Conditions | Yield |
---|---|
With ferric nitrate; barium(II) chloride at 90℃; for 0.666667h; | 100% |
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.8h; | 100% |
With ruthenium trichloride; iodobenzene; potassium peroxymonosulfate In water; acetonitrile at 20℃; for 0.8h; Inert atmosphere; | 100% |
adamantane
A
2-Adamantanone
B
1-adamanthanol
C
1,3-adamantandiol
Conditions | Yield |
---|---|
With methyltrifluoromethyldioxirane In dichloromethane at -22℃; for 0.0166667h; | A n/a B n/a C 86% |
With 6-chloro-4-trifluoromethyl-1,2,3-benzoxathiazine-2,2-dioxide; urea hydrogen peroxide adduct; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 1,2-dichloro-ethane at 22℃; for 95h; | A n/a B 80% C 5% |
With tetrabutylammomium bromide; oxygen; N-hydroxyphthalimide In water at 80℃; under 760 Torr; for 6h; Product distribution; further additives, solvents; | A 12% B 60% C 23% |
Conditions | Yield |
---|---|
With pyridine; bis(acetylacetonate)oxovanadium; dihydrogen peroxide; Hexafluoroacetone In water at 60℃; Catalytic behavior; Temperature; Reagent/catalyst; | A 70% B n/a |
With tetrachloromethane; tetrabutylammomium bromide; water; molybdenum hexacarbonyl at 140℃; for 13h; Inert atmosphere; | A 66% B 34% |
With sodium periodate; ruthenium(IV) oxide In tetrachloromethane; water; acetonitrile at 20℃; for 19h; | A 1.6% B 62% |
Conditions | Yield |
---|---|
With tris[trinitratocerium(IV)] paraperiodate at 90℃; for 0.25h; | 95% |
With ruthenium trichloride; toluene-4-sulfonic acid In N,N-dimethyl acetamide; water at 120℃; under 760.051 Torr; for 14h; Inert atmosphere; Green chemistry; | 95% |
With L-alanin; silica gel; chlorochromic acid In dichloromethane at 20℃; for 9h; | 90% |
Multi-step reaction with 2 steps 1: 1.) sodium nitrite, AcOH, 2.) NaBH4 / 1.) CH2Cl2, room temperature, 4 h, 2.) EtOH, room temperature, 1 h 2: 33 percent / 1 h / 160 °C View Scheme | |
With gold(III) tribromide; dimethylglyoxal In ethanol; water at 20℃; for 15h; pH=7; | 100 %Spectr. |
Conditions | Yield |
---|---|
With samarium(III) nitrate hexahydrate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | A n/a B 60% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution; | A n/a B 97% C n/a |
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Yields of byproduct given; | A n/a B 97% C n/a |
With ammonium cerium(IV) nitrate; oxygen In acetonitrile for 5h; Ambient temperature; Irradiation; | A 5% B 85% C 5% |
adamantane
A
2-Adamantanone
B
1-adamanthanol
C
1-adamantanol
D
1,3-adamantandiol
Conditions | Yield |
---|---|
With BaFeO(2.8-x); oxygen at 89.84℃; under 750.075 Torr; for 96h; Catalytic behavior; | A 5% B 48% C 3% D 11% |
With oxygen; propionic acid; bis(acetylacetonate)oxovanadium at 120℃; under 760.051 Torr; for 6h; Product distribution / selectivity; | A 5.5% B 31.6% C 3.9% D 7.9% |
With methanesulfonic acid; oxygen; propionic acid; bis(acetylacetonate)oxovanadium at 100℃; under 760.051 Torr; for 6h; Product distribution / selectivity; | A 4.2% B 25.1% C 3.9% D 2.4% |
adamantane-2-thione
2-Adamantanone
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate In dichloromethane for 0.5h; Ambient temperature; | 94% |
With ozone In diethyl ether at -70℃; | 90% |
With clay supported cupric nitrate In dichloromethane Ambient temperature; | 68% |
spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]
B
2-Adamantanone
Conditions | Yield |
---|---|
With triethylamine In cyclohexane at 0 - 20℃; for 3h; | A 11% B n/a |
A
spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]
B
2-Adamantanone
Conditions | Yield |
---|---|
With N-Bromosuccinimide In cyclohexane at 80℃; for 3h; | A 8% B n/a |
2-Adamantanone
Conditions | Yield |
---|---|
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; | 84% |
A
2-Adamantanone
B
1-(3,5-bis(trifluoromethyl)phenyl)-3,5-dimethylpyrazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 80% B 91% |
2-Adamantanone
Conditions | Yield |
---|---|
With nitric acid; arsenic(III) trioxide In dichloromethane at 0 - 5℃; | 96% |
Stage #1: 2,2-propanediyldimercaptoadamantane With chloro-trimethyl-silane; sodium iodide In acetonitrile at 60℃; for 24h; Stage #2: With water In acetonitrile for 0.0833333h; | 88% |
acetylacetone
A
2-Adamantanone
B
1-(4-bromophenyl)-3,5-dimethylpyrazole hydrochloride
Conditions | Yield |
---|---|
