295035
1,3-Butadiene
≥99%
Synonym(s):
Bivinyl, Vinylethylene, alpha,gamma-Butadiene
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About This Item
Linear Formula:
CH2=CHCH=CH2
CAS Number:
Molecular Weight:
54.09
UNSPSC Code:
12142100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
203-450-8
Beilstein/REAXYS Number:
605258
MDL number:
Assay:
≥99%
InChI key
KAKZBPTYRLMSJV-UHFFFAOYSA-N
InChI
1S/C4H6/c1-3-4-2/h3-4H,1-2H2
SMILES string
C=CC=C
vapor density
1.9 (15 °C, vs air)
vapor pressure
1863 mmHg ( 21 °C)
assay
≥99%
autoignition temp.
788 °F
contains
p-tert-butylcatechol as inhibitor
expl. lim.
12 %
bp
−4.5 °C (lit.)
mp
−109 °C (lit.)
solubility
water: soluble 0.5 g/L at 20 °C
density
0.62 g/mL at 20 °C (lit.)
storage temp.
2-8°C
Quality Level
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General description
1,3-Butadiene (BD) is a simplest conjugated diene. It is a colorless gas that turns to liquid easily. The vapor phase conversion of ethanol in the presence of Cr-Ba/MCM-41 (mesoporous silica molecular sieve) catalyst reported a yield of 25% of BD. It is also formed as a coproduct of ethylene production. Mechanism of Diels-Alder reaction of 1,3-butadiene with ethylene has been investigated.
May contain up to 4% dimer impurity.
Application
1,3-Butadiene can undergo a four-component coupling reaction with aryl Grignard reagents, and alkyl fluorides in the presence of nickel catalyst to form 1,6-octadiene carbon compound substituted with alkyl and aryl groups at the 3- and 8-positions.
1,3-Butadiene is a useful diene for Diels Alder reaction.
It may be used in the synthesis of the following:
It may be used in the synthesis of the following:
- 1-Silyl-substituted 1,3-butadienes, by [RuHCl(CO)(PCy3)2]-catalyzed silylative coupling of terminal (E)-1,3-dienes with vinylsilanes.
- Synthetic rubber and thermoplastic resins.
- Disilylated dimers by reacting with chlorosilanes.
- Octa-2,7-dien-1-ol via palladium catalyzed-hydrodimerization.
Biochem/physiol Actions
1,3-Butadiene has been reported to induce hemangiosarcomas of the heart, malignant lymphomas, alveolar-bronchiolar neoplasms, squamous cell neoplasms of the forestomach in males and female mice. It also induced acinar cell carcinomas of the mammary gland, granulosa cell neoplasms of the ovary, and hepatocellular neoplasms in female mice. Carcinogenicity induced by inhaled 1,3-butadiene has been investigated in C57BL/6 x C3H F1 mice.
Environmental carcinogen. Induces cardiac hemangiosarcomas in mice.
Packaging
Supplied in a Sure/Pac™ cylinder and has a brass needle valve with a male 1/4" NPTF outlet thread installed. Before using the cylinder, ensure that the valve is closed, then remove the galvanized steel hex cap that seals the outlet valve.
Compatible with the following:
Compatible with the following:
Legal Information
Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC
signalword
Danger
hcodes
Hazard Classifications
Flam. Gas 1A - Muta. 1B - Press. Gas Liquefied gas
Storage Class
2A - Gases
wgk
WGK 3
flash_point_f
-104.8 °F - closed cup
flash_point_c
-76 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)
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J E Huff et al.
Science (New York, N.Y.), 227(4686), 548-549 (1985-02-01)
Groups of 50 male and 50 female B6C3F1 mice were exposed 6 hours per day, 5 days per week, for 60 to 61 weeks to air containing 0, 625, or 1250 parts per million 1,3-butadiene. These concentrations are somewhat below
Nickel-catalyzed coupling reaction of alkyl halides with aryl Grignard reagents in the presence of 1, 3-butadiene: Mechanistic studies of four-component coupling and competing cross-coupling reactions.
Iwasaki T, et al.
Chemical Science (2018)
Useful diene for the Diels-Alder reaction.
Danishefsky S and Kitahara T.
Journal of the American Chemical Society, 96(25), 7807-7808 (1974)
Selective catalytic hydrodimerization of 1, 3-butadiene by palladium compounds dissolved in ionic liquids.
Dullius JEL, et al.
Organometallics, 17(5), 815-819 (1998)
Palladium-Catalyzed Dimerization Disilylation of 1,3-Butadiene with Chlorosilanes.
Terao J, et al.
Organic Letters, 6(19), 3341-3344 (2004)
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