• Name

  2-Ethyl-2-adamantanol

• EINECS
• CAS No. 14648-57-8
• Article Data8
• CAS DataBase
• Density 1.045 g/cm³
• Solubility
• Melting Point 70 °C
• Formula C₁₂H₂₀O
• Boiling Point 265.5 °C at 760 mmHg
• Molecular Weight 180.29
• Flash Point 110.2 °C
• Transport Information
• Appearance
• Safety 24/25
• Risk Codes R36/37/38
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Adamantanol,2-ethyl- (8CI);2-Ethyl-2-hydroxytricyclo[3,3,1,1(3,7)])decane;Tricyclo[3.3.1.13,7]decan-2-ol,2-ethyl-;
• PSA 20.23000
• LogP 2.58360

Synthetic route

700-58-3

2-Adamantanone

811-49-4

ethyllithium

14648-57-8

2-ethyl-2-adamantanol

Conditions

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

700-58-3

2-Adamantanone

925-90-6

ethylmagnesium bromide

A

700-57-2

1-adamantanol

B

14648-57-8

2-ethyl-2-adamantanol

Conditions

Conditions	Yield
Stage #1: ethylmagnesium bromide With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran; diethyl ether at 20℃; Grignard addition; Stage #2: 2-Adamantanone In tetrahydrofuran; diethyl ether at 0℃; for 3h; Grignard addition;	A 16% B 80%
In tetrahydrofuran; diethyl ether at 0℃; Grignard addition;	A 80% B 18%

...Expand

10467-10-4

ethylmagnesium iodide

700-58-3

2-Adamantanone

75-03-6

ethyl iodide

A

700-57-2

1-adamantanol

B

14648-57-8

2-ethyl-2-adamantanol

Conditions

Conditions	Yield
With magnesium In tetrahydrofuran

...Expand

14648-57-8

2-ethyl-2-adamantanol

14451-87-7

2-ethyladamantane

Conditions

Conditions	Yield
With trifluoroacetic acid In hexane at 25 - 50℃; for 51h;	89%

14648-57-8

2-ethyl-2-adamantanol

C12H19N3

Conditions

Conditions	Yield
With sodium azide; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 28h;	80%
With sodium azide; trifluoroacetic acid In dichloromethane at 0 - 20℃; for 28h;	80%
With sodium azide; sulfuric acid; water In chloroform at 0 - 20℃;

14648-57-8

2-ethyl-2-adamantanol

74693-81-5

5-(1-iodoethylydene)-4-oxatricyclo<4.3.1.1.3,8>undecane

Conditions

Conditions	Yield
With lead(IV) acetate; iodine; calcium carbonate In benzene for 3h; Heating;	33%

14648-57-8

2-ethyl-2-adamantanol

A

700-58-3

2-Adamantanone

B

66633-37-2

2-Hydroxy-2-adamantyl methyl ketone

C

2-Acetoxy-2-adamantyl methyl ketone

D

2-(1-Acetoxyethyl)-2-adamantanol

Conditions

Conditions	Yield
With nitric acid; acetic anhydride at 20℃; for 1h; Further byproducts given;	A 32% B 10% C 15% D 19%

...Expand

14648-57-8

2-ethyl-2-adamantanol

A

700-58-3

2-Adamantanone

B

1-(2-Adamantylidene)-1-nitroethane

C

2-Acetoxy-2-adamantyl methyl ketone

D

2-(1-Acetoxyethyl)-2-adamantanol

Conditions

Conditions	Yield
With nitric acid; acetic anhydride at 20℃; for 1h; Further byproducts given;	A 32% B 7% C 15% D 19%

...Expand

14648-57-8

2-ethyl-2-adamantanol

108-24-7

acetic anhydride

A

700-58-3

2-Adamantanone

B

66633-37-2

2-Hydroxy-2-adamantyl methyl ketone

C

2-Acetoxy-2-adamantyl methyl ketone

D

2-(1-Acetoxyethyl)-2-adamantanol

Conditions

Conditions	Yield
With nitric acid at 20℃; for 1h; Further byproducts given;	A 32% B 10% C 15% D 19%

...Expand

14648-57-8

2-ethyl-2-adamantanol

79-04-9

chloroacetyl chloride

625122-38-5

2-chloroacetoxy-2-ethyladamantane

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 24.25h;	22.2%

14648-57-8

2-ethyl-2-adamantanol

13376-16-4

(1r,3r,5R*,7S*)-2-ethylideneadamantane

Conditions

Conditions	Yield
With iodine In xylene Heating;
With pyridine; thionyl chloride at -5℃;
With toluene-4-sulfonic acid In toluene

14648-57-8

2-ethyl-2-adamantanol

2-Bromo-2-ethyl-adamantane

Conditions

Conditions	Yield
With phosphorus tribromide

14648-57-8

2-ethyl-2-adamantanol

C12H19(1+)

Conditions

Conditions	Yield
With fluorosulfonylchloride; antimony pentafluoride; fluorosulphonic acid In dichloromethane-d2 at -140℃;