Stage #1: C16H19BrN2; acetylacetone With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere; | A 86% B 86% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 92% B 91% |
C16H20N2
acetylacetone
A
2-Adamantanone
B
3,5-dimethyl-1-phenyl-1H-pyrazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Reagent/catalyst; Inert atmosphere; | A 92% B 95% |
adamantane
A
2-Adamantanone
B
4-oxohomoadamantan-5-one
C
1-adamanthanol
D
1-adamantanol
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; ammonium cerium (IV) nitrate; oxygen In 1,2-dichloro-ethane at 40℃; for 24h; |
Conditions | Yield |
---|---|
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h; | 98% |
With potassium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity; | 87% |
With lithium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity; | 87% |
2-(methoxymethylene)adamantane
A
2-Adamantanone
B
tricyclo<3.3.1.13,7>decane-2-spiro-3'-(4'-methoxy-1',2'-dioxetane)
Conditions | Yield |
---|---|
With trimethylsilyl cyanide; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -70℃; Irradiation; | A 22% B 30% C 35% |
adamantylidene-adamantane
A
2-Adamantanone
B
bisadamantylidene epoxide
Conditions | Yield |
---|---|
With oxygen In dichloromethane for 16h; Irradiation; | A 30% B 9% |
With oxygen In dichloromethane Irradiation; | |
With chromyl nitrate In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide at -78℃; for 1h; Title compound not separated from byproducts; | A 3 % Chromat. B 92 % Chromat. |
3.3.1.13,7.tricyclo 2-decane 2'-spiro(1',3'-dithiolanne)
2-Adamantanone
Conditions | Yield |
---|---|
With (CH3)3CI; dimethyl sulfoxide for 12h; | 85% |
With trimethylsilyl bromide; dimethyl sulfoxide In tetrachloromethane at 75 - 80℃; for 28h; | 75% |
bis(adamantylidene)methane
2-Adamantanone
Conditions | Yield |
---|---|
With oxygen; methylene blue In dichloromethane at 15℃; for 7.5h; Irradiation; | 87% |
2-Adamantanone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 8h; | 62% |
acetylacetone
A
2-Adamantanone
B
1-(4-methylphenyl)-3,5-dimethyl-1H-pyrazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 80% B 84% |
acetylacetone
A
2-Adamantanone
B
1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 90% B 84% |
acetylacetone
A
2-Adamantanone
B
2-(3,5-dimethylpyrazol-1-yl)-N,N-diethyl-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 87% B 84% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 82% B 86% |
acetylacetone
benzylmagnesium chloride
spiro[adamantane-2,3'-diazirine]
A
2-Adamantanone
B
1-benzyl-3,5-dimethyl-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: benzylmagnesium chloride; spiro[adamantane-2,3'-diazirine] In diethyl ether at 0℃; for 2h; Inert atmosphere; Stage #2: acetylacetone With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere; | A 84% B 100% |
adamantane
3,3-dimethyldioxirane
A
2-Adamantanone
B
1-adamanthanol
C
1-adamantanol
Conditions | Yield |
---|---|
In acetone at 22℃; for 18h; protected from light; | A n/a B 87% C n/a |
2-adamantylidene-N-tert-butylaziridine
A
2-Adamantanone
B
N-methylene-tert-butylamine
C
N-t-butylaziridinone
Conditions | Yield |
---|---|
With oxygen; methylene blue In chloroform-d1 at 15℃; for 1h; Irradiation; | A 100% B 16 % Chromat. C n/a |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; | 100% |
Stage #1: 2-Adamantanone; ethyllithium In tetrahydrofuran; diethyl ether; benzene at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water; benzene Inert atmosphere; | 94% |
In tetrahydrofuran; benzene at 0℃; | 94% |
In diethyl ether; benzene |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane Ambient temperature; | 100% |
With titanium tetrachloride In dichloromethane at 20℃; for 16h; Schmidt insertion; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; xylene 1.) 18 h, room temp., 2.) 1 h, 70 deg C; | 100% |
In tetrahydrofuran; xylene a) RT, 18 h, b) 70 deg C, 1 h; | 5.30 g |
Conditions | Yield |
---|---|
With potassium hydroxide In isopropyl alcohol for 1h; Reflux; | 100% |
With sodium hydroxide In isopropyl alcohol for 1h; Heating; | 85% |
With potassium tert-butylate In 1,2-dimethoxyethane for 18h; Heating; | 85% |
With sodium hydride Corey-Chaykovsky epoxidation; | 65% |
Epoxidation; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; | 100% |
2-Adamantanone
