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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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¥6,140
25 G
¥17,600
100 G
¥32,880

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5 G
¥6,140
25 G
¥17,600
100 G
¥32,880

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

¥6,140

Available to ship onApril 16, 2025Details

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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

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General description

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

Application

2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane[3] and (+/-)-1-(adamantan-2-yl)-2-propanamine[4].

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

146048-10KG:
146048-1G:
146048-BULK:
146048-5G:
146048-VAR:
146048-25G:
146048-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2527
MKCV2215
MKCR9911
MKCS4264
STBC6522V

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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
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 =
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)
A Corma et al.
Nature, 412(6845), 423-425 (2001-07-27)
The Baeyer-Villiger oxidation, first reported more than 100 years ago, has evolved into a versatile reaction widely used to convert ketones-readily available building blocks in organic chemistry-into more complex and valuable esters and lactones. Catalytic versions of the Baeyer-Villiger oxidation
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