Product Name

  • Name

    3-Amino-1-hydroxyadamantane

  • EINECS 615-098-6
  • CAS No. 702-82-9
  • Article Data34
  • CAS DataBase
  • Density 1.252 g/cm3
  • Solubility Soluble in organic solvents,insoluble in water
  • Melting Point 265 °C (dec.)(lit.)
  • Formula C10H17NO
  • Boiling Point 266.8 °C at 760 mmHg
  • Molecular Weight 167.251
  • Flash Point 115.2 °C
  • Transport Information
  • Appearance slight yellow or white powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 702-82-9 (3-Amino-1-hydroxyadamantane)
  • Hazard Symbols IrritantXi
  • Synonyms 1-Adamantanol,3-amino- (7CI,8CI);(3-Hydroxyadamantan-1-yl)amine;1-Amino-3-adamantanol;1-Amino-3-hydroxyadamantane;3-Aminoadamantan-1-ol;
  • PSA 46.25000
  • LogP 1.72910

Synthetic route

3-nitroadamantan-1-ol
67496-92-8

3-nitroadamantan-1-ol

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
95%
amantadine hydrochloride
665-66-7

amantadine hydrochloride

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 10 - 15℃;90%
With sulfuric acid; nitric acid at 0 - 10℃; for 2h;81%
Stage #1: amantadine hydrochloride With sulfuric acid; nitric acid at 0 - 20℃; Inert atmosphere;
Stage #2: With sodium hydroxide In water		72%
1-Adamantanamine
768-94-5

1-Adamantanamine

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
Stage #1: 1-Adamantanamine With sulfuric acid; nitric acid In water at 5 - 25℃;
Stage #2: With water; sodium hydroxide at 0 - 40℃; for 1h;		90%
With sulfuric acid; nitric acid at 0 - 10℃; for 2h;81%
With Bromotrichloromethane; water; molybdenum hexacarbonyl at 150℃; for 6h; Inert atmosphere; regioselective reaction;80%
With sulfuric acid; nitric acid at 90℃; Temperature;
N-(3-hydroxyadamantan-1-yl)acetamide
778-10-9

N-(3-hydroxyadamantan-1-yl)acetamide

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With isopropyl alcohol; sodium hydroxide at 160℃; for 6h; Temperature; Reagent/catalyst; Autoclave; Inert atmosphere;90%
N-(1-adamantyl)acetamide
880-52-4

N-(1-adamantyl)acetamide

A

1,3-adamantandiol
5001-18-3

1,3-adamantandiol

B

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

C

N-(3-hydroxyadamantan-1-yl)acetamide
778-10-9

N-(3-hydroxyadamantan-1-yl)acetamide

Conditions
ConditionsYield
Stage #1: N-(1-adamantyl)acetamide With nitric acid
Stage #2: With acetic acid; urea In water		A 11%
B n/a
C 13%
...Expand
C10H17N*BF4(1-)*H(1+)

C10H17N*BF4(1-)*H(1+)

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With methyltrifluoromethyldioxirane; sodium carbonate 1.) CH3CN, CH2Cl2, 0 deg C, 3 h, 2.) CH2Cl2, RT, 5 h; Yield given. Multistep reaction;
3-methylenebicyclo<3.3.1>nonan-7-one

3-methylenebicyclo<3.3.1>nonan-7-one

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With ammonium hydroxide at 130℃;
amantadine hydrochloride
665-66-7

amantadine hydrochloride

A

3-hydroxytricyclo[3.3.1.13.7 ]decan-1-amine

3-hydroxytricyclo[3.3.1.13.7 ]decan-1-amine

B

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With sodium hydroxide
3-nitro-1-amantadine
243145-00-8

3-nitro-1-amantadine

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With sodium methylate In methanol at 30℃; for 0.5h; pH=> 14; Solvent; Reagent/catalyst;19.5g
With water; sodium hydroxide at 80℃; for 1.5h; pH=11 - 14; Temperature; pH-value;150.6 g
1-adamanthanol
768-95-6

