1-Adamantanol supplier | CasNO.768-95-6

Name
1-Adamantanol
EINECS 212-202-8
CAS No. 768-95-6
Article Data460
CAS DataBase
Density 1.16 g/cm³
Solubility Soluble in ethanol , methanol, and diethyl ether. Partly miscible in water.
Melting Point 247 °C (subl.)(lit.)
Formula C₁₀H₁₆O
Boiling Point 245.8 °C at 760 mmHg
Molecular Weight 152.236
Flash Point 101.131 °C
Transport Information
Appearance white to off-white crystalline powder or needles
Safety 22-24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Tricyclo(3.3.1.1(sup 3,7))decan-1-ol (9CI);1-Adamantol;Tricyclo[3.3.1.13,7]decan-1-ol;Adapalene-1;1-Ad-OH;Tricyclo(3.3.1.13,7)decan-1-ol;1-Hydroxyadamantane;adamantan-1-ol;tricyclo[3.3.1.1~3,7~]decan-1-ol;
PSA 20.23000
LogP 1.94750

Synthetic route

: 768-93-4
1-iodoadamantane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 33℃; for 18h; Ultrasound with 20 KHz and bubbling of air;	100%
With 2,2'-azobis(isobutyronitrile); PVS; N-ethylpiperidinium hypophosphite In 1,4-dioxane; water at 100℃; for 0.5h;	72%
With PVS; (CH3)3N(+)(CH2)15CH3*H2PO2(-); 4,4'-dicyano-4,4'-azo-di-valeric acid In water at 100℃; for 1h;	70%

: 281-23-2
adamantane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 60h; Ambient temperature;	99%
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h; Reagent/catalyst; Temperature; Solvent;	99%
With water; bromine for 1h; Ambient temperature;	95%

: 828-51-3
1-Adamantanecarboxylic acid

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With sodium tetrahydroborate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; oxygen; caesium carbonate In dichloromethane at 40℃; for 40h; Irradiation;	99%
With manganese(IV) oxide; sulfuric acid at 25 - 30℃;	82%
Stage #1: 1-Adamantanecarboxylic acid With dipotassium hydrogenphosphate; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In chloroform at 20℃; for 48h; Schlenk technique; Irradiation; Green chemistry; Stage #2: With sodium tetrahydroborate In methanol; chloroform for 0.5h; Green chemistry;	40%

: 88773-89-1
2-(tricyclo[3.3.1.13,7]dec-1-yloxy)tetrahydro-2H-pyran

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 50h; Hydrolysis;	99%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In methanol; water for 1h; Ambient temperature;	96%
With methanol at 20℃; for 0.666667h;	92%

: 36960-53-9
1-trimethylsiloxyadamantane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.1h; Green chemistry;	99%
With poly (ethylene glycol)-sulfonated sodium montmorillonite nanocomposite In methanol at 20℃; for 0.333333h;	96%
With silicaphosphite (silphos), [PCl3-n(SiO2)n] In acetonitrile at 20℃; for 0.0333333h;	95%

: 768-90-1
1-Adamantyl bromide

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In acetic anhydride; acetic acid; N,N-dimethyl-formamide at 0 - 10℃; for 4h; Substitution; Electrochemical reaction;	98%
With water; bromine for 1h;	95.5%
With hydrogenchloride In N,N-dimethyl-formamide at 105℃; for 0.5h;	95%

: 281-23-2
adamantane

A: 700-58-3
2-Adamantanone

B: 768-95-6
1-adamanthanol

C: 700-57-2
1-adamantanol

Conditions

Conditions	Yield
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%

...Expand

: 1-adamantyl methoxyacetate

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With ytterbium(III) triflate In methanol at 50℃; for 36h;	97%

: 768-93-4
1-iodoadamantane

A: 281-23-2
adamantane

B: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen; tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 60℃; for 20h; Yields of byproduct given;	A n/a B 96%
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;	A 42% B n/a

: 76358-85-5
1-(tert-butyldimethylsiloxy)tricyclo[3.3.1.1]decane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With 2,5-bis(perfluorohexyl)-3,6-dichloro-1,4-benzoquinone In water; acetonitrile at 50℃; for 6h;	96%
With N-iodo-succinimide In methanol at 20℃; for 24h;	69%
sulfonic acid functionalized nanoporous silica In methanol at 35℃; for 24h;	50 % Chromat.

