization, bioconcentration, and biodegradation are not expected to be important environmental fate processes in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), m-xylyl bromide, which has an estimated vapor pressure of 0.15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase m-xylyl 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 4.3 days(SRC), calculated from its rate constant of 3.7X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). m-Xylyl bromide does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1건

Organobromide compounds such as m-Xylyl bromide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines) and methionine residues of the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs.

Signs and SymptomsCauses severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to coma, nausea, vomiting, and metabolic acidosis may occur.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of m-xylyl bromide can be estimated to be 710(SRC). According to a classification scheme(2), this estimated Koc value suggests that m-xylyl bromide is expected to have moderate mobility in soil. However, based on hydrolysis half-lives of 3.4 hours and 4.3 minutes for the o- and p-isomers, respectively(3), adsorption is not likely to be important due to rapid hydrolysis of m-xylyl bromide(SRC).

Human Toxicity Excerpts · 3건

/OTHER TOXICITY INFORMATION/ Toxic by inhalation and ingestion.

/OTHER TOXICITY INFORMATION/ Powerful lacrimator.

/OTHER TOXICITY INFORMATION/... Strongly lacrimatory. /Xylyl bromides/

Artificial Pollution Sources · 1건

m-Xylyl bromide's production and presense in a in mixture with the o- and p-isomers in organic synthesis(1) may result in its release to the environment through various waste streams. Its use in mixture with o- and p-isomers as a tear gas will result in its direct release to the environment(SRC).

Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)
Environmental Bioconcentration · 1건

An estimated BCF of 85 was calculated in fish for m-xylyl bromide(SRC), using an estimated log Kow of 3.43(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). However, based on hydrolysis half-lives of 3.4 hours and 4.3 minutes for the o- and p-isomers, respectively(3), bioconcentration is not likely to be important due to rapid hydrolysis of m-xylyl bromide(SRC).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
CY9039200
ridadr
UN 1701 6.1/PG 2
HS 번호
29039990
risk_code
20/22-34-20/21/22
hazard_code
C
safety_code
26-27-36/37/39-45-7/9
포장분류
II
위험 등급
6.1
위험 참고 사항
Corrosive
Hazard Classifications
Acute Tox. 4 OralSkin Corr. 1B
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
620-13-3(Hazardous Substances Data)
1,3-Bis(bromomethyl)benzene
1-브로모-2-(브로모메틸)-4-메틸벤젠
브로모트리클로로메탄
메틸(3-벤질)알코올
테트라브로모메테인
p-자일렌
3-메틸벤즈알데하이드
3-자일렌

하류 제품

m-Tolyl-methanesulfonyl chloride4-브로모-메타-크실렌Methyl 3-methylphenylacetate4,4,5,5-tetramethyl-2-(4-((3-methylbenzyl)oxy)phenyl)-1,3,2-dioxaborolane