Product Name

  • Name

    2-Adamantanone

  • EINECS 211-847-2
  • CAS No. 700-58-3
  • Article Data338
  • CAS DataBase
  • Density 1.105 g/cm3
  • 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
  • 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;
  • PSA 17.07000
  • LogP 2.01160

Synthetic route

1-adamantanol
700-57-2

1-adamantanol

2-Adamantanone
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%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
768-95-6

1-adamanthanol

C

1,3-adamantandiol
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%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
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%
2-adamantanone oxime
4500-12-3

2-adamantanone oxime

2-Adamantanone
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

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

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

A

2-Adamantanone
700-58-3

2-Adamantanone

B

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

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%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
768-95-6

1-adamanthanol

C

1-adamantanol
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%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
768-95-6

1-adamanthanol

C

1-adamantanol
700-57-2

1-adamantanol

D

1,3-adamantandiol
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%
adamantane-2-thione
23695-65-0

adamantane-2-thione

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

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

B

2-Adamantanone
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)]

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

A

spiro[adamantan-2,2'-(5'-bromo-5'-methyl-1',3'-dioxolan-4'-one)]
518050-74-3

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

B

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With N-Bromosuccinimide In cyclohexane at 80℃; for 3h;A 8%
B n/a
C20H23ClO3

C20H23ClO3

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h;84%
C18H18F6N2

C18H18F6N2

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-(3,5-bis(trifluoromethyl)phenyl)-3,5-dimethylpyrazole
1526941-41-2

1-(3,5-bis(trifluoromethyl)phenyl)-3,5-dimethylpyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 80%
B 91%
2,2-propanediyldimercaptoadamantane

2,2-propanediyldimercaptoadamantane

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
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%
C16H19BrN2

C16H19BrN2

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-(4-bromophenyl)-3,5-dimethylpyrazole hydrochloride
1526941-40-1

1-(4-bromophenyl)-3,5-dimethylpyrazole hydrochloride

Conditions
ConditionsYield
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%
C17H22N2

C17H22N2

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

3,5-dimethyl-1-(o-tolyl)-1H-pyrazole
91565-80-9

3,5-dimethyl-1-(o-tolyl)-1H-pyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 92%
B 91%
C16H20N2
1526941-45-6

C16H20N2

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

3,5-dimethyl-1-phenyl-1H-pyrazole
1131-16-4

3,5-dimethyl-1-phenyl-1H-pyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Reagent/catalyst; Inert atmosphere;A 92%
B 95%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

4-oxohomoadamantan-5-one
21898-84-0

4-oxohomoadamantan-5-one

C

1-adamanthanol
768-95-6

1-adamanthanol

D

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
With N-hydroxyphthalimide; ammonium cerium (IV) nitrate; oxygen In 1,2-dichloro-ethane at 40℃; for 24h;
adamantane
281-23-2

adamantane

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
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
72590-63-7

2-(methoxymethylene)adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

tricyclo<3.3.1.13,7>decane-2-spiro-3'-(4'-methoxy-1',2'-dioxetane)
73774-49-9

tricyclo<3.3.1.13,7>decane-2-spiro-3'-(4'-methoxy-1',2'-dioxetane)

C

C16H27NO3Si

C16H27NO3Si

Conditions
ConditionsYield
With trimethylsilyl cyanide; oxygen; 5,15,10,20-tetraphenylporphyrin In dichloromethane at -70℃; Irradiation;A 22%
B 30%
C 35%
adamantylidene-adamantane
30541-56-1

adamantylidene-adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

bisadamantylidene epoxide
29186-07-0

bisadamantylidene epoxide

Conditions
ConditionsYield
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)
19557-70-1

3.3.1.13,7.tricyclo 2-decane 2'-spiro(1',3'-dithiolanne)

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With (CH3)3CI; dimethyl sulfoxide for 12h;85%
With trimethylsilyl bromide; dimethyl sulfoxide In tetrachloromethane at 75 - 80℃; for 28h;75%
bis(adamantylidene)methane
28939-47-1

bis(adamantylidene)methane

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With oxygen; methylene blue In dichloromethane at 15℃; for 7.5h; Irradiation;87%
C20H24O3

C20H24O3

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 8h;62%
C17H22N2

C17H22N2

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-(4-methylphenyl)-3,5-dimethyl-1H-pyrazole
20157-46-4

1-(4-methylphenyl)-3,5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 80%
B 84%
C16H19FN2

C16H19FN2

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole
81329-48-8

1-(4-fluorophenyl)-3,5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 90%
B 84%
C21H31N3O2S

C21H31N3O2S

acetylacetone
123-54-6

acetylacetone

A

2-Adamantanone
700-58-3

2-Adamantanone

B

2-(3,5-dimethylpyrazol-1-yl)-N,N-diethyl-4-methylbenzenesulfonamide
1526941-42-3

2-(3,5-dimethylpyrazol-1-yl)-N,N-diethyl-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 87%
B 84%
C14H24N2

C14H24N2

acetylacetone
123-54-6

acetylacetone

A

1-butyl-3,5-dimethylpyrazole
2655-37-0

1-butyl-3,5-dimethylpyrazole

B

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 24h; Inert atmosphere;A 82%
B 86%
acetylacetone
123-54-6

acetylacetone

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

spiro[adamantane-2,3'-diazirine]
41736-95-2

spiro[adamantane-2,3'-diazirine]

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-benzyl-3,5-dimethyl-1H-pyrazole
1134-81-2

1-benzyl-3,5-dimethyl-1H-pyrazole

Conditions
ConditionsYield
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
281-23-2

adamantane

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
768-95-6

1-adamanthanol

C

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
In acetone at 22℃; for 18h; protected from light;A n/a
B 87%
C n/a
2-adamantylidene-N-tert-butylaziridine
113776-99-1

