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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:39:41 UTC
Update Date2019-01-11 20:01:52 UTC
HMDB IDHMDB0041792
Secondary Accession Numbers
  • HMDB41792
Metabolite Identification
Common Name1,3-Butadiene
Description1,3-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.
Structure
Data?1547236912
Synonyms
ValueSource
1,3-ButadienChEBI
alpha,gamma-ButadieneChEBI
BivinylChEBI
Buta-1,3-dienChEBI
CH2=ch-CH=ch2ChEBI
DivinylChEBI
VinylethyleneChEBI
a,g-ButadieneGenerator
α,γ-butadieneGenerator
alpha,«gamma»-butadieneHMDB
BiethyleneHMDB
Buta-1,3-dieenHMDB
Buta-1,3-dieneHMDB
ButadieenHMDB
ButadienHMDB
ButadieneHMDB
CH22CH1CH2CH2HMDB
CH2=chch=ch2HMDB
ErythreneHMDB
PyrrolyleneHMDB
Chemical FormulaC4H6
Average Molecular Weight54.0904
Monoisotopic Molecular Weight54.046950192
IUPAC Namebuta-1,3-diene
Traditional Name1,3-butadiene
CAS Registry Number106-99-0
SMILES
C=CC=C
InChI Identifier
InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2
InChI KeyKAKZBPTYRLMSJV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkadienes. These are acyclic hydrocarbons that contain exactly two carbon-to-carbon double bonds.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentAlkadienes
Alternative Parents
Substituents
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Route of exposure:

Role

Indirect biological role:

Environmental role:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.74 mg/mL at 25 °CNot Available
LogP1.99Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.98 g/LALOGPS
logP1.94ALOGPS
logP1.63ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.29 m³·mol⁻¹ChemAxon
Polarizability6.7 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ecView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ufr-9000000000-cddbfceffd529008d5ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-9000000000-e4f51ef2fbf933007d39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-805abc61b7c8de6c5789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-805abc61b7c8de6c5789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-46aa55de9e12fa462b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-9000000000-191296d0bc49a4a79c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-9000000000-191296d0bc49a4a79c02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-9000000000-7031b766ca514dc531b4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-9000000000-cfc5558b93570d1d78c0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7557
KEGG Compound IDC16450
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1,3-Butadiene
METLIN IDNot Available
PubChem Compound7845
PDB IDNot Available
ChEBI ID39478
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang ZC, Zhang X, Yu QY, Liu ZC, Xu CM, Gao JS, Zhuang J, Wang X: Pd cluster nanowires as highly efficient catalysts for selective hydrogenation reactions. Chemistry. 2012 Feb 27;18(9):2639-45. doi: 10.1002/chem.201102903. Epub 2012 Jan 26. [PubMed:22282407 ]