1-Bromobutane (T3D1781)

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 20:24:37 UTC
Accession NumberT3D1781
Identification
Common Name1-Bromobutane
ClassSmall Molecule
Description1-Bromobutane is a colorless liquid that is insoluble in water, but soluble in ethanol and diethyl ether. As a primary haloalkane, it is especially prone to SN2 type reactions. It is commonly used as an alkylating agent, or in combination with magnesium metal in dry ether (Grignard reagent) to form carbon-carbon bonds. It can be used as a cleaning agent, an agent for chemical synthesis or as a solvent for extractions. It is highly flammable.
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-BUTANE
1-Butyl bromide
BBU
Bromo butane
Bromobutane
Butyl bromide
N-butyl bromide
N-butylbromide
n-C4H9Br
Chemical FormulaC4H9Br
Average Molecular Mass137.018 g/mol
Monoisotopic Mass135.989 g/mol
CAS Registry Number109-65-9
IUPAC Name1-bromobutane
Traditional Name1-bromobutane
SMILESCCCCBr
InChI IdentifierInChI=1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3
InChI KeyInChIKey=MPPPKRYCTPRNTB-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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-112.4°C
Boiling PointNot Available
Solubility0.869 mg/mL at 25°C [YALKOWSKY,SH & HE,Y (2003)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP2.73ALOGPS
logP2.35ChemAxon
logS-2.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.17 m³·mol⁻¹ChemAxon
Polarizability11.5 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, Positivesplash10-000i-0900000000-a8325637cda4ca52e5c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-79cf4e86cc12624efc8c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9200000000-8d3d4afefa2e779478562016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1900000000-f6ed99a52ac552fae3182016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4900000000-ea2aed785aa57a155fc52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-1e148ab1bc0e16f849622016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-f5c230a922ae152a3c692014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50.18 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (9) ; inhalation (9) ; dermal (9)
Mechanism of Toxicity1-bromobutane reacts quickly with hepatic glutathione (GSH) leading to its rapid depletion. This can cause liver damage and has been shown to increase serum levels of alanine aminotransferase and aspartate aminotransferase. Hepatic contents of thiobarbituric acid reactive substances can also be significantly increased. Splenic GSH levels can also be significantly reduced by single treatment with 1-bromobutane. S-Butyl GSH conjugates were detected in spleen from 6 hr after treatment. Oral 1-bromobutane significantly suppressed the antibody response to a T-dependent antigen and the production of splenic intracellular interlukin-2.
MetabolismRabbits and rats dosed with 1-bromobutane excrete in urine, in addition to butylmercapturic acid, (2-hydroxybutyl)mercapturic acid, (3-hydroxybutyl)mercapturic acid and 3-(butylthio)lactic acid. In the rabbit about 14% and in the rat about 22% of the dose of 1-bromobutane is excreted in the form of the hydroxymercapturic acids. 1-bromobutane also forms glutathione conjugates. Three kinds of GSH conjugates, including S-butyl GSH, S-butyl cysteine, and (hydroxybutyl)mercapturic acid, have been identified in mice livers after oral dosing with 375-1500 mg/kg of the compound.
Toxicity ValuesLD50: 2761 mg/kg (Oral Rat) (4) LC50: 237 g/m3 over 30 minutes (Inhalation, Rat) (5)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsHepatoxic, immunotoxic when ingested orally. Can cause lung damage and mucous membranes over extended periods/chronic exposures. Can cause skin and eye irritation. Not a carcinogen nor a mutagen nor a teratogen.
SymptomsSkin irritation if contacts skin, redness and itching of skin and eyes. Acute exposure may lead to coughing, shortness of breath, headache, nausea, vomiting
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 ID8002
ChEMBL IDCHEMBL160949
ChemSpider ID7711
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-622
CTD IDC047757
Stitch ID1-Bromobutane
PDB IDNot Available
ACToR ID1831
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1781.pdf
General References
  1. James SP, Jeffery DA, Waring RH, Wood PB: Some metabolites of 1-bromobutane in the rabbit and the rat. Biochem J. 1968 Oct;109(5):727-36. [5696863 ]
  2. Lee SK, Lee DJ, Ko GS, Yoo SH, Ha HW, Kang MJ, Jeong TC: Role of glutathione conjugation in 1-bromobutane-induced hepatotoxicity in mice. Food Chem Toxicol. 2010 Oct;48(10):2707-11. doi: 10.1016/j.fct.2010.06.044. Epub 2010 Jun 30. [20600521 ]
  3. Lee SK, Lee DJ, Jeon TW, Ko GS, Yoo SH, Ha HW, Kang MJ, Kang W, Kim SK, Jeong TC: Role of Glutathione Conjugation in 1-Bromobutane-induced Immunotoxicity in Mice. Toxicol Res. 2010 Jun;26(2):101-8. doi: 10.5487/TR.2010.26.2.101. [24278512 ]
  4. Harrison EH: Mechanisms of digestion and absorption of dietary vitamin A. Annu Rev Nutr. 2005;25:87-103. [16011460 ]
  5. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  6. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  7. Albright & Wilson Inc. (1992). Initial Submission: Acute Oral Toxicity Study with N-Butyl Bromide in Rats (Final Report) with Cover Letter.
  8. Wikipedia. 1-Bromobutane. Last Updated 13 April 2009. [Link]
  9. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [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. James SP, Jeffery DA, Waring RH, Wood PB: Some metabolites of 1-bromobutane in the rabbit and the rat. Biochem J. 1968 Oct;109(5):727-36. [5696863 ]
  2. Lee SK, Lee DJ, Ko GS, Yoo SH, Ha HW, Kang MJ, Jeong TC: Role of glutathione conjugation in 1-bromobutane-induced hepatotoxicity in mice. Food Chem Toxicol. 2010 Oct;48(10):2707-11. doi: 10.1016/j.fct.2010.06.044. Epub 2010 Jun 30. [20600521 ]
  3. Lee SK, Lee DJ, Jeon TW, Ko GS, Yoo SH, Ha HW, Kang MJ, Kang W, Kim SK, Jeong TC: Role of Glutathione Conjugation in 1-Bromobutane-induced Immunotoxicity in Mice. Toxicol Res. 2010 Jun;26(2):101-8. doi: 10.5487/TR.2010.26.2.101. [24278512 ]
Target Details
2. Glutathione
References
  1. James SP, Jeffery DA, Waring RH, Wood PB: Some metabolites of 1-bromobutane in the rabbit and the rat. Biochem J. 1968 Oct;109(5):727-36. [5696863 ]
  2. Lee SK, Lee DJ, Ko GS, Yoo SH, Ha HW, Kang MJ, Jeong TC: Role of glutathione conjugation in 1-bromobutane-induced hepatotoxicity in mice. Food Chem Toxicol. 2010 Oct;48(10):2707-11. doi: 10.1016/j.fct.2010.06.044. Epub 2010 Jun 30. [20600521 ]
  3. Lee SK, Lee DJ, Jeon TW, Ko GS, Yoo SH, Ha HW, Kang MJ, Kang W, Kim SK, Jeong TC: Role of Glutathione Conjugation in 1-Bromobutane-induced Immunotoxicity in Mice. Toxicol Res. 2010 Jun;26(2):101-8. doi: 10.5487/TR.2010.26.2.101. [24278512 ]
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. 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 ]