1,3-Dihydroxyadamantane supplier

Name
1,3-Dihydroxyadamantane
EINECS
CAS No. 5001-18-3
Article Data95
CAS DataBase
Density 1.368 g/cm³
Solubility Soluble in organic solvents,insoluble in water.
Melting Point ~260 °C
Formula C₁₀H₁₆O₂
Boiling Point 320.4 °C at 760 mmHg
Molecular Weight 168.236
Flash Point 158.5 °C
Transport Information
Appearance white crystal
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,3-Adamantanediol(6CI,7CI,8CI);1,3-Dihydroxy admantane;Tricyclo[3.3.1.13,7]decane-1,3-diol;
PSA 40.46000
LogP 1.06240

Synthetic route

: 16104-50-0
1,3-dichloroadamantane

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With water; sodium acetate In DMF (N,N-dimethyl-formamide) at 150℃; under 2175.22 Torr; for 18h; Product distribution / selectivity;	96%
With water; sodium acetate In ISOPROPYLAMIDE at 150℃; under 2175.22 Torr; for 18h; Product distribution / selectivity;	96%
With lithium acetate; water In DMF (N,N-dimethyl-formamide) at 150℃; under 2175.22 Torr; for 18h; Product distribution / selectivity;	96%

: 768-95-6
1-adamanthanol

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
Stage #1: 1-adamanthanol With sulfuric acid; acetic anhydride at 14 - 16℃; for 0.5h; Large scale; Stage #2: With nitric acid at 83 - 102℃; Temperature; Large scale; Further stages;	95.1%
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 60℃; for 8h;	92%
With Bromotrichloromethane; water; molybdenum hexacarbonyl at 150℃; for 6h; Inert atmosphere; regioselective reaction;	86%

: 84868-17-7
p-Toluolsulfonsaeure-(3-chlor-1-adamantyl)ester

A: 5001-18-3
1,3-adamantandiol

B: 772-26-9
1-chloro-3-hydroxyadamantane

Conditions

Conditions	Yield
With 1,4-dioxane; water; triethylamine solvolysis;	A 5% B 94%

: 876-53-9
1,3-dibromoadamantane

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
Stage #1: 1,3-dibromoadamantane With sodium formate In formic acid at 115 - 120℃; Large scale; Stage #2: With water at 80℃; Large scale;	91.7%
With water In acetone for 3h; Reflux;	68.5%
With silver nitrate In 1,4-dioxane
With acetone for 3h; Reflux;

: 281-23-2
adamantane

: 74087-85-7
3,3-dimethyldioxirane

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

E: 22635-62-7
1-acetyloxyadamantane

Conditions

Conditions	Yield
In acetone at 20℃; for 7.6h; Rate constant; Product distribution; Kinetics;	A 1.5% B 91.5% C 1% D 4.5% E 1.5%

...Expand

: 281-23-2
adamantane

A: 700-58-3
2-Adamantanone

B: 768-95-6
1-adamanthanol

C: 5001-18-3
1,3-adamantandiol

Conditions

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%

...Expand

: 281-23-2
adamantane

A: 768-95-6
1-adamanthanol

B: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With methyltrifluoromethyldioxirane In dichloromethane at -20℃; for 0.666667h;	A 4 % Chromat. B 86%
With acetic anhydride; periodic acid; chromoyl diacetate In dichloromethane; acetonitrile at -40 - 0℃; for 2h;	A 86% B n/a
With 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone; dihydrogen peroxide; acetic acid In 1,2-dichloro-ethane at 70℃; for 72h; Catalytic behavior; Reagent/catalyst; chemoselective reaction;	A 81% B 7%

: 281-23-2
adamantane

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; cobalt(II) acetate In dichloromethane at 0℃; for 3h; Reagent/catalyst;	83.4%
With chromium(VI) oxide; sulfuric acid; acetic acid at 80℃; for 2h;	71%
With N-hydroxyphthalimide; oxygen; cobalt acetylacetonate In acetic acid at 75℃; under 760 Torr; for 6h;	98 % Turnov.

