브로모아세톤

Bromoacetone

HCID 11715CAS 598-31-2

기본 정보

표준 SMILES
CC(=O)CBr
InChIKey
VQFAIAKCILWQPZ-UHFFFAOYSA-N
분자식
C3H5BrO
평균 분자량
136.98 g/mol
단동위원소 질량
135.95237688

개요

Bromoacetone appears as a clear colorless liquid turning violet on standing, even in the absence of air, and decomposing to a black resinous mass on long standing. Denser than water and poorly soluble in water. Hence sinks in water. A violent lachrymator--low concentrations are very irritating to the eyes; high concentrations or prolonged exposure at lower concentrations may have adverse health effects. Very toxic by inhalation. Contact with the liquid causes painful burns. Used as a chemical war gas.

이름 및 식별자

우선 이름
Bromoacetone
IUPAC
1-bromopropan-2-one
현지명
브로모아세톤
영어명
Bromoacetone
분자식
C3H5BrO
분자량
136.98

이름 및 동의어

BROMOACETONE598-31-21-Bromo-2-propanone1-bromopropan-2-oneMonobromoacetone1-BromoacetoneAcetonyl bromideMartonite2-Propanone, 1-bromo-Bromo-2-propanoneBromomethyl methyl ketoneB-Stoff
이름 더 보기
브로모아세톤아세토닐브롬화물브로모-2-프로판온1-브로모-2-프로판온1-브로모프로판-2-온2-프로판온, 1-브로모-마토나이트모노브로모아세톤브로모-2-프로파논브로모메틸메틸케톤아세톤, 브로모-아세톤일 브로마이드아세틸메틸브롬화물알파-브로모아세톤CH3COCH2BrBromopropanoneacetonylbromidebromo-2-propanon
Acetylmethyl bromideAcetyl methyl bromide2-Propanone, bromo-alpha-BromoacetoneBA (tear gas)3O8L0EWR5QDTXSID6060507CHEBI:51845

데이터베이스 식별자

CAS
598-31-2
PubChem CID
11715
DTXSID
DTXSID6060507
ChEMBL
CHEMBL1085947
ChEBI
CHEBI:51845
UNII
3O8L0EWR5Q
EC Number
209-928-2
Nikkaji
J3.305G

물성

구조 계산 물성

XLogP
0.7
극성 표면적
17.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
1
무거운 원자 수
5

실험 및 물리화학적 성질

Chemical Classes · 2건

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Flammable agents - 2nd degree

SpringerMaterials PropertiesOptical coefficient
LogP0.11
OdorPUNGENT ODOR
Density · 4건

1.634 at 73.4 °F (USCG, 1999) - Denser than water; will sink

1.634 g/cu cm at 23 °C

Relative density (water = 1): 1.63

1.634 @ 23°C

Color/FormColorless liquid; rapidly becomes violet even in absence of air

물리화학적 성질

녹는점
-36 · -36,5°C
끓는 점
137 °C · 137°C
밀도
1 · 1,63 g/cm3
굴절률
15 · nD15 1.4697
인화점
51 ℃ · 51℃
Specific Gravity
1.63 · 1.63 (0℃)

화학적 성질

Colorless liquid when pure, rapidly becomes violet even in absence of air. Soluble in ace- tone, alcohol, benzene, and ether; slightly soluble in water.

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P271, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P320, P321, 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 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 2건

Chemical: 2-Propanone, 1-bromo-

The 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.)

DOT LabelPoison Inhalation Hazard Flammable Liquid
Fire Hazards · 3건

Special Hazards of Combustion Products: Toxic fumes of Bromine (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialFlammable
Health Hazards · 2건

Very powerful lachrymator and upper respiratory tract irritant. Intensely irritating to the eyes, nose, throat, and lungs. Corrosive to the skin. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Use water spray, powder.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2건

· 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.

First Aid · 2건

Call a physician.

General First Aid:

Safe StorageSeparated from strong oxidants and food and feedstuffs. Well closed. Keep in a well-ventilated room.
Exposure Control and Personal Protection · 2건

