Ethyl Bromide

HCID 6332CAS 74-96-4

基本情報

標準SMILES
CCBr
InChIKey
RDHPKYGYEGBMSE-UHFFFAOYSA-N
分子式
C2H5Br
平均分子量
108.97 g/mol
単同位体質量
107.95746226

概要

Bromoethane can cause cancer according to The National Toxicology Program.

名称と識別子

優先名称
Ethyl Bromide
IUPAC
bromoethane
現地名
ブロモエタン
英語名
Bromoethane
分子式
C2H5Br
分子量
108.96

名称と別名

Bromoethane74-96-4ETHYL BROMIDE1-BromoethaneEthane, bromo-Bromic etherMonobromoethaneHydrobromic etherBromure d'ethyleEtylu bromekHalon 2001NCI-C55481
名称をさらに表示
ブロモエタンブロムエーテルハロン-2001臭化エチルエチルブロミド1-ブロモエタンエチル ブロマイドエチルブロマイド臭化エチル(ブロモエタン)ブロモエタン エチルブロミド臭化エチル( ブロモエタン)ブロモエタン,臭化エチルC2H5BrBromethanEthylbromid1-BromethanF160B1SINOBIOhalon2001Bromoethan
DTXSID6020199NCI-554813LI8384T9PHNSC-8824DTXCID60199CHEBI:47232BromoethanumRefChem:5617

データベース識別子

CAS
74-96-4
PubChem CID
6332
DTXSID
DTXSID6020199
ChEMBL
CHEMBL156378
ChEBI
CHEBI:47232
UNII
LI8384T9PH
EC Number
200-825-8
Nikkaji
J2.383C

物性

構造計算による物性

XLogP
1.4
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
3

実験および物理化学的性質

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesCoriolis coupling
LogP · 2 件

log Kow = 1.61

1.61

Odor · 2 件

... Ether-like odor

Ethereal odor

TasteBurning taste

物理化学的性質

融点
-119 °C · -119 °C
沸点
37 · 37-40 °C(lit.)
比重(密度)
1.46 g/mL · 1.46 g/mL at 25 °C(lit.)
蒸気密度
3.75 · ~3.75 (vs air)
蒸気圧
25.32 psi · 25.32 psi ( 55 °C)
屈折率
20 · n20/D 1.425(lit.)
化学的性質 · 1 件

化学的特性Bromoethane is a colorless, volatile, flammable liquid. When exposed to air and light, it turns yellow. It has an ethereal odor and somewhat burning taste. Bromoethane has a specific gravity of 1.4505 between 4° and 25°C, a boiling point of 38.4°C, a melting point of -119°C, and a vapor pressure of 475 mm mercury at 25°C. It is 0.91% (w/w) soluble in water at 20°C and is miscible with ethanol, ethyl ether, chloroform, and other organic solvents. It has a flash point of -20°C (closed cup). The autoignition temperature is 511°C. The flammable limits in air are between 6.7570 and 11.25%. Although bromoethane is relatively stable, when heated to decomposition it emits highly toxic fumes of bromine and hydrobromide; it can react with oxidizing materials (ITII, 1979; Sittig, 1979; Torkelson and Rowe, 1981; Merck, 1983; Sax, 1984).

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

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

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P318, P330, P370+P378, P403+P235, P405, P501, and P502 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Ethane, bromo-

Hazard Traits - Carcinogenicity

Ethane, bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, bromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 17-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11503

Bromoethane: HSNO Approval: HSR002987 Approved with controls

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.)

Other Safety InformationIMAP assessments - Ethane, bromo-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 3 件

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

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

Extremely flammable.

Fire PotentialDangerously flammable by heat, open flame (sparks), oxidizers.
Health Hazards · 2 件

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

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

安全と保護具

Fire Fighting · 2 件

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

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

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

Refer for medical attention .

Accidental Release Measures · 2 件

· 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 · 3 件

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.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from incompatible materials. Cool. Dry. Well closed. Ventilation along the floor.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

Body Burden · 1 件

Clinical cases of occupational ethyl bromide intoxication observed between 1937 and 1942 /were reviewed/. ...Blood bromine concentration of patients suffering from ethyl bromide poisoning at the time of admission were reported to be 15-53 mg/100 mL. Spinal fluid bromine concentrations were 4-7 mg/100 mL. After 5-10 days without exposure, the patients' blood bromine levels were 5-7 mg/100 mL; however after 2-3 weeks, these returned to background levels of 0.61-1.81 mg/100 mL. No background levels for spinal fluid bromine concentration are reported. ...

Treatment · 1 件

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.

Interactions · 1 件

There is a possible interaction of epinephrine with ethyl bromide. In studies with dogs, ethyl bromide and other halogenated compounds have been shown to cause cardiac syncope. Anesthetized dogs that had inhaled ethyl bromide and that were subsequently injected with 0.03 mg/kg epinephrine died of ventricular fibrillation.