: 84868-18-8
p-Toluolsulfonsaeure-(3-brom-1-adamantyl)ester

A: 5001-18-3
1,3-adamantandiol

B: 17933-29-8
7-methylenebicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
With 1,4-dioxane; water; triethylamine solvolysis;	A 75% B 2%

: 281-23-2
adamantane

: 111-27-3
hexan-1-ol

A: 5001-18-3
1,3-adamantandiol

B: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium hypochlorite	A n/a B 70%

...Expand

ruthenium chloride n-hydrate: ruthenium chloride n-hydrate

: 281-23-2
adamantane

: 111-27-3
hexan-1-ol

A: 5001-18-3
1,3-adamantandiol

B: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium hypochlorite In water; ethyl acetate	A 70% B n/a

...Expand

: 281-23-2
adamantane

A: 700-58-3
2-Adamantanone

B: 768-95-6
1-adamanthanol

C: 5001-18-3
1,3-adamantandiol

D: 772-26-9
1-chloro-3-hydroxyadamantane

Conditions

Conditions	Yield
With tetrachloromethane; water; molybdenum hexacarbonyl at 140℃; for 13h; Inert atmosphere;	A 10% B 70% C n/a D n/a

...Expand

: 39269-10-8
adamantane-1,3-dicarboxylic acid

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With manganese(IV) oxide; sulfuric acid at 43 - 47℃;	67%

: 281-23-2
adamantane

A: 5001-18-3
1,3-adamantandiol

B: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
	A n/a B 65%
With hydrogenchloride	A n/a B 61%
	A n/a B 52%
With methyltrifluoromethyldioxirane In dichloromethane at -20℃; for 2h;	A 8 % Chromat. B 90 % Chromat.
With C25H22FeN7O3(2+)*2ClO4(1-); dihydrogen peroxide In acetonitrile at 25℃; for 5h;	A 18.9 %Chromat. B 27.2 %Chromat.

: 24569-89-9
1,3-dehydroadamantane

A: 5001-18-3
1,3-adamantandiol

B: 772-26-9
1-chloro-3-hydroxyadamantane

Conditions

Conditions	Yield
With chromyl chloride In tetrachloromethane; dichloromethane at 0℃;	A 24% B 64%

: 41826-65-7
adamantane-1,3-dicarboxylic acid diethyl ester

: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With manganese(IV) oxide; sulfuric acid at 25 - 30℃;	63%

: 768-95-6
1-adamanthanol

A: 5001-18-3
1,3-adamantandiol

B: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
With manganese(IV) oxide; N-hydroxyphthalimide; oxygen; cobalt acetylacetonate In acetic acid at 60℃; under 760.051 Torr; for 30h; Reagent/catalyst; Concentration; Temperature; Time; chemoselective reaction;	A 39% B 52%

: 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

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%

...Expand

: 24569-89-9
1,3-dehydroadamantane

A: 5001-18-3
1,3-adamantandiol

B: 17933-29-8
7-methylenebicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane; acetone for 20h;	A 8% B 46%

: 281-23-2
adamantane

A: 768-95-6
1-adamanthanol

B: 5001-18-3
1,3-adamantandiol

C: 700-57-2
2-hydroxytricyclo<3.3.1.13,7>decane

D: 20098-16-2, 73346-81-3, 73346-82-4
tricyclo<3.3.1.13,7>decane-1-4ax-diol

Conditions

Conditions	Yield
With Absidia glauca (IMI239693) In N,N-dimethyl-formamide at 23℃; for 260h; Product distribution; var. fungi of the genus Absidia and times;	A 24% B 4% C 3% D 8%

...Expand

: 281-23-2
adamantane

: 64-19-7
acetic acid

A: 700-58-3
2-Adamantanone

B: 19066-22-9
2-acetoxyadamantane

C: 768-95-6
1-adamanthanol

D: 700-57-2
1-adamantanol

E: 5001-18-3
1,3-adamantandiol

F: 22635-62-7
1-acetyloxyadamantane

G: 56137-59-8
1-hydroxy-3-acetoxyadamantane

H: 29817-47-8
1,3-dihydroxyadamantane diacetate

Conditions

Conditions	Yield
With oxygen; vanadium trisacetylacetonate at 120℃; under 760.051 Torr; for 6h; Product distribution / selectivity;	A 3.8% B n/a C 22.3% D 3% E 3.8% F n/a G n/a H n/a
With oxygen; bis(acetylacetonate)oxovanadium at 120℃; under 760.051 Torr; for 6h; Product distribution / selectivity;	A 3.1% B n/a C 18% D 2.8% E 1.7% F n/a G n/a H n/a
With oxygen; ammonium metavanadate at 120℃; under 760.051 Torr; for 6h; Product distribution / selectivity;	A 1.5% B n/a C 10.1% D 1.5% E 0.6% F n/a G n/a H n/a

...Expand

: 768-95-6
1-adamanthanol

A: 5001-18-3
1,3-adamantandiol

B: Tricyclo[3.3.1.1]decane-1,4ax-diol

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 23℃; for 150h; culture of Absidia cylindrospora (I.M.I. 342950);	A 20% B 14%

: 880-52-4
N-(1-adamantyl)acetamide

A: 5001-18-3
1,3-adamantandiol

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

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

Conditions

Conditions	Yield
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

: 281-23-2
adamantane

A: 768-95-6
1-adamanthanol

B: 5001-18-3
1,3-adamantandiol

C: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
With hydrogenchloride; sodium hypochlorite; ruthenium trichloride In water; ethyl acetate at 46℃; for 0.6 - 6.66667h; pH=4 - 8.5;	A 5% B 4% C 0.3%
With chromium(VI) oxide; acetic acid In water at 100℃; Temperature; Time;

...Expand

: 281-23-2
adamantane

: 115464-59-0
methyltrifluoromethyldioxirane

A: 768-95-6
1-adamanthanol

B: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
In dichloromethane at -12.4℃; for 2h; Rate constant; Mechanism; Product distribution;	A 38 % Chromat. B 60 % Chromat.

