146048

Sigma-Aldrich

2-Adamantanone

ReagentPlus®, 99%

Empirical Formula (Hill Notation):
C10H14O
CAS Number:
Molecular Weight:
150.22
Beilstein/REAXYS Number:
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

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
W T Nolan et al.
International journal of radiation biology and related studies in physics, chemistry, and medicine, 39(2), 195-205 (1981-02-01)
The repair of sublethal radiation damage (SLD) in Chinese hamster (V79) cells was investigated as a function of temperature in the presence and absence of the membrane lipid perturbers, butylated hydroxytoluene (BHT) or adamantanone, which decrease the viscosity of 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)

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