1-adamanthanol

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 9,10-diphenylanthracene; tetrabutyl-ammonium chloride; methanol; cerium(III) chloride / acetonitrile / 1.1 h / 30 °C / Irradiation; Flow reactor; Inert atmosphere
2: dichloromethane / 2 h / 20 °C
3: hydrogen / methanol / 12 h / 20 °C
View Scheme
C10H18N2O*C2HF3O2

C10H18N2O*C2HF3O2

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; for 12h;
di-tert-butyl (3-hydroxyadamantan-1-yl)hydrazine-1,2-dicarboxylate

di-tert-butyl (3-hydroxyadamantan-1-yl)hydrazine-1,2-dicarboxylate

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 2 h / 20 °C
2: hydrogen / methanol / 12 h / 20 °C
View Scheme
3-bromoadamantane-1-carboxylic acid
21816-08-0

3-bromoadamantane-1-carboxylic acid

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Conditions
ConditionsYield
Stage #1: 3-bromoadamantane-1-carboxylic acid With diphenyl phosphoryl azide; triethylamine; tert-butyl alcohol at 80 - 110℃;
Stage #2: With hydrogen bromide Reflux;
Stage #3: With sodium hydroxide at 30℃;
4,6-dichloro-1H-indole-2-carboxylic acid
101861-63-6

4,6-dichloro-1H-indole-2-carboxylic acid

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

4,6-dichloro-N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

4,6-dichloro-N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;99%
2,4,6-trimethoxybenzaldehyde
830-79-5

2,4,6-trimethoxybenzaldehyde

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

3-((2,4,6-trimethoxybenzylidene)amino)adamantan-1-ol

3-((2,4,6-trimethoxybenzylidene)amino)adamantan-1-ol

Conditions
ConditionsYield
In benzene Reflux; Dean-Stark;99%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

tert-butyl (3-hydroxyadamantan-1-yl)carbamate
847795-89-5

tert-butyl (3-hydroxyadamantan-1-yl)carbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;97%
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 16h;65%
With triethylamine In tetrahydrofuran at 20℃; Cooling with ice;
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

chloroacetonitrile
107-14-2

chloroacetonitrile

(3-hydroxyadamantan-1-ylamino)acetonitrile

(3-hydroxyadamantan-1-ylamino)acetonitrile

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In ethyl acetate at 75℃;97%
Indole-2-carboxylic acid
1477-50-5

Indole-2-carboxylic acid

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;97%
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

Glyoxilic acid
298-12-4

Glyoxilic acid

[(3-hydroxyadamantan-1-yl)imino]acetic acid
1334337-69-7

[(3-hydroxyadamantan-1-yl)imino]acetic acid

Conditions
ConditionsYield
With acetic anhydride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Temperature; Reflux;96.1%
In tetrahydrofuran for 3h; Reflux;
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

glyoxalic acid monohydrate
6000-59-5

glyoxalic acid monohydrate

[(3-hydroxyadamantan-1-yl)imino]acetic acid
1334337-69-7

[(3-hydroxyadamantan-1-yl)imino]acetic acid

Conditions
ConditionsYield
With acetic anhydride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Temperature; Reflux;96.1%
5-methoxy-1H-indole-2-carboxylic acid
4382-54-1

5-methoxy-1H-indole-2-carboxylic acid

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

C20H24N2O3

C20H24N2O3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;96%
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

acetyl chloride
75-36-5

acetyl chloride

N-(3-hydroxyadamantan-1-yl)acetamide
778-10-9

N-(3-hydroxyadamantan-1-yl)acetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide95%
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

C9H11ClN2O3

C9H11ClN2O3

C19H27N3O4

C19H27N3O4

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In tetrahydrofuran at 20℃; for 12h; Temperature;93.4%
6-bromo-indole-2-carboxylic acid(Ref.7.)
16732-65-3

6-bromo-indole-2-carboxylic acid(Ref.7.)

