ContaminantDB: 1,3-Butadiene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:11 UTC

Update Date

2026-03-27 01:40:36 UTC

Accession Number

CHEM000143

Identification

Common Name

1,3-Butadiene

Class

Small Molecule

Description

1,3-Butadiene is a simple conjugated diene with the formula C4H6. It is an important industrial chemical used as a monomer in the production of synthetic rubber. When the word butadiene is used, most of the time it refers to 1,3-butadiene. 1,3-Butadiene is inconvenient for laboratory use because it is a flammable gas subject to polymerization on storage. 3-Butadiene cyclic sulfone (sulfolene) is a convenient solid storable source for 1,3-butadiene for many laboratory purposes when the generation of sulfur dioxide byproduct in the reaction mixture is not objectionable. Long-term exposure has been associated with cardiovascular disease, there is a consistent association with leukemia, and weaker association with other cancers. Most butadiene is polymerized to produce synthetic rubber. While polybutadiene itself is a very soft, almost liquid material, copolymers prepared from mixtures of butadiene with styrene and/or acrylonitrile, such as acrylonitrile butadiene styrene (ABS), acrylonitrile butadiene (NBR) and styrene-butadiene (SBR) are tough and elastic. SBR is the material most commonly used for the production of automobile tires. Smaller amounts of butadiene are used to make the nylon intermediate, adiponitrile, by the addition of a molecule of hydrogen cyanide to each of the double bonds in a process called hydrocyanation developed by DuPont. Other synthetic rubber materials such as chloroprene, and the solvent sulfolane are also manufactured from butadiene. Butadiene is used in the industrial production of 4-vinylcyclohexene via a Diels Alder dimerization reaction and the vinylcyclohexene is a common impurity found in butadiene upon storage. Cyclooctadiene and cyclododecatriene are produced via nickel- or titanium-catalyzed dimerization and trimerization reactions, respectively. Butadiene is also useful in the synthesis of cycloalkanes and cycloalkenes, as it reacts with double and triple carbon-carbon bonds through the Diels-Alder reaction. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene. However, this allene is difficult to prepare and has no industrial significance. This diene is also not expected to act as a diene in a Diels-Alder reaction due to its structure. To effect a Diels-Alder reaction only a conjugated diene will suffice.

Contaminant Sources

Clean Air Act Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 1
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds

Contaminant Type

Cigarette Toxin
Household Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Lachrymator
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,3-Butadien	ChEBI
alpha,gamma-Butadiene	ChEBI
Bivinyl	ChEBI
Buta-1,3-dien	ChEBI
CH2=ch-CH=ch2	ChEBI
Divinyl	ChEBI
Vinylethylene	ChEBI
a,g-Butadiene	Generator
Α,γ-butadiene	Generator
alpha,«gamma»-butadiene	HMDB
Biethylene	HMDB
Buta-1,3-dieen	HMDB
Buta-1,3-diene	HMDB
Butadieen	HMDB
Butadien	HMDB
Butadiene	HMDB
CH22CH1CH2CH2	HMDB
CH2=chch=ch2	HMDB
Erythrene	HMDB
Pyrrolylene	HMDB
1,3-Butadiene	ChEBI

Chemical Formula

C₄H₆

Average Molecular Mass

54.090 g/mol

Monoisotopic Mass

54.047 g/mol

CAS Registry Number

106-99-0

IUPAC Name

buta-1,3-diene

Traditional Name

1,3-butadiene

SMILES

C=CC=C

InChI Identifier

InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2

InChI Key

KAKZBPTYRLMSJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alkadienes. These are acyclic hydrocarbons that contain exactly two carbon-to-carbon double bonds.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Unsaturated hydrocarbons

Sub Class

Olefins

Direct Parent

Alkadienes

Alternative Parents

Unsaturated aliphatic hydrocarbons

Substituents

Alkadiene
Unsaturated aliphatic hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butadiene (CHEBI:39478 )
a small molecule (BUTADIENE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless gas.

Experimental Properties

Property	Value
Melting Point	-108.9°C
Boiling Point	Not Available
Solubility	0.735 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.63	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	20.29 m³·mol⁻¹	ChemAxon
Polarizability	6.7 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
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-9000000000-cddbfceffd529008d5ec	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ufr-9000000000-cddbfceffd529008d5ec	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-9000000000-e4f51ef2fbf933007d39	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-805abc61b7c8de6c5789	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-805abc61b7c8de6c5789	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-46aa55de9e12fa462b49	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-9000000000-191296d0bc49a4a79c02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9000000000-191296d0bc49a4a79c02	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-7031b766ca514dc531b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-9000000000-0d737e29499be7940207	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-9000000000-0d737e29499be7940207	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-0d737e29499be7940207	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-1924391f943e092b4486	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-c60974066ebc2547dd57	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-9000000000-45337fddf4aab37b4ba0	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-9000000000-cfc5558b93570d1d78c0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (7)

Mechanism of Toxicity

Certain metabolites of 1,3-butadiene have been shown to bind to DNA and nucleoproteins, forming protein-DNA and DNA-DNA crosslinks. Specifically, 1,2-epoxybutene-3 and diepoxybutane react with guanine to cause crosslinking. (7, 1)

Metabolism

1,3-Butadiene is absorbed following inhalation and is distributed to the adipose tissue, brain, liver, septum, and kidney. 1,3-Butadiene is believed to be metabolized in the liver by cytochrome P-450 enzymes, forming 1,2-epoxybutene-3 as the main metabolite. 1,2-Epoxybutene-3 is further transformed into 3-butene-1,2-diol by microsomal epoxide hydrolase. The metabolites of 1,3-butadiene are exhaled as carbon dioxide or excreted in the urine. (7)

Toxicity Values

LD50: 3.21 g/kg (Oral, Mouse) (4) LC50: 270 000 mg/m3 over 2 hours (Inhalation, Mouse) (4)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

1, carcinogenic to humans. (6)

Uses/Sources

1,3-Butadiene is made from the processing of petroleum. It is used mainly to make synthetic rubber for tires. It is also used to make plastics such as acrylics, and small amounts can be found in gasoline. (7)

Minimum Risk Level

Not Available

Health Effects

Breathing high levels of 1,3-butadiene causes central nervous system damage. Chronic exposure may also cause lung damage and kidney, liver, and cardiovascular disease. In addition, 1,3-butadiene is a known human carcinogen. (7)

Symptoms

Breathing 1,3-butadiene may cause irritation of the eyes, nose, and throat. High levels of 1,3-butadiene can also cause, blurred vision, nausea, fatigue, headache, decreased blood pressure and pulse rate, and unconsciousness. Skin contact with liquid 1,3-butadiene can cause irritation and frostbite. (7)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0041792

FooDB ID

Not Available

Phenol Explorer ID