2-Bromopropane (T3D1788)

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 NumberT3D1788
Identification
Common Name2-Bromopropane
ClassSmall Molecule
Description2-Bromopropane is an organobromide compound. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is sometimes used as an alternative to ozone-depleting cleaning solvents such as chlorofluorocarbons. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-BROMO-PROPANE
iso-C3H7Br
Isopropyl bromide
Isopropylbromide
Sec-propyl bromide
Chemical FormulaC3H7Br
Average Molecular Mass122.992 g/mol
Monoisotopic Mass121.973 g/mol
CAS Registry Number75-26-3
IUPAC Name2-bromopropane
Traditional Name2-bromopropane
SMILESCC(C)Br
InChI IdentifierInChI=1S/C3H7Br/c1-3(2)4/h3H,1-2H3
InChI KeyInChIKey=NAMYKGVDVNBCFQ-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-89°C
Boiling PointNot Available
Solubility3.18 mg/mL at 20°C [YALKOWSKY,SH & HE,Y (2003)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.34 g/LALOGPS
logP1.83ALOGPS
logP1.79ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability9.34 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, Positivesplash10-00di-0900000000-72270e20f9ab3f2399172016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-ecb0e72c1244b00ecc302016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-4900000000-5a4045d48156159749862016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-1174a1972c8f4561a61a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d746b49f3e0a7453451a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-49757f306ce3341f4fd52016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f9ae541884fd9d0035bb2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, benzene, 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. 2-bromopropane triggers the mitochondrion-dependent apoptotic pathway via ROS (reactive oxygen species) generation. 2-bromopropane has also been shown to induce DNA damage, impair functional antioxidant cellular defenses, and enhance the lipid peroxidation in cultured Leydig cells.
MetabolismNot Available
Toxicity ValuesLD50: 4837 mg/kg (Intraperitoneal, Mouse) (3) LD50: >2000 mg/kg (Oral, Rat) (4) LC50: 31 171 ppm over 4 hours (Inhalation, Mouse) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources2-Bromopropane is an industrial and laboratory chemical.
Minimum Risk LevelNot Available
Health Effects2-Bromopropane is a strong lachrymator. Chronic exposure has been shown to have teratogenic effects in mouse and rat embryos. Very high chronic doses led to developmental toxicity which included an increase in the fetal deaths, a decrease in the litter size, and a reduction in the fetal body weight. In addition, an increase in the incidence of fetal external, visceral, and skeletal abnormalities was seen. Chronic exposure to 2-bromopropane depletes spermatogenic cells in male rats and oocytes in female rats. Humans exposed to 2-bromopropane exhibited oligospermia, amenorrhea and other reproductive toxic effects.
SymptomsMay cause skin, eye and respiratory tract irritation. May affect behavior/central nervous system (central nervous system depression, excitement fatigue, headache, dizziness, stupor,unconsciousness and possible coma). If ingested, 2-bromopropane may cause gastrointestinal tract irritation with nausea, and vomiting. It may also affect behavior/central nervous system with symptoms similar to those for inhalation. May also cause kidney damage and liver damage.
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 ID6358
ChEMBL IDCHEMBL451810
ChemSpider ID6118
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDBETA-AMINOPROPIONITRILE
CTD IDC103736
Stitch ID2-Bromopropane
PDB IDNot Available
ACToR ID6864
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1788.pdf
General References
  1. NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of 2-Bromopropane (2-BP). NTP CERHR MON. 2003 Dec;(10):i-III11. [15995734 ]
  2. Chan WH: Resveratrol protects against 2-bromopropane-induced apoptosis and disruption of embryonic development in blastocysts. Int J Mol Sci. 2011;12(8):4991-5010. doi: 10.3390/ijms12084991. Epub 2011 Aug 5. [21954340 ]
  3. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  4. American Conference of Governmental Industrial Hygienists (2008). TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  5. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  6. Wikipedia. 2-Bromopropane. Last Updated 5 June 2009. [Link]
  7. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated GenesNot Available
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. Chan WH: Resveratrol protects against 2-bromopropane-induced apoptosis and disruption of embryonic development in blastocysts. Int J Mol Sci. 2011;12(8):4991-5010. doi: 10.3390/ijms12084991. Epub 2011 Aug 5. [21954340 ]
  2. NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of 2-Bromopropane (2-BP). NTP CERHR MON. 2003 Dec;(10):i-III11. [15995734 ]
Target Details
2. Glutathione
References
  1. Chan WH: Resveratrol protects against 2-bromopropane-induced apoptosis and disruption of embryonic development in blastocysts. Int J Mol Sci. 2011;12(8):4991-5010. doi: 10.3390/ijms12084991. Epub 2011 Aug 5. [21954340 ]
  2. NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of 2-Bromopropane (2-BP). NTP CERHR MON. 2003 Dec;(10):i-III11. [15995734 ]
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. Chan WH: Resveratrol protects against 2-bromopropane-induced apoptosis and disruption of embryonic development in blastocysts. Int J Mol Sci. 2011;12(8):4991-5010. doi: 10.3390/ijms12084991. Epub 2011 Aug 5. [21954340 ]
  2. NTP-CERHR Monograph on the Potential Human Reproductive and Developmental Effects of 2-Bromopropane (2-BP). NTP CERHR MON. 2003 Dec;(10):i-III11. [15995734 ]
  3. 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 ]