Butadiene

"Divinyl" redirects here. For the band, see Divinyls.

1,3-Butadiene
Full structural formula of 1,3-butadiene
Full structural formula of 1,3-butadiene
Skeletal formula of 1,3-butadiene
Skeletal formula of 1,3-butadiene
Ball-and-stick model of 1,3-butadiene
Ball-and-stick model of 1,3-butadiene
Space-filling model of 1,3-butadiene
Space-filling model of 1,3-butadiene
Names
Preferred IUPAC name
Buta-1,3-diene[1]
Other names
  • Biethylene
  • Erythrene
  • Divinyl
  • Vinylethylene
  • Bivinyl
  • Butadiene
Identifiers
3D model (JSmol)
605258
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.138 Edit this at Wikidata
EC Number
  • 271-039-0
25198
KEGG
RTECS number
  • EI9275000
UNII
UN number 1010
  • InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2 checkY
    Key: KAKZBPTYRLMSJV-UHFFFAOYSA-N checkY
  • InChI=1/C4H6/c1-3-4-2/h3-4H,1-2H2
    Key: KAKZBPTYRLMSJV-UHFFFAOYAZ
  • C=CC=C
Properties[4]
C4H6
CH2=CH-CH=CH2
Molar mass 54.0916 g/mol
Appearance Colourless gas
or refrigerated liquid
Odor Mildly aromatic or gasoline-like
Density
  • 0.6149 g/cm3 at 25 °C, p>1 atm[2]
  • 0.64 g/cm3 at −6 °C, liquid
Melting point −108.91 °C (−164.04 °F; 164.24 K)
Boiling point −4.41 °C (24.06 °F; 268.74 K)
1.3 g/L at 5 °C, 735 mg/L at 20 °C
Solubility
Vapor pressure 2.4 atm (20 °C)[3]
1.4292
Viscosity 0.25 cP at 0 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, irritative, carcinogen
GHS labelling:[7]
GHS02: Flammable GHS08: Health hazard
Danger
H220, H340, H350
P202, P210, P280, P308+P313, P377, P381, P403
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
4
2
Flash point −85 °C (−121 °F; 188 K) liquid flash point[3]
414 °C (777 °F; 687 K)[6]
Explosive limits 2–12%
Lethal dose or concentration (LD, LC):
548 mg/kg (rat, oral)
  • 115,111 ppm (mouse)
  • 122,000 ppm (mouse, 2 h)
  • 126,667 ppm (rat, 4 h)
  • 130,000 ppm (rat, 4 h)[5]
250,000 ppm (rabbit, 30 min)[5]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 ppm ST 5 ppm[3]
REL (Recommended)
 Potential occupational carcinogen[3]
IDLH (Immediate danger)
 2000 ppm[3]
Safety data sheet (SDS) ECSC 0017
Related compounds
Related Alkenes
and dienes
 Isoprene
Chloroprene
Related compounds
 Butane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3-Butadiene (/ˌbjuːtəˈdaɪiːn/)[8] is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber.[9] The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene.

Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles.[10]

The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance.

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 374. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Haynes, William M. (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton: CRC Press. p. 3-76. ISBN 978-1-4987-5429-3.
  3. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0067". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ "1,3-Butadiene". NIST Chemistry WebBook.
  5. ^ a b "1,3-Butadiene". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  6. ^ "1,3-Butadiene". INCHEM. International Programme on Chemical Safety (IPCS).
  7. ^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  8. ^ "BUTADIENE | Meaning & Definition for UK English". Lexico.com. Archived from the original on 20 August 2020. Retrieved 24 August 2022.
  9. ^ PubChem. "1,3-Butadiene". pubchem.ncbi.nlm.nih.gov. Retrieved 8 May 2024.
  10. ^ "1,3-Butadiene". US Environmental Protection Agency US EPA. Retrieved 2 September 2014.