2-Adamantanone

2-Adamantanone
  • CAS No.:700-58-3
Other grades of this product :
2-Adamantanone Basic information
Uses synthesis
Product Name:2-Adamantanone
Synonyms:2-ADAMANTANONE;2-ADAMANTONE;Adamantanone;tricyclo(3.3.1.1(sup3,7))decanone;OTAVA-BB BB0110864325;tricyclo[3.3.1.1(3,7)]decane-2-one;TRICYCLO[3,3,1,1(3,7)]DECANONE;AKOS BC-0654
CAS:700-58-3
MF:C10H14O
MW:150.22
EINECS:211-847-2
Product Categories:FINE Chemical & INTERMEDIATES;Adamantane Derivative;Adamantane derivatives;Adamantanes;Ring Systems;C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
Mol File:700-58-3.mol
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
InChIKeyIYKFYARMMIESOX-UHFFFAOYSA-N
CAS DataBase Reference700-58-3(CAS DataBase Reference)
NIST Chemistry Reference2-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 Information
ProviderLanguage
2-Adamantanone English
ACROS English
SigmaAldrich English
ALFA English
2-Adamantanone Usage And Synthesis
Uses2-Adamantanone has been used as a probe for the dimensions and characteristics for the substrate binding pocket of alcohol dehydrogenases.
synthesisDissolve 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 Propertieswhite to off-white crystalline powder with camphor smell, soluble in methanol, ethanol, DMSO and other organic solvents, from synthesis.
Uses2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.
General Description2-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 MethodsPurify 2-admantanone by repeated sublimation in vacuo. [Butler et al. J Chem Soc, Faraday Trans II 82 535 1986.]
2-Adamantanone Preparation Products And Raw materials
Raw materials3,3-Dimethyl-2-oxobutyric acid
Preparation Products2-Ethyl-2-adamantanol-->2-Methyl-2-adamantanol-->5-Hydroxyadamantan-2-one-->2-Adamantanol-->2-Isopropyl-2-adamantanol

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