: pyridine-2-carboxylic acid adamantan-1-yl ester

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With zinc diacetate In methanol; dichloromethane at 38℃; for 30h;	96%

: 281-23-2
adamantane

: 76-05-1
trifluoroacetic acid

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
Stage #1: adamantane; trifluoroacetic acid With oxygen; sodium nitrite at 20℃; for 3h; Stage #2: With hydrogenchloride Further stages.;	96%

: 1036648-27-7
adamantan-1-yl 4-methylbenzoate

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In 1-methyl-pyrrolidin-2-one; isopropyl alcohol at 90℃; Electrochemical reaction; chemoselective reaction;	95%
With tetrabutylammonium tetrafluoroborate; isopropyl alcohol In 1-methyl-pyrrolidin-2-one at 90 - 100℃; Inert atmosphere; Electrolysis;	95%

: 220235-72-3
(3S,5S,7S)-1-((4-methoxybenzyl)oxy)adamantane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In water; acetonitrile at 20 - 30℃; for 5h; Irradiation; Green chemistry;	95%

: 135394-83-1
1-(2-propenyloxy)tricyclo<3.3.1.13,7>decane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With tert.-butyl lithium In pentane at -78 - 20℃; Substitution;	94%
With 1,3-dimethylbarbituric acid; Pd(PPh3) In tetrahydrofuran at 90℃; for 24h;	87%
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 90℃; for 24h;	86%

: 4-benzyloxy-butyric acid adamantan-1-yl ester

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
Stage #1: 4-benzyloxy-butyric acid adamantan-1-yl ester With hydrogen; palladium on activated charcoal In tetrahydrofuran under 760 Torr; for 24h; Stage #2: With potassium tert-butylate In tetrahydrofuran for 0.166667h;	93%

: 23569-25-7
1-adamantyl benzyl ether

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With water; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In acetonitrile at 20℃; for 8h;	93%
With triphenylphosphine hydrobromide In acetonitrile at 100℃; for 0.5h; Microwave irradiation; sealed tube;	83%

: 80514-85-8
Di(1-adamantyl)-tert-butylmethanol

A: 768-95-6
1-adamanthanol

B: 75-65-0
tert-butyl alcohol

Conditions

Conditions	Yield
With n-butyllithium In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 20℃; Product distribution;	A 8.6% B 92.4%

: 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

: 91233-19-1
1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With antimony triphenylsulphide In diethyl ether for 1h; Ambient temperature;	91%
With oxygen; thiophenol; antimony tris-benzenethiolate In diethyl ether for 0.5h; Ambient temperature;	91%

: 660427-99-6
(3r,5r,7r)-adamantan-1-ylboronic acid

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;	91%

: 1357000-33-9
2-((3r,5r,7r)-adamantan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation;	91%

: C13H17Cl3O3

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With trimethyltin(IV) hydroxide In 1,2-dichloro-ethane at 60℃; for 16h; Inert atmosphere; chemoselective reaction;	91%

: 75-05-8
acetonitrile

: 24325-56-2
trans-N,N'-bis(1-adamantyl)diazene

A: 3732-31-8
1,1'-Biadamantane

B: 281-23-2
adamantane

C: 768-95-6
1-adamanthanol

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

Conditions

Conditions	Yield
With thianthrene cation radical perchlorate Ambient temperature; Further byproducts given;	A 3% B 0.3% C 0.6% D 90%

...Expand

: 75-05-8
acetonitrile

: 24325-56-2
trans-N,N'-bis(1-adamantyl)diazene

A: 3732-31-8
1,1'-Biadamantane

B: 768-95-6
1-adamanthanol

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

D: 1660-04-4
1-acetyladamantane

Conditions

Conditions	Yield
With thianthrenium perchlorate Ambient temperature; Further byproducts given;	A 2.5% B 0.6% C 90% D 5.5%

...Expand

: 281-23-2
adamantane

A: 768-95-6
1-adamanthanol

B: 7575-82-8
1-nitroadamantane

C: 32314-61-7
1-nitroxyadamantane

Conditions

Conditions	Yield
With Nitrogen dioxide; ozone In dichloromethane at -78℃; for 0.5h;	A n/a B 90% C n/a
With methanesulfonic acid; dinitrogen pentoxide In dichloromethane at 0℃; for 1h;

