All Photos(3)

146048

Sigma-Aldrich

2-Adamantanone

ReagentPlus®, 99%

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

product line

ReagentPlus®

Quality Level

assay

99%

mp

256-258 °C (subl.) (lit.)

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

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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.

Packaging

5, 25, 100 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Storage Class Code

13 - Non 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

Certificate of Analysis

Certificate of Origin

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
Yulan Chen et al.
Nature chemistry, 4(7), 559-562 (2012-06-22)
Nature uses mechanochemical transduction processes to achieve diverse and vital functions, such as hearing, cellular adhesion and gating of ion channels. One fascinating example of biological mechanotransduction is the emission of light on mechanical stimulation. However, molecular-level transduction of force
Hassen Jaafar et al.
Dalton transactions (Cambridge, England : 2003), 40(1), 92-106 (2010-11-19)
We report that the oxygen sensitivity of some Fe(II) complexes with tripodal ligands can be used, with benefit, in the oxidation of cyclohexane under mild conditions. Depending on the solvent, two very different reaction pathways are involved, which share the
Irina S Toulokhonova et al.
Journal of the American Chemical Society, 126(17), 5336-5337 (2004-04-29)
Reaction of 1,1-dilithio-1-sila-2,3,4,5-tetraphenylsilole with 2-adamantanone produces a 5-silafulvene. This represents a new method for synthesis of silenes, leading to the first example of a silapentafulvene.

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