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146048

Sigma-Aldrich

2-Adamantanone

ReagentPlus®, 99%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
700-58-3
Molecular Weight:
150.22
Beilstein:
1210235
EC Number:
211-847-2
MDL number:
MFCD00074737
UNSPSC Code:
12352100
PubChem Substance ID:
24848757
NACRES:
NA.22

product line

ReagentPlus®

Assay

99%

form

solid

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.

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

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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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
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.
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)
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
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