Ethyl Bromide

HCID 6332CAS 74-96-4

Basic information

Standard SMILES
CCBr
InChIKey
RDHPKYGYEGBMSE-UHFFFAOYSA-N
Molecular formula
C2H5Br
Average molar mass
108.97 g/mol
Monoisotopic mass
107.95746226

Overview

Bromoethane can cause cancer according to The National Toxicology Program.

Names & identifiers

Preferred name
Ethyl Bromide
IUPAC
bromoethane
English name
Bromoethane
Molecular formula
C2H5Br
Molecular weight
108.96

Names & synonyms

Bromoethane74-96-4ETHYL BROMIDE1-BromoethaneEthane, bromo-Bromic etherMonobromoethaneHydrobromic etherBromure d'ethyleEtylu bromekHalon 2001NCI-C55481
Show more names
C2H5BrBromethanEthylbromid1-BromethanF160B1SINOBIOhalon2001Bromoethan
DTXSID6020199NCI-554813LI8384T9PHNSC-8824DTXCID60199CHEBI:47232BromoethanumRefChem:5617

Database identifiers

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

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
3

Experimental & physicochemical properties

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

log Kow = 1.61

1.61

Odor · 2 items

... Ether-like odor

Ethereal odor

TasteBurning taste

Physicochemical properties

Melting point
-119 °C · -119 °C
Boiling point
37 · 37-40 °C(lit.)
Density
1.46 g/mL · 1.46 g/mL at 25 °C(lit.)
vapor density
3.75 · ~3.75 (vs air)
vapor pressure
25.32 psi · 25.32 psi ( 55 °C)
refractive index
20 · n20/D 1.425(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 6 items

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 items

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 items

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

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

Safety & protection

Fire Fighting · 2 items

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

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 items

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 items

· 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 items

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).

Toxicology

Body Burden · 1 item

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 item

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 item

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 items

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).

Regulatory information

TSCA Requirements · 2 items

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 item

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

Safety data

F
8
PPE
Eyeshields, Faceshields, Gloves
wgk
1
IDLA
2,000 ppm
tsca
TSCA listed
rtecs
KH6475000

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 5 items

... 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 items

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.

Uses & manufacturing

Uses · 5 items

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 items

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 items

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 items

Not Known or Reasonably Ascertainable

Ethane, bromo-: ACTIVE

Applications · 4 items

DescriptionEthyl 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.

UsesEthyl bromide is used as a refrigerant and asan ethylating agent. It was formerly used asa topical anesthetic.

UsesBromoethane 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).

General DescriptionA 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.

Preparation methods · 1 item

PreparationBromoethane 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
南京兰亚化工贸易有限公司+86-25-8331-5620 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

1,513 records

Linked notes

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