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M46055

Sigma-Aldrich

3-Methylene-2-norbornanone

97%

Synonym(s):

3-methylene-bicyclo[2,2,1]heptan-2-one

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About This Item

Empirical Formula (Hill Notation):
C8H10O
CAS Number:
Molecular Weight:
122.16
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

Assay

97%

refractive index

n20/D 1.493 (lit.)

bp

69-71 °C/11 mmHg (lit.)

density

0.997 g/mL at 25 °C (lit.)

SMILES string

C=C1[C@@H]2CC[C@@H](C2)C1=O

InChI

1S/C8H10O/c1-5-6-2-3-7(4-6)8(5)9/h6-7H,1-4H2/t6-,7+/m1/s1

InChI key

FNOOZJAPZFHNCW-RQJHMYQMSA-N

Application

3-Methylene-2-norbornanone can be used as a reactant to prepare:
  • 3-(2-(4-methoxyphenyl)-2-oxoethyl)bicyclo[2.2.1]heptan-2-one by reacting with 4-anisaldehyde in the presence of tetrabutylammonium decatungstate (TBADT) photocatalyst.
  • 2-Aryl-3-methylene-endo-norbornanols by treating with corresponding aryl lithium reagents.

Pictograms

Flame

Signal Word

Warning

Hazard Statements

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

131.0 °F - closed cup

Flash Point(C)

55 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Structural effects in solvolytic reactions. 32. Effect of increasing electron demand on the rates of solvolysis of 2-aryl-3-methylene-2-norbornyl p-nitrobenzoates. High exo/endo rate and product ratios for tertiary derivatives of the accepted classical 3-methylene-2-norbornyl system
Brown HC and Rao C G
The Journal of Organic Chemistry, 44(20), 3536-3540 (1979)
Benzoyl radicals from (hetero) aromatic aldehydes. Decatungstate photocatalyzed synthesis of substituted aromatic ketones
Ravelli D, et al.
Organic & Biomolecular Chemistry, 8(18), 4158-4164 (2010)
Masayuki Takaishi et al.
The journal of physiological sciences : JPS, 64(1), 47-57 (2013-10-15)
TRPA1, one of the transient receptor potential channels, has been reported to be involved in nociception and inflammatory pain, suggesting that this molecule could be a promising target for the development of analgesic agents. We screened several monoterpene analogs of

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