2-adamantylidene-N-tert-butylaziridine

A

2-Adamantanone
700-58-3

2-Adamantanone

B

N-methylene-tert-butylamine
13987-61-6

N-methylene-tert-butylamine

C

N-t-butylaziridinone
113777-00-7

N-t-butylaziridinone

Conditions
ConditionsYield
With oxygen; methylene blue In chloroform-d1 at 15℃; for 1h; Irradiation;A 100%
B 16 % Chromat.
C n/a
2-Adamantanone
700-58-3

2-Adamantanone

ethyllithium
811-49-4

ethyllithium

2-ethyl-2-adamantanol
14648-57-8

2-ethyl-2-adamantanol

Conditions
ConditionsYield
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
2-Adamantanone
700-58-3

2-Adamantanone

1-azidohexane
6926-45-0

1-azidohexane

4-hexyl-4-azahomoadamantane
138956-35-1

4-hexyl-4-azahomoadamantane

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane Ambient temperature;100%
With titanium tetrachloride In dichloromethane at 20℃; for 16h; Schmidt insertion;100%
2-Adamantanone
700-58-3

2-Adamantanone

sodium acetylide
1066-26-8

sodium acetylide

2-Ethynyl-2-hydroxyadamantane
70887-49-9

2-Ethynyl-2-hydroxyadamantane

Conditions
ConditionsYield
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
2-Adamantanone
700-58-3

2-Adamantanone

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

2-adamantanespiroxirane
24759-97-5

2-adamantanespiroxirane

Conditions
ConditionsYield
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;
2-Adamantanone
700-58-3

2-Adamantanone

propyllithium
2417-93-8

propyllithium

2-Propyl-2-adamantanol
14451-85-5

2-Propyl-2-adamantanol

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;100%
2-Adamantanone
700-58-3

2-Adamantanone

4-oxohomoadamantan-5-one
21898-84-0

4-oxohomoadamantan-5-one

Conditions
ConditionsYield
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%
2-Adamantanone
700-58-3

2-Adamantanone

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
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%
2-Adamantanone
700-58-3

2-Adamantanone

2-adamantanone oxime
4500-12-3

2-adamantanone oxime

Conditions
ConditionsYield
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%
2-Adamantanone
700-58-3

2-Adamantanone

acetonitrile
75-05-8

acetonitrile

2-adamantaneylideneacetonitrile
38121-89-0

2-adamantaneylideneacetonitrile

Conditions
ConditionsYield
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;
2-Adamantanone
700-58-3

2-Adamantanone

nitromethane
75-52-5

nitromethane

thiophenol
108-98-5

thiophenol

2-nitromethyl-2-phenylthioadamantane

2-nitromethyl-2-phenylthioadamantane

Conditions
ConditionsYield
With piperidine In benzene for 36h; Heating;100%
2-Adamantanone
700-58-3

2-Adamantanone

3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-adamantan-2-ol

2-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-adamantan-2-ol

Conditions
ConditionsYield
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
700-58-3

2-Adamantanone

1,1-dilithio-2,3,4,5-tetraphenyl-1-silacyclopentadiene
157895-14-2

1,1-dilithio-2,3,4,5-tetraphenyl-1-silacyclopentadiene

1-adamantan-2-ylidene-2,3,4,5-tetraphenyl-1H-silole

1-adamantan-2-ylidene-2,3,4,5-tetraphenyl-1H-silole

Conditions
ConditionsYield
In toluene at -78 - 20℃;100%
2-Adamantanone
700-58-3

2-Adamantanone

diethylphosphonoacetic acid methyl ester

diethylphosphonoacetic acid methyl ester

adamantylideneacetic acid methyl ester
98405-90-4

adamantylideneacetic acid methyl ester

Conditions
ConditionsYield
With sodium methylate In methanol; water100%
2-Adamantanone
700-58-3

2-Adamantanone

1,1'-biphenyl-2,2'-diamine
1454-80-4

1,1'-biphenyl-2,2'-diamine

N,N'-di(2-adamantyl) 1,1'-biphenyl-2,2'-diamine
868127-50-8

N,N'-di(2-adamantyl) 1,1'-biphenyl-2,2'-diamine

Conditions
ConditionsYield
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
700-58-3

2-Adamantanone

2-n-butyladamantanol-2
14451-86-6

2-n-butyladamantanol-2

Conditions
ConditionsYield
Stage #1: 2-Adamantanone With n-butyllithium In diethyl ether at -78℃; for 0.166667h;
Stage #2: With methanol
100%
2-Adamantanone
700-58-3

2-Adamantanone

hydrazinecarboxylic acid methyl ester
6294-89-9

hydrazinecarboxylic acid methyl ester

C12H18N2O2
544419-63-8

C12H18N2O2

Conditions
ConditionsYield
With acetic acid In methanol for 1h; Reflux;100%
2-Adamantanone
700-58-3

2-Adamantanone

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

N'-(adamantan-2-ylidene)-4-methylbenzenesulfonohydrazide
41780-69-2

N'-(adamantan-2-ylidene)-4-methylbenzenesulfonohydrazide

Conditions
ConditionsYield
In methanol at 20℃; Schlenk technique;100%
In methanol at 70℃; for 2h; Schlenk technique;
2-Adamantanone
700-58-3

2-Adamantanone

allyl bromide
106-95-6

allyl bromide

1-adamantyl-3-buten-1-ol

1-adamantyl-3-buten-1-ol

Conditions
ConditionsYield
With ammonium acetate; zinc In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;100%

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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