...Expand

: 281-23-2
adamantane

: 74087-85-7
3,3-dimethyldioxirane

A: 768-95-6
1-adamanthanol

B: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
In dichloromethane; acetone at -12.4℃; for 2h; Rate constant;

...Expand

: 768-95-6
1-adamanthanol

A: 58652-35-0
1-hydroxy-3-fluoroadamante

B: 5001-18-3
1,3-adamantandiol

Conditions

Conditions	Yield
With difluoroether

: 1719-58-0
Chlorodimethylvinylsilane

: 5001-18-3
1,3-adamantandiol

: 1,3-bis(dimethylvinylsiloxy)adamantane

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling with ice;	97%

: 5001-18-3
1,3-adamantandiol

: 814-68-6
acryloyl chloride

: 216581-76-9
acrylic acid 3-hydroxy-1-adamantyl

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice;	90.9%

: 5001-18-3
1,3-adamantandiol

: 1,2-dihydro-benzocyclobutene-4-ylmethylvinylchlorosilane

: 1,3-bis[(1,2-dihydro-benzocyclobutene-4-yl)methylvinylsilyloxy]adamantane

Conditions

Conditions	Yield
With 1H-imidazole; dmap In tetrahydrofuran for 2h; Inert atmosphere;	90%

: 5001-18-3
1,3-adamantandiol

: 17933-29-8
7-methylenebicyclo[3.3.1]nonan-3-one

Conditions

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride In benzene at 70℃; for 12h;	88%
With p-toluenesulfonyl chloride In pyridine; benzene at 75℃; for 12h;	81%
With pyridine; p-toluenesulfonyl chloride In benzene
With pyridine; p-toluenesulfonyl chloride In benzene at 75℃; for 40h; Grob Fragmentation; Inert atmosphere;

: 307-24-4
undecafluorohexanoic acid

: 5001-18-3
1,3-adamantandiol

: 1005454-12-5
3-hydroxy-1-adamantyl perfluorohexanoate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 4h; Heating / reflux;	88%

: 64-18-6
formic acid

: 5001-18-3
1,3-adamantandiol

: 39269-10-8
adamantane-1,3-dicarboxylic acid

Conditions

Conditions	Yield
Stage #1: 1,3-adamantandiol With sulfuric acid In water at 20℃; for 1h; Stage #2: formic acid In water at 0 - 20℃; for 4h; Stage #3: With sodium hydroxide; sulfuric acid more than 3 stages;	85%
With sulfuric acid at 0 - 20℃; for 12h; Koch-Haaf Carboxylation;	79.5%
With sulfuric acid at 20℃; for 12h; Cooling with ice;	79.5%

: 5001-18-3
1,3-adamantandiol

: 108-46-3
recorcinol

: 945027-88-3
1,3-bis(2,4-dihydroxyphenyl)adamantane

Conditions

Conditions	Yield
toluene-4-sulfonic acid In 1,2-dimethoxyethane at 90℃; for 6h;	85%

: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

: 5001-18-3
1,3-adamantandiol

: 1166222-89-4
1,3-bis(4-hydroxy-3,5-dimethoxy-phenyl)-adamantane

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid In 1,2-dichloro-ethane	85%

: 5001-18-3
1,3-adamantandiol

: 93-91-4
1-phenylbutan-1,3-dione

: 2,2'-(1,3-adamantylene)bis(1-phenylbutane-1,3-dione)

Conditions

Conditions	Yield
With indium(III) triflate In 1,2-dichloro-ethane for 3h; Reflux;	83%

: 5001-18-3
1,3-adamantandiol

: 2524-64-3
chlorophosphoric acid diphenyl ester

: 1,3-bis(diphenylphosphate)adamantane

Conditions

Conditions	Yield
With pyridine at 60 - 95℃;	83%

: 5001-18-3
1,3-adamantandiol

: 75-36-5
acetyl chloride

: 29817-47-8
1,3-dihydroxyadamantane diacetate

Conditions

Conditions	Yield
1.) 0 deg C, 15 min, 2.) r.t., 1 h; reflux, 2 h;	82%

: 5001-18-3
1,3-adamantandiol

: 3687-28-3
aucuparin

: C38H40O6

Conditions

Conditions	Yield
With methanesulfonic acid In ethylene dibromide for 48h; Inert atmosphere;	82%