...Expand

: 89849-39-8
Di(1-adamantyl)(1-norbornyl)methanol

A: 768-95-6
1-adamanthanol

B: 51566-98-4
1-norbornyl alcohol

Conditions

Conditions	Yield
With n-butyllithium In N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at 20℃; Product distribution;	A 89.7% B 10.3%

: 58652-54-3
1-adamantyl trifluoroacetate

: 768-95-6
1-adamanthanol

Conditions

Conditions	Yield
With sodium hydroxide In water at 100℃; for 0.5h;	89%
With potassium hydroxide In ethanol; water at 25℃; for 0.5h; Yield given;
With sodium carbonate for 2h; Heating; Yield given;

: 281-23-2
adamantane

: 76-05-1
trifluoroacetic acid

A: 768-95-6
1-adamanthanol

B: 34909-02-9
2-adamantyl trifluoroacetate

Conditions

Conditions	Yield
With peracetic acid; ruthenium trichloride In dichloromethane; ethyl acetate at 20℃; for 2h;	A 89% B 9%

...Expand

: 341-02-6
trityl tetrafluoroborate

: 133859-39-9
1-<(methylthio)methoxy>tricyclo<3.3.1.13,7>decane

A: 76-84-6
triphenylmethyl alcohol

B: 768-95-6
1-adamanthanol

C: 62575-83-1
triphenmethyl methyl sulfide

Conditions

Conditions	Yield
In dichloromethane for 0.25h; Ambient temperature;	A 77% B 88% C 16%
In dichloromethane for 0.25h; Product distribution; Mechanism; Ambient temperature; quenching with aq. NaHCO3, other trityl salts;	A 77% B 88% C 16%

...Expand

: 768-95-6
1-adamanthanol

: 935-56-8
1-chloroadamantane

Conditions

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 18h;	100%
With chlorosulfonic acid In chloroform at 10 - 15℃; for 8h;	96%
With indium(III) chloride; dimethylmonochlorosilane; benzil In dichloromethane at 20℃; for 82h;	93%

: 75-15-0
carbon disulfide

: 768-95-6
1-adamanthanol

: 74-88-4
methyl iodide

: 79057-62-8
O-(adamantan-1-yl) S-methyl carbonodithioate

Conditions

Conditions	Yield
Stage #1: carbon disulfide; 1-adamanthanol With 1H-imidazole; sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 0.5h;	100%
Stage #1: carbon disulfide; 1-adamanthanol With sodium hydride In tetrahydrofuran at 20℃; for 10h; Addition; Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 1h; Methylation;	78%
Stage #1: 1-adamanthanol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 2h; Stage #2: carbon disulfide In tetrahydrofuran; mineral oil at 0 - 20℃; for 15h; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0℃; for 2h;	72%

...Expand

: 106-41-2
4-bromo-phenol

: 768-95-6
1-adamanthanol

: 104224-68-2
2-(1-adamantyl)-4-bromophenol

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 20℃; for 48h; Friedel Crafts alkylation;	100%
With sulfuric acid; acetic acid In dichloromethane at 20℃; for 24h;	100%
With sulfuric acid; acetic acid In dichloromethane at 20℃; for 48h; Friedel-Crafts Alkylation; Large scale;	99%

: 768-95-6
1-adamanthanol

: 108-24-7
acetic anhydride

: 22635-62-7
1-acetyloxyadamantane

Conditions

Conditions	Yield
With magnesium(II) perchlorate at 20℃; for 0.33h;	100%
With tin(IV) tetraphenylporphyrin perchlorate at 20℃; for 0.25h;	99%
With silica gel for 0.0583333h; Microwave irradiation; neat (no solvent);	99%

: 768-95-6
1-adamanthanol

: 29558-77-8
4-bromo-4'-hydroxybiphenyl

: 496868-80-5
4-(4'-bromophenyl)-2-(adamantan-1-yl)phenol

Conditions

Conditions	Yield
With sulfuric acid; acetic acid at 25℃; for 72h; Friedel-Crafts reaction;	100%
With sulfuric acid; acetic acid at 20℃; for 96h;	100%
With sulfuric acid; acetic acid at 20℃; for 96h;	100%
With sulfuric acid In acetone at 20℃; for 96h; Cooling with ice;	100%
Friedel-Crafts alkylation;

