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Butadiene information


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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
CAS Number
  • 106-99-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 605258
ChEBI
  • CHEBI:39478 checkY
ChEMBL
  • ChEMBL537970 checkY
ChemSpider
  • 7557 checkY
ECHA InfoCard 100.003.138 Edit this at Wikidata
EC Number
  • 271-039-0
Gmelin Reference
 25198
KEGG
  • C16450 checkY
PubChem CID
  • 7845
RTECS number
  • EI9275000
UNII
  • JSD5FGP5VD checkY
UN number 1010
CompTox Dashboard (EPA)
  • DTXSID3020203 Edit this at Wikidata
InChI
  • 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
SMILES
  • C=CC=C
Properties[4]
Chemical formula
 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)
Solubility in water
 1.3 g/L at 5 °C, 735 mg/L at 20 °C
Solubility
  • Very soluble in acetone
  • Soluble in ether, ethanol
Vapor pressure 2.4 atm (20 °C)[3]
Refractive index (nD)
 1.4292
Viscosity 0.25 cP at 0 °C
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Flammable, irritative, carcinogen
GHS labelling:[7]
Pictograms
 GHS02: Flammable GHS08: Health hazard GHS04: Compressed Gas
Signal word
 Danger
Hazard statements
 H220, H280, H340, H350
Precautionary statements
 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]
Autoignition
temperature
 414 °C (777 °F; 687 K)[6]
Explosive limits 2–12%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 548 mg/kg (rat, oral)
LC50 (median concentration)
  • 115,111 ppm (mouse)
  • 122,000 ppm (mouse, 2 h)
  • 126,667 ppm (rat, 4 h)
  • 130,000 ppm (rat, 4 h)[5]
LCLo (lowest published)
 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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

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Chloroprene

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whom they collaborated. Chloroprene is produced in three steps from 1,3-butadiene: (i) chlorination, (ii) isomerization of part of the product stream, and...

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Polystyrene

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has a high butylene content, styrene-butadiene rubber (SBR) is formed. The impact strength of styrene-butadiene co-polymers is based on phase separation...

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Diene

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polyenes. Polyenes and dienes share many properties. On an industrial scale, butadiene is prepared by thermal cracking of butanes. In a similarly non-selective...

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Acetonitrile

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Dimethylbutadiene

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Hexachlorobutadiene

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equilibrium. The electrophilic addition reaction of hydrogen bromide to 1,3-butadiene above room temperature leads predominantly to the thermodynamically more...

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C4H6

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