Skip to Content
Merck
All Photos(3)

Key Documents

146048

Sigma-Aldrich

2-Adamantanone

ReagentPlus®, 99%

Synonym(s):

2-Oxoadamantane, Tricyclo[3.3.1.13,7]decanone (9CI)

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
Beilstein:
1210235
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

Assay

99%

form

solid

mp

256-258 °C (subl.) (lit.)

functional group

ketone

SMILES string

O=C1C2CC3CC(C2)CC1C3

InChI

1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2/t6-,7+,8-,9+

InChI key

IYKFYARMMIESOX-SPJNRGJMSA-N

Looking for similar products? Visit Product Comparison Guide

General description

2-Adamantanone on deprotonation in the gas phase affords the corresponding β-enolate anion. It reacts with 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole to yield 5-silafulvene.

Application

2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Matthew M Meyer et al.
The Journal of organic chemistry, 75(12), 4274-4279 (2010-05-26)
Deprotonation of 2-adamantanone (1) in the gas phase affords the corresponding beta-enolate anion. This ion was independently prepared by the fluoride-induced desilylation of 4-trimethylsilyl-2-adamantanone, and its reactivity and thermodynamic properties were measured (DeltaH degrees(acid) = 394.7 +/- 1.4, EA =
Sunil Sabbani et al.
Bioorganic & medicinal chemistry letters, 18(21), 5804-5808 (2008-10-11)
Dispiro N-Boc-protected 1,2,4-trioxane 2 was synthesised via Mo(acac)(2) catalysed perhydrolysis of N-Boc spirooxirane followed by condensation of the resulting beta-hydroperoxy alcohol 10 with 2-adamantanone. N-Boc 1,2,4-trioxane 2 was converted to the amine 1,2,4-trioxane hydrochloride salt 3 which was subsequently used
Roman Davydov et al.
Journal of the American Chemical Society, 127(5), 1403-1413 (2005-02-03)
EPR/ENDOR studies have been carried out on oxyferrous cytochrome P450cam one-electron cryoreduced by gamma-irradiation at 77 K in the absence of substrate and in the presence of a variety of substrates including its native hydroxylation substrate, camphor (a), and the
Solid-state and solution studies of a tetrameric capsule and its guests.
Darren W Johnson et al.
Angewandte Chemie (International ed. in English), 41(20), 3793-3796 (2002-10-19)
An adamantanone derivative that is an original modulator of redox processes in the cytochrome P-450 system can serve as an effective remedy against obliterating angiopathy of lower extremities.
I E Kovalev et al.
Doklady. Biochemistry and biophysics, 391, 201-203 (2003-10-09)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service