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295035 Sigma-Aldrich

1,3-Butadiene

≥99%

  • CAS Number 106-99-0

  • Linear Formula CH2=CHCH=CH2

  • Molecular Weight 54.09

  •  Beilstein/REAXYS Number 605258

  •  EC Number 203-450-8

  •  MDL number MFCD00008659

  •  PubChem Substance ID 24857754

  •  NACRES NA.22

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Properties

Related Categories Cancer Research, Carcinogens, Cell Biology, Chemical Synthesis, Specialty Gases,
Quality Level   100
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
SMILES string   C=CC=C
InChI   1S/C4H6/c1-3-4-2/h3-4H,1-2H2
InChI key   KAKZBPTYRLMSJV-UHFFFAOYSA-N

Description

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.

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.

Packaging

1 kg in Sure-Pac™

100, 400 g in Sure-Pac™

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.

Recommended products

Brass hose adapter Z146811 or brass body mini gas regulator Z513539 is recommended.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN1010 - class 2 - BUTADIENES, STABILIZED
WGK Germany 
WGK 3
Flash Point(F) 
-104.8 °F - closed cup
Flash Point(C) 
-76 °C - closed cup
Protocols & Articles

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 vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

GC Analysis of C1-C5 Hydrocarbons on Alumina Sulfate PLOT

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From our library of Articles, Sigma-Aldrich presents GC Analysis of Impurities in Propylene on Alumina Chloride PLOT
Keywords: Chromatography, Flame ionization detector, Gas chromatography, Sample preparations

US EPA Method TO-17: GC Analysis of Volatiles on Equity®-1 after Collection/Desorption using Carbotrap 300 Tube

From our library of Articles, Sigma-Aldrich presents US EPA Method TO-17: GC Analysis of Volatiles on Equity®-1 after Collection/Desorption using Carbotrap 300 Tube
Keywords: Chromatography, Gas chromatography

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Peer-Reviewed Papers
15

References

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