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

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 Effects · 1건

A strong lachrymator. Inhalation, ingestion or skin contact with material may cause severe injury or death. Animal studies indicate that at very high concentrations it can cause kidney and liver damage. Bromoacetone causes ocular irritation in 30% of human subjects at 0.1 ppm and 100% of human subjects at 1.0 ppm.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that bromoacetone is expected to have very high mobility in soil(SRC). Volatilization of bromoacetone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Bromoacetone is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9 mm Hg at 20 °C(4). Photolysis may occur on soil surfaces exposed to sunlight(5). Biodegradation data in soil were not available(SRC, 2010).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5(SRC), determined from a structure estimation method(2), indicates that bromoacetone is not 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 5.7X10-6 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 4 and 31 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.11(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Photolysis may be an important degradation process for bromoacetone in sunlit water(8). If bromoacetone is spilled into a body of water, it will sink to the bottom of the water column, dissolve slowly and turn violet rapidly(9). Although ketones are generally resistant to hydrolysis, the substituted bromine group may be susceptible to hydrolysis(3). Biodegradation data in water were not available(SRC, 2010).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bromoacetone, which has a vapor pressure of 9 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase bromoacetone 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 54 days(SRC), calculated from its rate constant of 3.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Bromoacetone absorbs light strongly in the wavelength region between 290-350 nm, with a UV max occurring at 300 nm(4); however, kinetic rate data are not available to predict the rate at which direct photolysis may occur in the environment(5). Bromoacetone turns violet rapidly in the presence of light, even in the absence of air(6).

Adverse EffectsDermatotoxin - Skin burns.
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation of its vapour and by ingestion.

Oral (L626) ; inhalation (L626) ; dermal (L626)

Toxicity Summary · 1건

Organobromide compounds such as bromoacetone 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.

규제 정보

RCRA Requirements · 1건

P017; As stipulated in 40 CFR 261.33, when bromoacetone, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

TSCA Requirements · 1건

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. 2-Propanone, 1-bromo is included on this list.

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

안전 데이터

ridadr
UN 1569
HS 번호
29147000
risk_code
11-23/24/25-34
safety_code
26-36/37/39
포장분류
II
위험 등급
6.1

화학 및 산업

약리 정보

Metabolism/Metabolites · 2건

... In this study, the factors influencing the disposition and biotransformation of 1-bromopropane (1-BrP) were examined in male F344 rats and B6C3F1 mice following inhalation exposure (800 ppm) or intravenous administration (5, 20, and 100 mg/kg). (1,2,3-13C)1-BrP and (1-14C)1-BrP were administered to enable characterization of urinary metabolites using NMR spectroscopy, LC-MS/MS, and HPLC coupled radiochromatography. ... The molar ratio of exhaled 14CO2 to total released bromide, which decreased as dose increased, demonstrated that the proportion of 1-BrP metabolized via oxidation relative to pathways dependent on glutathione conjugation is inversely proportional to dose in the rat. (14C)1-BrP equivalents were recovered in urine (13-17%, rats; 14-23% mice), feces (< 2%), or retained in the tissues and carcass (< 6%) of rats and mice administered iv 5 to 100 mg/kg (14C)1-BrP. Metabolites characterized in urine of rats and mice include N-acetyl-S-propylcysteine, N-acetyl-3-(propylsulfinyl)alanine, N-acetyl-S-(2-hydroxypropyl)cysteine, 1-bromo-2-hydroxypropane-O-glucuronide, N-acetyl-S-(2-oxopropyl)cysteine, and N-acetyl-3-[(2-oxopropyl)sulfinyl]alanine. These metabolites may be formed following oxidation of 1-bromopropane to 1-bromo-2-propanol and bromoacetone and following subsequent glutathione conjugation with either of these compounds ...

Bromoacetone is a metabolic byproduct of bromopropane. It can react with glutathione and generate conjugates that are subsequently secreted in the urine.

용도 및 제조

Uses · 4건

Was used as a chemical war gas; [CAMEO]

Chemical war gas /former use/

Organic synthesis; tear gas /Former use/

Bromoacetone is an industrial and laboratory chemical. Occupational exposure to bromoacetone may occur through inhalation and dermal contact with this compound at workplaces where bromoacetone is produced or used.

Methods of Manufacturing · 2건

Preparation by bromination of acetone.

By treating aq acetone with bromine and sodium chlorate at 30-40 °C

Formulations/PreparationsGrades: technical
General Manufacturing Information · 1건

Bromo organic compounds may be formed during water chlorination treatments by the oxidation of naturally occurring bromine via hypochlorous acid to hypobromous acid, which is then capable of forming organic bromine compounds; however, this scenario has never been experimentally shown to produce bromoacetone.

응용 분야 · 2건

용도Chemical war gas.

일반 설명A clear colorless liquid turning violet on standing, even in the absence of air, and decomposing to a black resinous mass on long standing. Denser than water and poorly soluble in water. Hence sinks in water. A violent lachrymator--low concentrations are very irritating to the eyes; high concentrations or prolonged exposure at lower concentrations may have adverse health effects. Very toxic by inhalation. Contact with the liquid causes painful burns. Used as a chemical war gas.

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]

추가 설명

정의ChEBI: An alpha-bromoketone that is acetone in which one of the hydrogens is replaced by a bromine atom. A poweful lachrymator, it was formerly used as a chemical weapon.

관련 반응

109건

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