14648-57-8

2-ethyl-2-adamantanol

C13H18Cl2

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: I2 / xylene / Heating 2: aq. NaOH, 2NEt3>Cl / benzene View Scheme

14648-57-8

2-ethyl-2-adamantanol

129302-82-5

C12H19(2)H

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: PBr3 2: (n-Bu)3SnD / Irradiation View Scheme

14648-57-8

2-ethyl-2-adamantanol

374595-26-3

2-ethyl-2-adamantyl alkoxy lithium

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1.68333 - 1.7h;

700-58-3

2-Adamantanone

281-23-2

adamantane

14648-57-8

2-ethyl-2-adamantanol

A

209982-56-9

2-ethyladamantan-2-yl methacrylate

B

1187-03-7

N,N,N',N'-tetraethylurea

Conditions

Conditions	Yield
	A n/a B 6.3 wt %

...Expand

14648-57-8

2-ethyl-2-adamantanol

1215574-74-5

2-ethyltricyclo[3.3.1.1]decan-2-amine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; trifluoroacetic acid / dichloromethane / 28 h / 0 - 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 5 h / Reflux View Scheme

14648-57-8

2-ethyl-2-adamantanol

C21H28O5

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dmap / tetrahydrofuran / 0.5 h / 23 - 50 °C 1.2: 10 h / 50 °C 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 23 °C View Scheme

14648-57-8

2-ethyl-2-adamantanol

C22H14F7O2S(1+)*C23H27F2O9S(1-)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dmap / tetrahydrofuran / 0.5 h / 23 - 50 °C 1.2: 10 h / 50 °C 2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 6 h / 23 °C 3.1: 1 h / 23 °C View Scheme

826-62-0, 85081-15-8, 85081-16-9

5-norbornene-2,3-dicarboxylic anhydride

14648-57-8

2-ethyl-2-adamantanol

C21H28O4

Conditions

Conditions	Yield
Stage #1: 5-norbornene-2,3-dicarboxylic anhydride With dmap In tetrahydrofuran at 23 - 50℃; for 0.5h; Stage #2: 2-ethyl-2-adamantanol In tetrahydrofuran at 50℃; for 10h;

14648-57-8

2-ethyl-2-adamantanol

C5H3F2N2O4S(1-)*C22H14F7O2S(1+)

C22H14F7O2S(1+)*C14H19F2O5S(1-)

Conditions

Conditions	Yield
at 23℃; for 1h;

14648-57-8

2-ethyl-2-adamantanol

C18H15S(1+)*C20H25F2O9S(1-)

C18H15S(1+)*C32H43F2O9S(1-)

Conditions

Conditions	Yield
Stage #1: C18H15S(1+)*C20H25F2O9S(1-) With 1,1'-carbonyldiimidazole In chloroform at 23℃; for 0.5h; Stage #2: 2-ethyl-2-adamantanol In chloroform at 23℃; for 18h;

14648-57-8

2-ethyl-2-adamantanol

C18H15S(1+)*C21H23F2O9S(1-)

C18H15S(1+)*C33H41F2O9S(1-)

Conditions

Conditions	Yield
Stage #1: C18H15S(1+)*C21H23F2O9S(1-) With 1,1'-carbonyldiimidazole In chloroform at 23℃; for 0.5h; Stage #2: 2-ethyl-2-adamantanol In chloroform at 23℃; for 18h;

14648-57-8

2-ethyl-2-adamantanol

21286-54-4

Camphorsulfonyl chloride

C22H34O4S

Conditions

Conditions	Yield
Stage #1: 2-ethyl-2-adamantanol With pyridine In tetrahydrofuran at 23℃; for 0.5h; Stage #2: Camphorsulfonyl chloride In tetrahydrofuran at 5 - 23℃; for 19h;

14648-57-8

2-ethyl-2-adamantanol

313241-19-9

2-ethyltricyclo[3.3.1.13,7]decan-2-amine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide; trifluoroacetic acid / dichloromethane / 28 h / 0 - 20 °C 2: lithium aluminium tetrahydride / diethyl ether / 5 h / Reflux View Scheme

14648-57-8

2-ethyl-2-adamantanol

652-34-6

2,3,5,6-tetrafluoro-4-hydroxybenzoic acid

C19H20F4O3

Conditions

Conditions	Yield
Stage #1: 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 23 - 60℃; for 2h; Stage #2: 2-ethyl-2-adamantanol In acetonitrile at 60℃; for 2h;

14648-57-8

2-ethyl-2-adamantanol

618-83-7

5-Hydroxyisophthalic acid

C32H42O5

Conditions

Conditions	Yield
Stage #1: 5-Hydroxyisophthalic acid With 1,1'-carbonyldiimidazole In acetonitrile at 23 - 60℃; for 2h; Stage #2: 2-ethyl-2-adamantanol In acetonitrile at 60℃; for 2h;

2-Ethyl-2-adamantanol Chemical Properties

2-Ethyl-2-adamantanol Specification