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| CAS No.: | 700-58-3 |
|---|---|
| Name: | 2-Adamantanone |
| Molecular Structure: | |
|
|
|
| Formula: | C10H14O |
| Molecular Weight: | 150.221 |
| Synonyms: | Tricyclo[3.3.1.13,7]decanone;2-Oxoadamantane;tricyclo[3.3.1.1(3,7)]decan-2-one;2-Adamantantanone;Tricyclo(3,3,1,13,7)decanone;adamantan-2-one;Adamantanone;Tricyclo(3.3.1.13,7)decanone (9CI);Tricyclo(3.3.1.1(sup 3,7))decanone;Tricyclo(3.3.1.13,7)decan-2-one; |
| EINECS: | 211-847-2 |
| Density: | 1.105 g/cm3 |
| Melting Point: | 256-258 °C (subl.)(lit.) |
| Boiling Point: | 246.7 °C at 760 mmHg |
| Flash Point: | 95.7 °C |
| Solubility: | methanol: 0.1 g/mL, clear |
| Appearance: | white to off-white crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 52-36/37/38 |
| Safety: | 22-24/25-36-26 |
| PSA: | 17.07000 |
| LogP: | 2.01160 |
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| 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% |
| 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% |
- 281-23-2
adamantane
A
- 700-58-3
2-Adamantanone
B
- 768-95-6
1-adamanthanol
C
- 700-57-2
1-adamantanol
D
- 5001-18-3
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% |
- 23695-65-0
adamantane-2-thione
- 700-58-3
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% |
- 518050-74-3
spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]
B
- 700-58-3
2-Adamantanone
| Conditions | Yield |
|---|---|
| With triethylamine In cyclohexane at 0 - 20℃; for 3h; | A 11% B n/a |
A
- 518050-74-3
spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]
B
- 700-58-3
2-Adamantanone
| Conditions | Yield |
|---|---|
| With N-Bromosuccinimide In cyclohexane at 80℃; for 3h; | A 8% B n/a |
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Chemistry
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
Toxicity Data With Reference
| 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 Profile
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
Specification
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.