Record Information
Version1.0
Creation Date2009-06-22 16:08:38 UTC
Update Date2026-03-27 00:49:28 UTC
Accession NumberCHEM001551
Identification
Common Name1-Bromopropane
ClassSmall Molecule
Description1-bromopropane is an organobromide compound. It is a widely used organic solvent used for the cleaning of metal surfaces, removal of soldering residues from electronic circuit boards, and in the hole transport layer (HTL) of multi-layered OLEDs. It is also a solvent for adhesives and has been deployed as a replacement for perchloroethylene as a dry cleaning solvent. Its use as a solvent in aerosol glues used to glue foam cushions has been especially problematic. 1-bromopropane’s increasing use in the 21st century resulted from need for a substitute for chlorofluorocarbons and perchloroethylene (tetrachloroethylene). In 2013, a peer-review panel convened by the National Toxicology Program unanimously recommended that 1-bromopropane should be classified as a reasonably anticipated human carcinogen.
Contaminant Sources
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
N-Propyl bromideChEBI
1-BP, PropaneMeSH
Propyl bromideMeSH
N-PropylbromideMeSH
Chemical FormulaC3H7Br
Average Molecular Mass122.992 g/mol
Monoisotopic Mass121.973 g/mol
CAS Registry Number106-94-5
IUPAC Name1-bromopropane
Traditional Name1-bromopropane
SMILESCCCBr
InChI IdentifierInChI=1S/C3H7Br/c1-2-3-4/h2-3H2,1H3
InChI KeyCYNYIHKIEHGYOZ-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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-110°C
Boiling PointNot Available
Solubility2.45 mg/mL at 20°C [YALKOWSKY,SH & HE,Y (2003)]
Predicted Properties
PropertyValueSource
Water Solubility2.94 g/LALOGPS
logP2.18ALOGPS
logP1.9ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.57 m³·mol⁻¹ChemAxon
Polarizability9.49 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-0900000000-93ae8c951826e949031dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-ab167994627595e93149Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-7b7d969d767e9487c0f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-e80db58d1fdc9666b6c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-ac0f96881b04617b6332Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-303d9b4d82c8afc6ed07Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-01436ff6705673c9ce0eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
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. Alkylation of DNA by alkylbromides may also lead to mutations. 1-bromopropane reacts quickly with hepatic glutathione (GSH) leading to its rapid depletion and subsequent liver damage. Long-term exposure to 1-bromopropane decreases neurogenesis in the dentate gyrus which may contribute to the neurotoxicity. Downregulation of brain derived neurotrophic factor and glucocoritoid receptor mRNA expression and low hippocampal norepinephrine levels might contribute, at least in part, to the reduced neurogenesis.
Metabolism1-bromopropane is metabolized rapidly in the liver. Three mercapturic acids are produced: N-acetyl-S-propyl cysteine, N-acetyl-S-propyl cysteine-S-oxide and N-acetyl-S-(2-hydroxypropyl)cysteine. 1-bromopropoane also reacts rapidly with glutathione and can form glutathione conjugates.
Toxicity ValuesLD50: 2.5 g/kg (Intraperitoneal, Mouse) (7) LC50: 7000 ppm over 4 hours (Inhalation, Rat) (8)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesCleaning solvent, drycleaning solvent, aerosol glue solvent. 1-bromopropane may be found in products used in vapor and immersion degreasing operations for cleaning metal, plastics, electronic and optical components; in adhesive spray applications; and in dry cleaning operations. 1-bromopropane may also be a component of some aerosol spray products. Exposures to 1-bromopropane in occupational settings occur via two primary routes: (1) inhalation of 1-bromopropane vapors and mists; and (2) skin contact with 1-bromopropane.
Minimum Risk LevelNot Available
Health EffectsSkin irritation if contacts skin, redness and itching of skin and eyes. Acute exposure may lead to coughing, shortness of breath, headache, nausea, vomiting. Chronic exposure can lead to damage of the blood, liver and CNS. Neurotoxicity can arise due to chronic exposure through inhalation or skin. Human cases of 1-bromopropane (1-BP) toxicity exhibit ataxic gait and cognitive dysfunction, whereas rat studies showed pyknotic shrinkage in cerebellar Purkinje cells and electrophysiological changes in the hippocampus. Inhalation exposure to 1-bromopropane causes skin tumors in male rats, large intestine tumors in female and male rats, and lung tumors in female mice. 1-bromopropane, either directly or via reactive metabolites, can cause molecular alterations that typically are associated with carcinogenesis, including genotoxicity, oxidative stress, and glutathione depletion. Hepatotoxicity and reproductive toxicity have been noted in rodent studies.
SymptomsReported symptoms to overexposure include confusion, dysarthria, dizziness, paresthesias, and ataxia; unusual fatigue and headaches, development of arthralgias, visual disturbances (difficulty focusing), paresthesias, and muscular twitching. Symptoms may persist over one year after termination of exposure. Vapors may cause dizziness and suffocation. Inhalation of high concentrations may affect behavior/central nervous system (CNS depression) characterized by nausea, headache, dizziness, somnolence, unconsciousness and coma. It may also cause liver and kidney damage, lung injury, weight loss/ anorexia, bone marrow changes, and blood abnormalities.
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 LinkN-Propyl_bromide
Chemspider IDNot Available
ChEBI ID47105
PubChem Compound ID7840
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21830855
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22893012
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23183024
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23266320
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24438363