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251356

Sigma-Aldrich

Methylenecyclopentane

97%

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About This Item

Linear Formula:
C5H8(=CH2)
CAS Number:
Molecular Weight:
82.14
Beilstein/REAXYS Number:
1847501
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

97%

refractive index

n20/D 1.435 (lit.)

bp

75-76 °C (lit.)

density

0.781 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C=C1CCCC1

InChI

1S/C6H10/c1-6-4-2-3-5-6/h1-5H2

InChI key

NFJPEKRRHIYYES-UHFFFAOYSA-N

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General description

Hydration rate of methylenecyclopentane has been measured spectrophotometrically in aqueous perchloric acid. Trost′s palladium-mediated methylenecyclopentane annelation to the nitroalkene yields methylenecyclopentane derivative.

Application

Methylenecyclopentane has been used in total synthesis of (±)-cephalotaxin.

pictograms

FlameHealth hazard

signalword

Danger

hcodes

Hazard Classifications

Asp. Tox. 1 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-0.4 °F - closed cup

flash_point_c

-18 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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The total synthesis of cephalotaxine.
J Auerbach et al.
Journal of the American Chemical Society, 94(20), 7172-7173 (1972-10-04)
COMPARISON OF THE TRANSITION-STATE ENERGIES OF ACID-CATALYZED HYDRATIONS OF SOME 1-METHYLCYCLOALKENES AND METHYLENECYCLOALKANES.
Lajunen M and Himottu M.
Acta Chemica Scandinavica, 41(5), 252-258 (1987)

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