2-Bromopropane (CHEM001538)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (3)XML
Record Information
Version1.0
Creation Date2009-06-22 16:08:36 UTC
Update Date2026-03-27 01:36:49 UTC
Accession NumberCHEM001538
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.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Isopropyl bromideMeSH
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 KeyNAMYKGVDVNBCFQ-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)]
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-72270e20f9ab3f239917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-ecb0e72c1244b00ecc30Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-4900000000-5a4045d4815615974986Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-1174a1972c8f4561a61aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-d746b49f3e0a7453451aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-49757f306ce3341f4fd5Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-f9ae541884fd9d0035bbSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3) ; dermal (3)
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) (5) LD50: >2000 mg/kg (Oral, Rat) (6) LC50: 31 171 ppm over 4 hours (Inhalation, Mouse) (6)
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.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2-Bromopropane
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID6358
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available