5-Hydroxyadamantan-2-one Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

296.5±33.0 °C(Predicted)

Density 

1.301±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO, Methanol

pka

14.69±0.20(Predicted)

form 

Crystalline Powder

color 

White to off-white

InChI

InChI=1S/C10H14O2/c11-9-7-1-6-2-8(9)5-10(12,3-6)4-7/h6-8,12H,1-5H2

InChIKey

TZBDEVBNMSLVKT-RIKBPLFRSA-N

SMILES

C12CC3(O)CC(CC(C3)C1=O)C2

CAS DataBase Reference

20098-14-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36/37/39-27-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29144000

MSDS

• Language:English Provider:SigmaAldrich

5-Hydroxyadamantan-2-one Usage And Synthesis

Description

5-Hydroxy-2-adamantanone (5-hydroxyadamantan-2-one) is a versatile starting material for synthesising various 2,5- or 1,4-disubstituted adamantanes. Chemical methods for synthesizing 5-hydroxy-2-adamantanone include disproportionation of 2-hydroxyadamantane and oxidation of 2-adamantanone. A synthetic approach to produce 5-hydroxy-2-adamantanone using P450cam (CYP101A1; a camphor monooxygenase) coupled with NADH regeneration as an oxidation biocatalyst has been reported[1].

Chemical Properties

White crystal or crystalline powder

Uses

anthelmintic

Uses

5-Hydroxy-2-adamantanone may be used in the following studies:

• As a model compound to investigate the application of lanthanide NMR shift reagents for the analysis of disubstituted derivative of adamantane.
• As a starting material for the synthesis of E-2-amino-5-hydroxyadamantane.
• As a starting material for the synthesis of 4-(triphenylsilyloxy)adamantan-1-ol.

Definition

ChEBI: Idramantone is a member of adamantanones.

brand name

INDICLOR (Nycomed Amersham).

General Description

5-Hydroxy-2-adamantanone is a disubstituted derivative of adamantane. The biocatalyzed synthesis of 5-hydroxy-2-adamantanone from 2-adamantanone has been investigated.

References

[1] Toshiki Furuya . “Biocatalytic production of 5-hydroxy-2-adamantanone by P450cam coupled with NADH regeneration.” Journal of Molecular Catalysis B-enzymatic 94 (2013): Pages 111-118.

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