557358
2-Methyl-1,5-hexadiene
97%
Synonym(s):
2-Methyldiallyl
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About This Item
Linear Formula:
CH2=CHCH2CH2C(CH3)=CH2
CAS Number:
Molecular Weight:
96.17
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
vapor density
>1 (vs air)
Assay
97%
refractive index
n20/D 1.417 (lit.)
n20/D 1.4170 (lit.)
bp
92 °C (lit.)
density
0.712 g/mL at 25 °C (lit.)
functional group
allyl
SMILES string
CC(=C)CCC=C
InChI
1S/C7H12/c1-4-5-6-7(2)3/h4H,1-2,5-6H2,3H3
InChI key
SLQMKNPIYMOEGB-UHFFFAOYSA-N
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General description
2-Methyl-1,5-hexadiene on mercury-photosensitized irradiation, undergoes internal cycloaddition to afford 1-methylbicyclo[2.1.1]hexane (as major product). High-temperature pyrolysis of 2-methyl-1,5-hexadiene affords 1,5-hexadiene and 2,5-dimethyl-1,5-hexadiene. 2-Methyl-1,5-hexadiene undergoes stereoselective and regioselective reaction with dialkylaluminum chloride (Et2AlCl) and titanium alkoxide [Ti(OPr-i)4, a catalyst] followed by oxidation to afford the corresponding five-membered 3-alkylcycloalkyl methanol. 2-Methyl-1,5-hexadiene is formed as a major product during the condensation reaction between allyl chloride and methallyl chloride in the presence of magnesium.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 1A - Flam. Liq. 2 - Muta. 1B - STOT RE 2
Target Organs
Blood
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
10.4 °F - closed cup
Flash Point(C)
-12 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Vapor-phase thermolyses of 3-hydroxy-1, 5-hexadienes. II. Effects of methyl substitution.
Negishi EI, et al.
Journal of the American Chemical Society, 116(18), 8404-8405 (1994)
Olefins and Diolefins from Allylic Chlorides.
Henne AL, et al.
Journal of the American Chemical Society, 63(12), 3474-3476 (1941)
Mercury (3P1) photosensitized internal cycloaddition reactions in 1, 4-, 1, 5-, and 1, 6-dienes.
Srinivasan R and Carlough KH.
Journal of the American Chemical Society, 89(19), 4932-4936 (1967)
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