Bromoethane (T3D1784)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2014-12-24 20:24:38 UTC
Accession NumberT3D1784
Identification
Common NameBromoethane
ClassSmall Molecule
DescriptionBromoethane is an alkylating agent used primarily as a chemical intermediate in various organic syntheses. It is an organobromide (6).
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-BROMO-ETHANE
1-Bromoethane
BBX
Bromic ether
Bromodiborane
Bromoethane (ethyl bromide)
Bromure d'ethyle
C2H5Br
Ethyl bromide
Ethylbromide
Etylu bromek
Hydrobromic ether
Monobromoethane
Chemical FormulaC2H5Br
Average Molecular Mass108.965 g/mol
Monoisotopic Mass107.957 g/mol
CAS Registry Number74-96-4
IUPAC Namebromoethane
Traditional Namebromoethane
SMILESCCBr
InChI IdentifierInChI=1S/C2H5Br/c1-2-3/h2H2,1H3
InChI KeyInChIKey=RDHPKYGYEGBMSE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganobromides
Sub ClassNot Available
Direct ParentOrganobromides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organobromide
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-118.6°C
Boiling PointNot Available
Solubility9 mg/mL at 25°C [HORVATH,AL et al. (1999)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility10 g/LALOGPS
logP1.64ALOGPS
logP1.38ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity19.04 m³·mol⁻¹ChemAxon
Polarizability7.48 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-c1bedeae639647387f012016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-5f07bd6f0a6ee4cc80f12016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-6900000000-cac63e82cb1562a4db902016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-89867c9500dbb9a105652016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1900000000-4f322e75d73c0939b4e72016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-4900000000-e22a22db808680d636bd2016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9300000000-add6bbfcbc923f5212c82014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityOrganobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, 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. Alkylation of DNA by alkylbromides may also lead to mutations.
MetabolismNot Available
Toxicity ValuesLD50: 1350 mg/kg (Oral, Rat) (2) LD50: 1750 mg/kg (Intraperitoneal, Rat) (3) LC50: 27 000 ppm over 1 hours (Inhalation, Rat) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (8)
Uses/SourcesBromoethane is an industrial chemical.
Minimum Risk LevelNot Available
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 (1)
SymptomsInhalation can cause drowsiness and excessive amounts can lead to unconsciousness. Exposure to eyes can lead to redness and pain.
TreatmentEYES: 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.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6332
ChEMBL IDCHEMBL156378
ChemSpider ID6092
KEGG IDC19354
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-8985
CTD IDC037311
Stitch IDBromoethane
PDB IDNot Available
ACToR ID200
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1784.pdf
General References
  1. Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS No. 74-96-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1989 Oct;363:1-186. [12695778 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Clayton GD and Clayton FE (eds) (1993-1994). Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc.
  4. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  5. Wikipedia. Bromoethane. Last Updated 26 April 2009. [Link]
  6. Toxicity Information for Bromoethane [Link]
  7. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  8. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS No. 74-96-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1989 Oct;363:1-186. [12695778 ]
Target Details
2. Glutathione
References
  1. Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS No. 74-96-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1989 Oct;363:1-186. [12695778 ]
Target Details
3. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Toxicology and Carcinogenesis Studies of Bromoethane (Ethyl Bromide) (CAS No. 74-96-4) in F344/N Rats and B6C3F1 Mice (Inhalation Studies). Natl Toxicol Program Tech Rep Ser. 1989 Oct;363:1-186. [12695778 ]
  2. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]