Target OrgansEyes, skin, respiratory system, liver, kidneys, cardiovascular system, central nervous system
Health EffectsBromoethane is a weak carcinogen and a strong lachrymator. Studies in rodents indicated that chronic exposure to moderately high levels of bromoethane can lead to marginal increases in lung, adrenal and brain neoplasms (A3149)
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that ethyl bromide is expected to have very high mobility in soil(SRC). Volatilization of ethyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.4X10-3 atm-cu m/mole(SRC) based upon its vapor pressure, 467 mm Hg(3), and water solubility, 9,000 mg/L(4). Hydrolysis in moist soil may be an important environmental fate process(SRC) based upon aqueous hydrolysis half-lives of 40 and 30 days at pH 7 and at 20 and 25 °C, respectively(5,6). Ethyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Utilizing the Japanese MITI test, 33% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is not likely to be a fast environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that ethyl bromide 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 7.4X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 467 mm Hg(4), and water solubility, 9,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 5(SRC), from its log Kow of 1.61(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis half-lives of 40 and 30 days at pH 7 and at 20 and 25 °C(8,9), respectively, indicate that hydrolysis is an important enviornmental fate process in water(SRC). Utilizing the Japanese MITI test, 33% of the Theoretical BOD was reached in 4 weeks(10) indicating that biodegradation is not likely to be a fast environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl bromide, which has a vapor pressure of 467 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl 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 45 days(SRC), calculated from its rate constant of 3.5X10-13 cu cm/molecule-sec at 25 °C(3). Ethyl bromide does not contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

法規制情報

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 3/11/94; Reporting date: 5/10/94.

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. Ethyl bromide is included on this list. Effective date: 3/11/94; Sunset date: 6/30/98.

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethyl bromide is produced, as an intermediate or a final product, by process units covered under this subpart.

State Drinking Water Guidelines(WA) WASHINGTON 5 ug/L

安全データ

F
8
wgk
1
IDLA
2,000 ppm
tsca
TSCA listed
rtecs
KH6475000
ridadr
UN 1891

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

... It may be hydrolyzed to a significant degree in body, resulting in formation of inorganic bromides.

Ethylmercapturic acid is also an ethyl bromide metabolite as shown by its appearance in the urine of rats administered 1.25 g/kg subcutaneous doses of ethyl bromide. This finding was supported by the presence of S-ethyl-cysteine in acid-treated urine.

Ethyl bromide is a substrate for glutathione S-transferase. Female Wistar rats given 1.16 millimoles of ethyl bromide in oil by gavage were sacrificed 2 hours later, and livers were assayed for glutathione; ethyl bromide-treated rats showed liver glutathione levels 52% that of controls.

The substrate specificity of ammonia monooxygenase in whole cells of the nitrifying bacterium Nitrosomonas europaea have been determined for a number of aliphatic halogenated hydrocarbons. The effect of the halogen substituent and carbon chain length on substrate reactivity was studied by measuring the rates of oxidation of monohalogenated ethanes (fluoroethane, chloroethane, bromoethane, and iodoethane) by whole cells of Nitrosomonas europaea. For monohalogenated ethanes, acetaldehyde was the major organic product and little or none of any of the alternate predicted products (2-halogenated alcohols) were detected.

For more Metabolism/Metabolites (Complete) data for Ethyl bromide (7 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 4 件

Absorption and excretion through the lungs is rapid ... .

Ethyl bromide has been shown to be absorbed through intact rabbit skin. Ethyl bromide was detected in the rabbits' exhaled air after 20 minutes of skin contact.

Ethyl bromide administered intraperitoneally to rats and mice was found to be rapidly detoxified and did not accumulate upon repeated administration.

Unchanged bromoethane account for approximately 70% of the dose in the expired air of rats dosed orally by gavage.

用途と製造

Uses · 5 件

Used in organic synthesis and as a solvent for chemicals and pharmaceuticals; Used in the past as a refrigerant and an anesthetic; [ACGIH]

Ethylating agent in organic synthesis; as refrigerant.

Organic synthesis, ... refrigerant, solvent, grain and fruit fumigant.

The main commercial uses of ethyl bromide at present are as an ethylating agent & as a solvent in the chemical & pharmaceutical industries. Ethyl bromide has been used as a refrigerant. Human exposure to ethyl bromide has occurred during its use as an anesthetic, but widespread use for this purpose has been stopped.

Bromoethane is an industrial chemical.

U.S. Production · 4 件

2023: 1,000,000 - <8,500,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 1.36X10+6 GRAMS

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: ethyl bromide:

Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 2 件

Made by distilling from a mixture of HBr, ethyl alcohol and H2SO4; ... by phosphorus and bromine method.

... Ethyl bromide is produced by refluxing ethanol with hydrobromic acid, or with an alkali bromide and sulfuric acid. The reaction of ethane with sulfur trioxide and potassium bromide at 300-325 °C produces ethyl bromide with a 91% yield based on ethane.

