295035

1,3-Butadiene

≥99%

• Synonym(s): Bivinyl, Vinylethylene, alpha,gamma-Butadiene
• 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

Properties

• 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

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.

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:

• Aldrich^® Sure/Pac^™ station for liquefied gases Z566446
• PTFE Sealing tape Z104388 or Z221880
• Brass hose adapter Z146811
• Aldrich^® mini gas regulator Z513539

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC

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

Safety Information

• pictograms: GHS02,GHS04,GHS08
• signalword: Danger
• hcodes: H220,H280,H340
• pcodes: P202 - P210 - P280 - P308 + P313 - P377 - P410 + P403
• 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
• ppe: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)