1,3-butadiene
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| Names | |||
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Preferred IUPAC name
Buta-1,3-diene
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| Other names
Biethylene
Erythrene Divinyl Vinylethylene Bivinyl Butadiene |
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| Identifiers | |||
106-99-0 
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| 3D model (Jmol) | Interactive image | ||
| ChEBI |
CHEBI:39478
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| ChEMBL |
ChEMBL537970
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| ChemSpider |
7557
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| ECHA InfoCard | 100.003.138 | ||
| EC Number | 271-039-0 | ||
| KEGG |
C16450
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| PubChem | 7845 | ||
| RTECS number | EI9275000 | ||
| UNII |
JSD5FGP5VD
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| UN number | 1010 | ||
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| Properties | |||
| C4H6 | |||
| Molar mass | 54.0916 g/mol | ||
| Appearance | Colourless gas or refrigerated liquid |
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| Odor | mildly aromatic or gasoline-like | ||
| Density | 0.6149 g/cm3 at 25 °C, solid 0.64 g/cm3 at −6 °C, liquid |
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| Melting point | −108.9 °C (−164.0 °F; 164.2 K) | ||
| Boiling point | −4.4 °C (24.1 °F; 268.8 K) | ||
| 0.735 g/100 mL | |||
| Solubility | very soluble in acetone soluble in ether, ethanol |
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| Vapor pressure | 2.4 atm (20°C) | ||
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Refractive index (nD)
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1.4292 | ||
| Viscosity | 0.25 cP at 0 °C | ||
| Hazards | |||
| Main hazards | Flammable, irritative, carcinogen | ||
| Safety data sheet |
See: data page ECSC 0017 |
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| R-phrases | R45 R46 R12 | ||
| S-phrases | S45 S53 | ||
| NFPA 704 | |||
| Flash point | −85 °C (−121 °F; 188 K) liquid flash point | ||
| 420 °C (788 °F; 693 K) | |||
| Explosive limits | 2–12% | ||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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548 mg/kg (rat, oral) | ||
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LC50 (median concentration)
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115,111 ppm (mouse) 122,000 ppm (mouse, 2 hr) 126,667 ppm (rat, 4 hr) 130,000 ppm (rat, 4 hr) |
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LCLo (lowest published)
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250,000 ppm (rabbit, 30 min) | ||
| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 1 ppm ST 5 ppm | ||
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REL (Recommended)
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potential occupational carcinogen | ||
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IDLH (Immediate danger)
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2000 ppm | ||
| Related compounds | |||
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Isoprene Chloroprene |
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Related compounds
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Butane | ||
| Supplementary data page | |||
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Refractive index (n), Dielectric constant (εr), etc. |
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Thermodynamic
data |
Phase behaviour solid–liquid–gas |
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| UV, IR, NMR, MS | |||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is  ?) |
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| Infobox references | |||
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. The molecule can be viewed as two vinyl groups (CH2=CH2) joined together. The word butadiene usually refers to 1,3-butadiene which has the structure H2C=CH−CH=CH2.
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. The EPA lists it as the "mobile source air toxic" with the highest normalized risk factor, exceeding that of formaldehyde, the second riskiest air toxic emitted by motor vehicles, by a factor of more than 20.
The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. 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. The rest of this article concerns only 1,3–butadiene.
In 1863, the French chemist E. Caventou isolated a previously unknown hydrocarbon from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene, and obtained a material with rubber-like properties. This polymer was, however, found to be too soft to replace natural rubber in many applications, notably automobile tires.
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