2-Adamantanone Chemical Properties

Melting point:

256-258 °C (subl.)(lit.)

Boiling point:

211.78°C (rough estimate)

Density 

0.8709 (rough estimate)

refractive index 

1.4993 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: 0.1 g/mL, clear

form 

Crystalline Powder

color 

White to off-white

BRN 

1210235

InChI

InChI=1S/C10H14O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-9H,1-5H2

InChIKey

IYKFYARMMIESOX-UHFFFAOYSA-N

SMILES

C12CC3CC(CC(C3)C1=O)C2

CAS DataBase Reference

700-58-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Adamantanone(700-58-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

52-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

2

RTECS 

AU5018000

Hazard Note 

Irritant

HS Code 

29142900

MSDS

• Language:English Provider:2-Adamantanone
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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2-Adamantanone Usage And Synthesis

Uses

2-Adamantanone has been used as a probe for the dimensions and characteristics for the substrate binding pocket of alcohol dehydrogenases.

synthesis

Dissolve the alcohol (0.25 mmol) in acetonitrile (3 mL). Add oxidant 1,3-dichloro-5,5-dimethylhydantoin (DCH, 0.148 g, 0.75 mmol) to the reaction mixture. Add the pre-catalyst MWCNT-{(CH2)3-CO- NH-TEMPO}n (0.075 g) to the reaction mixture. Sonic the resulting suspension (1 min.) using an ultrasonic bath. Stir the reaction mixture. Heat the reaction mixture at 50 °C for 30 minutes. Filter the reaction mixture. Add CH2Cl2 (10 mL) to the reaction mixture. Wash the organic phase with aqueous Na2S2O3 (10 %, 10 mL) and H2O (10 mL x 2). Dry the residue with Na2SO4. Remove the solvent under reduced pressure using a rotary evaporator to obtain the product.

Chemical Properties

white to off-white crystalline powder with camphor smell, soluble in methanol, ethanol, DMSO and other organic solvents, from synthesis.

Uses

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

Definition

ChEBI: Adamantanone is a member of adamantanones.

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.

Purification Methods

Purify 2-admantanone by repeated sublimation in vacuo. [Butler et al. J Chem Soc, Faraday Trans II 82 535 1986.]

2-Adamantanone(700-58-3)Related Product Information

• 5-CHLORO-2-ADAMANTANONE
• Adamantane
• Amantadine
• Decane
• 1-Adamantylacrylate
• 1,3,5-ADAMANTANETRIOL
• 1,3-Adamantanediol monoacrylate
• Altrenogest
• 4-Hydroxy-2-adamantone
• 5-HYDROXY-2-ADAMANTANONE
• 2-ADAMANTANONE-5-CARBOXYLIC ACID
• 2-ADAMANTANONE OXIME,Adamantanone-2-oxime,Adamantanone oxime
• 2-Adamantanone
• ADAMANTANONE, 2-(SG)
• 5-BROMO-2-ADAMANTANONE
• 2,6-ADAMANTANEDIONE
• RARECHEM AL BO 1792
• 4-OXOADAMANTANE-2-CARBONITRILE