ContaminantDB: 1-Bromobutane

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-06-22 16:08:36 UTC

Update Date

2026-03-27 00:38:28 UTC

Accession Number

CHEM001531

Identification

Common Name

1-Bromobutane

Class

Small Molecule

Description

1-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.

Contaminant Sources

HPV EPA Chemicals
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Bromide Compound
Industrial/Workplace Toxin
Lachrymator
Organic Compound
Organobromide
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Butylbromide	MeSH
Butyl bromide	MeSH
1-bromo-Butane	ChEMBL

Chemical Formula

C₄H₉Br

Average Molecular Mass

137.018 g/mol

Monoisotopic Mass

135.989 g/mol

CAS Registry Number

109-65-9

IUPAC Name

1-bromobutane

Traditional Name

1-bromobutane

SMILES

CCCCBr

InChI Identifier

InChI=1S/C4H9Br/c1-2-3-4-5/h2-4H2,1H3

InChI Key

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.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organobromides

Sub Class

Not Available

Direct Parent

Organobromides

Alternative Parents

Substituents

Hydrocarbon derivative
Organobromide
Alkyl halide
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	-112.4°C
Boiling Point	Not Available
Solubility	0.869 mg/mL at 25°C [YALKOWSKY,SH & HE,Y (2003)]

Predicted Properties

Property	Value	Source
Water Solubility	0.77 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.35	ChemAxon
logS	-2.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	28.17 m³·mol⁻¹	ChemAxon
Polarizability	11.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-a8325637cda4ca52e5c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900000000-79cf4e86cc12624efc8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9200000000-8d3d4afefa2e77947856	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-1900000000-f6ed99a52ac552fae318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4900000000-ea2aed785aa57a155fc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9100000000-1e148ab1bc0e16f84962	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-056r-9000000000-f5c230a922ae152a3c69	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

1-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.

Metabolism

Rabbits 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 Values

LD50: 2761 mg/kg (Oral Rat) (1) LC50: 237 g/m3 over 30 minutes (Inhalation, Rat) (7)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Hepatoxic, 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.

Symptoms

Skin irritation if contacts skin, redness and itching of skin and eyes. Acute exposure may lead to coughing, shortness of breath, headache, nausea, vomiting

Treatment

EYES: 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

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

1-Bromobutane

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

8002

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

1-Bromobutane (CHEM001531)

Structure for CHEM001531: 1-Bromobutane