Formulations/PreparationsGrade: Technical (98%)
General Manufacturing Information · 2 件

Not Known or Reasonably Ascertainable

Ethane, bromo-: ACTIVE

応用分野 · 9 件

解説C2H5Br(108.97).ハロゲン化アルキルの一つ。ブロモエタンは,エーテル臭の揮発性液体.引火点-20 ℃,融点-125.5 ℃,沸点38.4 ℃.d2041.4555.n20D1.4238.臭化エチル、エチルブロミドともよぶ。エタンの水素原子1個を臭素原子で置換したもの。無色の液体。水に難溶、エタノール(エチルアルコール)、ベンゼンなどの有機溶媒に可溶。経口・吸入ともに有毒(許容濃度200ppm)。エタノールに臭化水素酸と少量の硫酸を加えて蒸留すれば得られる。臭化エチルともいう.エタノールに臭化水素と硫酸とを加えて蒸留すると得られる.森北出版「化学辞典(第2版)

用途有機合成原料、冷凍剤

用途真用、I R 用測定粉末

用途ブロモエタンは,有機合成でエチル化剤として利用される。また、麻酔剤としても用いられる。

用途有機合成原料、医薬品、冷凍剤原料、農薬原料

説明Ethyl bromide is a colorless to yellow liquid that becomes a gas at temperatures above 101 °F (38 ℃). Ethyl bromide has an etherlike odor and a burning taste. Ethyl bromide is miscible with alcohols, ether, chloroform, and organic solvents; its water solubility is 9000 mg l-1 at 25 ℃. Ethyl bromide’s vapor density relative to air is 3.76.

使用Bromoethane is an alkylating agent primarily used as a chemical intermediate in organic synthesis, in the manufacture of pharmaceuticals, and for the ethylation of gasoline. To a lesser extent, it has been used as a fruit and grain fumigant, refrigerant, and solvent. Although proposed occasionally as a general anesthetic in the earlier part of this century, it has not been used to any extent for this purpose (Sayers et al., 1929; Abreu et al., 1939; ITII, 1979; Sittig, 1979; Torkelson and Rowe, 1981;Merck, 1983).

一般的な説明A colorless volatile liquid. Slightly soluble in water and denser than water. Flash point below 0°F. Vapors are heavier than air. Toxic by inhalation. Irritates skin and eyes. Used to make pharmaceuticals and as a solvent.

使用用途臭化エチルは、有機合成のためのエチル化剤として使用されています。例えば、カルボン酸塩からのエチルエステル合成やアミン類のエチル化によるエチルアミン合成などに使われています。 また、有機マグネシウムハロゲン化物であるグリニャール試薬 (英: Grignard reagent) の原料としても使用可能です。有機合成でグリニャール試薬は、欠かせない試薬として長年使われています。 医薬分野では医薬品の原料として使われ、麻酔薬に使われる場合もあります。

調製方法 · 3 件

製造方法Bromoethane is produced by the reaction of either hydrogen or potassium bromide with cold ethanol or with ethylene and sulfuric acid (Hawley, 1977; Sittig, 1979; Merck, 1983). It is commercially available at greater than 99% purity. Production from two U.S. manufacturers was estimated at 163.5 million pounds in 1986 (CSITC, 1987); no recent import and export information was available in the literature.

合成方法赤リンの存在下エタノールに臭素を徐々に作用させたあと,蒸留?精製する。触媒の存在下エチレンに臭化水素を付加させる方法もある

純化方法The main impurities are usually EtOH and water, both of which form azeotropes with it. Ethanol and unsaturated compounds can be removed by washing with conc H2SO4 until no further coloration is produced. The ethyl bromide is then washed with water, aqueous Na2CO3, and water again, then dried with CaCl2, MgSO4 or CaH2, and distilled from P2O5. Olefinic impurities can also be removed by storing the ethyl bromide in daylight with elemental bromine, later removing the free bromine by extraction with dilute aqueous Na2SO3, drying the ethyl bromide with CaCl2 and fractionally distilling it. Alternatively, unsaturated compounds can be removed by bubbling oxygen containing ca 5% ozone through the liquid for an hour, then washing with aqueous Na2SO3 to hydrolyse ozonides and remove hydrolysis products, followed by drying and distillation. [Beilstein 1 IV 150.]

上流・下流製品情報

下流製品

cis-6-ノネン-1-オールエチル フェニル スルフィドN,N-ジエチル-o-トルイジン1-エチル-3-メチルイミダゾリウムテトラフルオロボラート2-エチルマロン酸ジメチル4-アミノ-6-tert-ブチル-3-(エチルチオ)-1,2,4-トリアジン-5(4H)-オン2-エトキシベンズアルデヒドN-[3-(ジエチルアミノ)フェニル]アセトアミド1-エチル-3-メチルイミダゾリウムジシアナミドN,N-ジエチル-m-トルイジンエチニルマグネシウムブロミドN,N-ジエチル-p-トルイジン

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補足説明 · 1 件

定義ChEBI: Bromoethane is a bromoalkane that is ethane carrying a bromo substituent. It is an alkylating agent used as a chemical intermediate in various organic syntheses. It has a role as a carcinogenic agent, a solvent, a refrigerant, a local anaesthetic and an alkylating agent. It is a bromoalkane, a bromohydrocarbon and a volatile organic compound.

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