3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

6-bromo-N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

6-bromo-N-(3-hydroxyadamantan-1-yl)-1H-indole-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;93%
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

benzaldehyde
100-52-7

benzaldehyde

3-benzylaminoadamantan-1-ol

3-benzylaminoadamantan-1-ol

Conditions
ConditionsYield
Stage #1: 3-aminoadamantan-1-ol; benzaldehyde In methanol for 3h; Reflux;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 5℃;		92.8%
Stage #1: 3-aminoadamantan-1-ol; benzaldehyde In methanol for 10h; Inert atmosphere; Reflux;
Stage #2: With methanol; sodium tetrahydroborate at 0 - 25℃;		80%
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

benzyl chloroformate
501-53-1

benzyl chloroformate

benzyl ((3-hydroxy)adamantan-1-yl)carbamate
565453-43-2

benzyl ((3-hydroxy)adamantan-1-yl)carbamate

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 20℃; for 2.16667h;92%
With potassium carbonate In tetrahydrofuran at 20℃; for 2h;85%
With potassium carbonate In tetrahydrofuran at 20℃; for 2h; Cooling with ice;
3-aminoadamantan-1-ol
702-82-9

3-aminoadamantan-1-ol

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
207557-35-5

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

(2S)-1-{[{2[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}[(3-hydroxytricyclo[3.3.1.1(3,7)]dec-1-yl)amino]]acetyl}pyrrolidine-2-carbonitrile
1036959-23-5

(2S)-1-{[{2[(2S)-2-cyanopyrrolidin-1-yl]-2-oxoethyl}[(3-hydroxytricyclo[3.3.1.1(3,7)]dec-1-yl)amino]]acetyl}pyrrolidine-2-carbonitrile

Conditions
ConditionsYield
With potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In dichloromethane at 30℃; for 3h; Solvent; Reagent/catalyst;91%
With potassium carbonate; potassium iodide In butanone for 4h; Reflux;77%
With potassium carbonate; potassium iodide In tetrahydrofuran for 5h; Product distribution / selectivity; Heating / reflux;72%

3-amino-1-adamantanol Specification

3-amino-1-adamantanol, with the CAS NO.702-82-9, has the Synonyms of TRICYCLO[3.3.1.13,7]DECAN-1-OL, 3-AMINO-; CHEMBRDG-BB 4003530; 3-AMINO-1-ADAMANTANOL; 3-Amino-1-hydroxyadamantane; 3-AMINOADAMANTAN-1-OL; AKOS BB-9784; 1-AMINO-3-ADAMANTANOL; 1-AMINO-3-HYDROXYADAMANTANE. It belongs to the Product Categories of Heterocycles series;Alcohols and Derivatives;Amines and Anilines;Adamantane derivatives;Amines;Adamantanes;Fused Ring Systems;Amino Alcohols;Organic Building Blocks;Oxygen Compounds.

Physical properties about 3-amino-1-adamantanol are: (1)ACD/LogP: 0.459; (2)ACD/LogD (pH 5.5): -2.64; (3)ACD/LogD (pH 7.4): -2.29; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.624; (12)Molar Refractivity: 47.167 cm3; (13)Molar Volume: 133.523 cm3; (14)Polarizability: 18.699 10-24cm3; (15)Surface Tension: 66.0400009155273 dyne/cm; (16)Density: 1.253 g/cm3; (17)Flash Point: 115.171 °C; (18)Enthalpy of Vaporization: 58.62 kJ/mol; (19)Boiling Point: 266.823 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

You can still convert the following datas into molecular structure:
(1)SMILES:C1C2CC3(CC1CC(C2)(C3)O)N;
(2)Std. InChI:InChI=1S/C10H17NO/c11-9-2-7-1-8(3-9)5-10(12,4-7)6-9/h7-8,12H,1-6,11H2/t7-,8+,9+,10-;
(3)Std. InChIKey:DWPIPTNBOVJYAD-FIRGSJFUSA-N;

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