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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:
5597-27-3
Molecular Weight:
122.16
EC Number:
227-009-4
MDL number:
MFCD00151643
UNSPSC Code:
12352100
PubChem Substance ID:
24896927

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
GHS02

Signal Word

Warning

Hazard Statements

H226

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)
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
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)

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