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2-Adamantanone

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Name

2-Adamantanone

EINECS 211-847-2
CAS No. 700-58-3 Density 1.105 g/cm3
PSA 17.07000 LogP 2.01160
Solubility methanol: 0.1 g/mL, clear Melting Point 256-258 °C (subl.)(lit.)
Formula C10H14O Boiling Point 246.7 °C at 760 mmHg
Molecular Weight 150.221 Flash Point 95.7 °C
Transport Information N/A Appearance white to off-white crystalline powder
Safety 22-24/25-36-26 Risk Codes 52-36/37/38
Molecular Structure Molecular Structure of 700-58-3 (2-Adamantanone) Hazard Symbols IrritantXi
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;

Article Data 338

2-Adamantanone Synthetic route

700-57-2

1-adamantanol

700-58-3

2-Adamantanone

Conditions
ConditionsYield
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%
281-23-2

adamantane

A

700-58-3

2-Adamantanone

B

768-95-6

1-adamanthanol

C

5001-18-3

1,3-adamantandiol

Conditions
ConditionsYield
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%
281-23-2

adamantane

A

700-58-3

2-Adamantanone

B

768-95-6

1-adamanthanol

Conditions
ConditionsYield
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%
4500-12-3

2-adamantanone oxime

700-58-3

2-Adamantanone

Conditions
ConditionsYield
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.

adamantane-2-spiro-3′-1′,2′,4′,5′,7′-pentaoxocane

95-54-5

1,2-diamino-benzene

A

700-58-3

2-Adamantanone

B

2Н,5Н-1,6-(methanedioxymethano)benzo[e][1,2,4,7]dioxadiazocine

Conditions
ConditionsYield
With samarium(III) nitrate hexahydrate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;A n/a
B 60%
281-23-2

adamantane

A

700-58-3

2-Adamantanone

B

768-95-6

1-adamanthanol

C

700-57-2

1-adamantanol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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)]

A

spiro[adamantan-2,2'-(5'-methylene-1',3'-dioxolan-4'-one)]

B

700-58-3

2-Adamantanone

Conditions
ConditionsYield
With triethylamine In cyclohexane at 0 - 20℃; for 3h;A 11%
B n/a

spiro[adamantan-2,2'-(5'-methyl-1',3'-dioxolan-4'-one)]

A

518050-74-3

spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]

B

700-58-3

2-Adamantanone

Conditions
ConditionsYield
With N-Bromosuccinimide In cyclohexane at 80℃; for 3h;A 8%
B n/a

2-Adamantanone Chemical Properties

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

2-Adamantanone 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.

2-Adamantanone Safety Profile

Safety Information about 2-Adamantanone (CAS NO.700-58-3):
Hazard Codes: IrritantXi
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

2-Adamantanone 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.

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