157 1,3-Butadiene 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. 106-99-0 7845 C4H6 54.046950 Colorless gas. -108.9°C 0.735 mg/mL at 25°C Inhalation (L990) 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. (L990, A293) 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. (L990) LD50: 3.21 g/kg (Oral, Mouse) (A598) LC50: 270 000 mg/m3 over 2 hours (Inhalation, Mouse) (A598) 1, carcinogenic to humans. (L135) 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. (L990) 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. (L990) 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. (L990) 2009-03-06T18:58:11Z 2026-03-27T01:40:36Z Epoxide hydrolase 1 (P07099) Cytochrome P450 2E1 (P05181) Glutathione S-transferase Mu 1 (P09488) Glutathione S-transferase theta-1 (P30711) (L990, A294, A295) http://en.wikipedia.org/wiki/1,3-butadiene C16450 39478 BUTADIENE C031763 1,3-Butadiene 204 true Epoxide hydrolase 1 (P07099) Cytochrome P450 2E1 (P05181) Glutathione S-transferase Mu 1 (P09488) Glutathione S-transferase theta-1 (P30711) (L990, A294, A295) C=CC=C C4H6 InChI=1S/C4H6/c1-3-4-2/h3-4H,1-2H2 KAKZBPTYRLMSJV-UHFFFAOYSA-N 54.0904 54.046950192 Exogenous Liquid 1.99 HMDB41792 CHEMBL537970 7557 CHEM000143 DTXSID3020203 NS00007558 0.0 20.2944 6.6958421237309125 1 0 0 0 0 1.94 -1.74 9.79e-01 g/l