: 5001-18-3
1,3-adamantandiol

: 95-48-7
ortho-cresol

: 582311-10-2
1,3-bis(3-methyl-4-hydroxyphenyl)adamantane

Conditions

Conditions	Yield
toluene-4-sulfonic acid at 90℃; for 10h;	80%
With sodium hydroxide; phosphoric acid; p-toluenesulfonic acid monohydrate In nitrogen; water; toluene

acetylacetonatovanadium (III) (V(AA)3): acetylacetonatovanadium (III) (V(AA)3)

: 5001-18-3
1,3-adamantandiol

: 99181-50-7
adamantane-1,3,5-triol

Conditions

Conditions	Yield
With acetic acid	80%

: 5001-18-3
1,3-adamantandiol

: 3-methylenebicyclo<3.3.1>nonan-7-one

Conditions

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride In benzene at 75℃; for 12h;	80%
With dmap; p-toluenesulfonyl chloride In toluene at 130℃; for 1.5h; Microwave irradiation;	77%
With pyridine; p-toluenesulfonyl chloride at 70℃; for 6h;	70.4%

: 5001-18-3
1,3-adamantandiol

: 108-95-2
phenol

: 37677-93-3
4,4'-(1,3-Adamantanediyl)bisphenol

Conditions

Conditions	Yield
With trifluoroacetic acid for 20h; Reflux;	76%
With methanesulfonic acid In melt at 80 - 90℃; for 7h; Inert atmosphere;

: 108-05-4
vinyl acetate

: 5001-18-3
1,3-adamantandiol

: 1,3-bis(vinyloxy)adamantane

Conditions

Conditions	Yield
With sodium carbonate; bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 100℃; for 6h;	75%

: 75-89-8
2,2,2-trifluoroethanol

: 5001-18-3
1,3-adamantandiol

: 1058167-51-3
3-(2,2,2-trifluoroethoxy)adamantan-1-ol

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid at 40℃; for 3h;	75%
With trifluorormethanesulfonic acid at 40℃; for 2.5h;	75%

: 5001-18-3
1,3-adamantandiol

: 120-80-9
benzene-1,2-diol

: 128455-01-6
1,3-bis(3,4-dihydroxyphenyl)adamantane

Conditions

Conditions	Yield
With methanesulfonic acid at 80℃; for 3h; Inert atmosphere;	72%
With methanesulfonic acid at 80℃; for 3h;	20%

1,3-Dihydroxyadamantane Chemical Properties

Molecular Structure:
Molecular Formula: C₁₀H₁₆O₂
Molecular Weight: 168.23
CAS NO: 5001-18-3
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 18.46 Å²
Index of Refraction: 1.656
Molar Refractivity: 45.2 cm³
Molar Volume: 122.9 cm³
Surface Tension: 71.5 dyne/cm
Density: 1.368 g/cm³
Flash Point: 158.5 °C
Enthalpy of Vaporization: 65.15 kJ/mol
Boiling Point: 320.4 °C at 760 mmHg
Vapour Pressure: 2.59E-05 mmHg at 25°C
Melting Point: ~260 °C
Appearance: white crystal
SMILES: OC13CC2CC(O)(CC(C1)C2)C3
InChI: InChI=1/C10H16O2/c11-9-2-7-1-8(4-9)5-10(12,3-7)6-9/h7-8,11-12H,1-6H2
InChIKey: MOLCWHCSXCKHAP-UHFFFAOYAO
Std. InChI: InChI=1S/C10H16O2/c11-9-2-7-1-8(4-9)5-10(12,3-7)6-9/h7-8,11-12H,1-6H2
Std. InChIKey: MOLCWHCSXCKHAP-UHFFFAOYSA-N
Product Categories of 1,3-Dihydroxyadamantane (CAS NO.5001-18-3): Pharmaceutical Intermediates;Adamantane derivatives;Adamantanes

1,3-Dihydroxyadamantane Safety Profile

WGK Germany: 3

1,3-Dihydroxyadamantane Specification

The chemical synonyms of 1,3-Dihydroxyadamantane (CAS NO.5001-18-3): 1,3-AdamantandioL ; 1,3-DihydroxyadamantanE ; Adamantane-1,3-diol ; 1,3-Admantane-dimethanol ; 1,3-Admantane .

Product Name

1,3-Dihydroxyadamantane

Synthetic route

1,3-Dihydroxyadamantane Chemical Properties

1,3-Dihydroxyadamantane Safety Profile

1,3-Dihydroxyadamantane Specification

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