3-methylbuta-1,2-diene

• ChemBase ID: 151740
• Molecular Formular: C5H8
• Molecular Mass: 68.11702
• Monoisotopic Mass: 68.06260026
• SMILES: CC(=C=C)C
• Canonical SMILES: C=C=C(C)C
• InChI: InChI=1S/C5H8/c1-4-5(2)3/h1H2,2-3H3
• InChIKey: PAKGDPSCXSUALC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methylbuta-1,2-diene
• IUPAC Traditional name: 3-methyl-1,2-butadiene
• Synonyms: 1,1-Dimethylallene; 3-Methyl-1,2-butadiene; 3,3-Dimethylallene; 1,1-二甲基丙二烯; 3-甲基-1,2-丁二烯

Database IDs

• CAS Number: 598-25-4
• EC Number: 209-926-1
• MDL Number: MFCD00008896
• Beilstein Number: 1697090
• PubChem SID: 162245890; 24846867; 24884434
• PubChem CID: 11714

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.9737272
• LogD (pH = 7.4): 1.9737272
• Log P: 1.9737272
• Molar Refractivity: 24.213 cm^3
• Polarizability: 9.2004 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -114°C; -148 °C(lit.)
• Boiling Point: 40-41 °C(lit.); 40-41°C
• Flash Point: 10.4 °F; -12 °C; -12°C(10°F)
• Density: 0.694; 0.694 g/mL at 25 °C(lit.)
• Refractive Index: 1.4190; n20/D 1.419(lit.); n20/D 1.420
• Vapor Pressure: 6.87 psi ( 20 °C)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 3295; UN3295
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36/37/38-65
• Safety Statements: 16-26-36-62; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H315-H319-H335
• GHS Precautionary statements: P210-P261-P301 + P310-P305 + P351 + P338-P331; P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 3295 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 97%; 97+%
• Grade: purum
• Linear Formula: (CH3)2C=C=CH2

DETAILS

Sigma Aldrich - 110930

Packaging
1 g in ampule

Sigma Aldrich - 65960

Other Notes
Used in the chiral isoprenylation of aldehydes1

REFERENCES

• Hydroboration with (+)-diisopinocampheylborane gives 3,3-dimethylallyldiisopinocampheylborane, which has been used in the chiral isoprenylation of aldehyde; the reaction was used in the synthesis of artemisia alcohol in 96% ee: Tetrahedron Lett., 25, 1215 (1984).