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Sigma-Aldrich

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:
106-99-0
Molecular Weight:
54.09
Beilstein/REAXYS Number:
605258
EC Number:
203-450-8
MDL number:
MFCD00008659
UNSPSC Code:
12142100
PubChem Substance ID:
24857754
NACRES:
NA.22

vapor density

1.9 (15 °C, vs air)

Quality Level

100

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

SMILES string

C=CC=C

InChI

1S/C4H6/c1-3-4-2/h3-4H,1-2H2

InChI key

KAKZBPTYRLMSJV-UHFFFAOYSA-N

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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:
  • 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:

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

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Hazard Classifications

Flam. Gas 1A - Muta. 1B - Press. Gas Liquefied gas

Storage Class

2A - Gases

wgk_germany

WGK 3

flash_point_f

-104.8 °F - closed cup

flash_point_c

-76 °C - closed cup

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Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Palladium-Catalyzed Dimerization Disilylation of 1,3-Butadiene with Chlorosilanes.
Terao J, et al.
Organic Letters, 6(19), 3341-3344 (2004)
Carcinogenicity of 1,3-butadiene in C57BL/6 x C3H F1 mice at low exposure concentrations.
Melnick RL, et al.
Cancer Research, 50, 6592-6599 (1990)
Selective catalytic hydrodimerization of 1, 3-butadiene by palladium compounds dissolved in ionic liquids.
Dullius JEL, et al.
Organometallics, 17(5), 815-819 (1998)
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)
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
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Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product via a cyclic transition state, it is also referred to as a "cycloaddition".

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