4-oxohomoadamantan-5-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid; scandium tris(trifluoromethanesulfonate) In dichloromethane for 0.333333h; Ambient temperature; | 100% |
With oxone; silica gel In dichloromethane at 20℃; for 1h; Baeyer-Villiger oxidation; | 99% |
With bis(2-phenyltrifluoromethanesulfonate)diselenide; dihydrogen peroxide In dichloromethane at 20℃; for 17h; Baeyer-Villiger oxidation; | 99% |
Conditions | Yield |
---|---|
With lithium vanadium(I) dihydride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | 100% |
With manganese(III) (Z)-2,2,6,6-tetramethyl-5-oxohept-3-en-3-olate; phenylsilane; oxygen In 1,2-dichloro-ethane; isopropyl alcohol at 23℃; under 760 Torr; | 99% |
With ethanol; (ethylenebis(bicyclohexylphosphane))Ni(cis,cis-1,5-cyclooctadiene) In neat (no solvent) at 130℃; for 36h; Catalytic behavior; | 99% |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol at 60℃; for 2h; | 100% |
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; | 95% |
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 1h; Heating; | 86% |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide for 10h; Reflux; | 100% |
With potassium hydroxide for 12h; Heating; | 86% |
With perhydrodibenzo-18-crown-6; potassium hydroxide Heating; | 80% |
With potassium hydroxide In dimethyl sulfoxide for 10h; Reflux; |
Conditions | Yield |
---|---|
With piperidine In benzene for 36h; Heating; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 2-Adamantanone In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.; | 100% |
2-Adamantanone
1,1-dilithio-2,3,4,5-tetraphenyl-1-silacyclopentadiene
Conditions | Yield |
---|---|
In toluene at -78 - 20℃; | 100% |
2-Adamantanone
adamantylideneacetic acid methyl ester
Conditions | Yield |
---|---|
With sodium methylate In methanol; water | 100% |
2-Adamantanone
1,1'-biphenyl-2,2'-diamine
N,N'-di(2-adamantyl) 1,1'-biphenyl-2,2'-diamine
Conditions | Yield |
---|---|
Stage #1: 2-Adamantanone; 1,1'-biphenyl-2,2'-diamine With toluene-4-sulfonic acid In toluene for 72h; Heating / reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 50℃; for 2h; Stage #3: With water; ammonium chloride In tetrahydrofuran; toluene | 100% |
With sodium tetrahydroborate; sulfuric acid In tetrahydrofuran; water at 20℃; for 5h; | 74% |
2-Adamantanone
2-n-butyladamantanol-2
Conditions | Yield |
---|---|
Stage #1: 2-Adamantanone With n-butyllithium In diethyl ether at -78℃; for 0.166667h; Stage #2: With methanol | 100% |
Conditions | Yield |
---|---|
With acetic acid In methanol for 1h; Reflux; | 100% |
2-Adamantanone
toluene-4-sulfonic acid hydrazide
N'-(adamantan-2-ylidene)-4-methylbenzenesulfonohydrazide
Conditions | Yield |
---|---|
In methanol at 20℃; Schlenk technique; | 100% |
In methanol at 70℃; for 2h; Schlenk technique; |
Conditions | Yield |
---|---|
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere; | 100% |
IUPAC Name: Adamantan-2-one
Synonyms of 2-Adamantanone (CAS NO.700-58-3): 2-Adamantone ; 2-Oxoadamantane ; Adamantanone ; Tricyclo(3.3.1.13,7)decan-2-one ; Tricyclo(3.3.1.13,7)decanone (9CI)
CAS NO: 700-58-3
Molecular Formula: C10H14O
Molecular Weight: 150.22
Molecular Structure:
EINECS: 211-847-2
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 17.07 Å2
Index of Refraction: 1.535
Molar Refractivity: 42.35 cm3
Molar Volume: 135.9 cm3
Surface Tension: 38.6 dyne/cm
Density: 1.105 g/cm3
Flash Point: 95.7 °C
Enthalpy of Vaporization: 48.39 kJ/mol
Boiling Point: 246.7 °C at 760 mmHg
Vapour Pressure: 0.0267 mmHg at 25°C
Melting Point: 256-258 °C (subl.)(lit.)
Solubility: methanol: 0.1 g/mL, clear
Appearance: white to off-white crystalline powder
Product Categories of 2-Adamantanone (CAS NO.700-58-3): Adamantane Derivative;FINE Chemical & INTERMEDIATES;Adamantane derivatives;Adamantanes;Ring Systems;C10;Carbonyl Compounds;Ketones
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 780mg/kg (780mg/kg) | Pharmaceutical Chemistry Journal Vol. 10, Pg. 454, 1976. |
Safety Information about 2-Adamantanone (CAS NO.700-58-3):
Hazard Codes: Xi
Risk Statements: 52-36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
R52: Harmful to aquatic organisms.
Safety Statements: 22-24/25-36-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
WGK Germany: 2
RTECS: AU5018000
Hazard Note: Irritant
HS Code: 29142900
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.
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