: 768-95-6
1-adamanthanol

: 3179-31-5
2,4-dihydro-[1,2,4]triazole-3-thione

: 1-(1-adamantyl)-3-[(1-adamantyl)sulfanyl]-1,2,4-triazole

Conditions

Conditions	Yield
With sulfuric acid at 20℃; for 4h;	100%
With phosphoric acid; acetic acid at 40 - 42℃; for 5h;	100%

: tetraphenylbismuth(V) fluoride

: 768-95-6
1-adamanthanol

: 38614-05-0
(3s,5s,7s)-1-phenoxyadamantane

Conditions

Conditions	Yield
With N-Methyldicyclohexylamine; copper diacetate In toluene at 20℃; for 1h;	100%

: 768-95-6
1-adamanthanol

: 108-95-2
phenol

: 29799-07-3
4-adamantylphenol

Conditions

Conditions	Yield
With trifluoroacetic acid at 20℃; for 6h; Inert atmosphere;	100%
With trifluoroacetic acid at 20℃; for 12h;	85%
With trifluoroacetic acid	79%
With sulfuric acid In dichloromethane at 20℃; Inert atmosphere;	23%
With sulfuric acid In dichloromethane at 20℃; Inert atmosphere;

: 768-95-6
1-adamanthanol

: 18544-54-2, 122676-68-0, 14760-23-7
cobalt(II) bis(trimethylsilyl)amide

: bis(1-adamantoxo)cobalt(II)

Conditions

Conditions	Yield
In benzene under Ar, refluxed briefly; filtered, washed with ether, elem. anal.;	100%

: 768-95-6
1-adamanthanol

: 108-88-3
toluene

: 1459-55-8
4-(1-adamantyl)toluene

Conditions

Conditions	Yield
With indium(III) triflate; acetylacetone for 2h; Reflux; Green chemistry;	100%
With trifluoroacetic acid at 20℃; for 12h;	86%

: 768-95-6
1-adamanthanol

: 616-38-6
carbonic acid dimethyl ester

: 6221-74-5
1-methoxyadamantane

Conditions

Conditions	Yield
With tungsten hexacarbonyl at 180℃; for 1h; chemoselective reaction;	100%

: 768-95-6
1-adamanthanol

: 1391992-92-9
2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate

: C37H38O8

Conditions

Conditions	Yield
Stage #1: 1-adamanthanol; 2,3,4-tri-O-benzyl-L-rhamnopyranosyl ortho-hex-1-ynylbenzoate In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Molecular sieve; Stage #2: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Molecular sieve;	100%

: 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl trichloroacetimidate

: 768-95-6
1-adamanthanol

: 1-(adamantan-1-yl)-2,3-di-O-benzyl-4,6-benzylidene-β-D-mannopyranose

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; Molecular sieve; Inert atmosphere; stereoselective reaction;	100%

: 768-95-6
1-adamanthanol

A: 281-23-2
adamantane

B: 773-32-0
2-(1-adamantyl)propane

Conditions

Conditions	Yield
With triisopropylborane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -30 deg C, 30 min 2.) room temp., 6 h;	A 99.9% B 0.1%

: 768-95-6
1-adamanthanol

: 107-14-2
chloroacetonitrile

: 5689-59-8
N-(1-adamantyl)-2-chloroacetamide

Conditions

Conditions	Yield
Stage #1: 1-adamanthanol; chloroacetonitrile With sulfuric acid In acetic acid; N,N-dimethyl-formamide at 20 - 80℃; Stage #2: With water In acetic acid; N,N-dimethyl-formamide at 70℃;	99.6%
Stage #1: 1-adamanthanol; chloroacetonitrile With acetic acid In N,N-dimethyl-formamide Stage #2: With sulfuric acid; water In N,N-dimethyl-formamide at 20 - 80℃; Product distribution / selectivity;	99.6%
With sulfuric acid; acetic acid at 20℃; for 5h; Ritter reaction;	95%
With indium(III) triflate In sulfur dioxide at -50 - 100℃; for 24h; Ritter Amidation; Inert atmosphere; Autoclave; liquid SO2;	79%

: 768-95-6
1-adamanthanol

: 75-05-8
acetonitrile

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

Conditions

Conditions	Yield
With copper(ll) bromide at 150℃; for 8h; Reagent/catalyst; Ritter Amidation; Inert atmosphere; Sealed tube;	99%
With trifluoromethylsulfonic anhydride; sodium hydrogencarbonate In dichloromethane for 2h; Ambient temperature;	98%
With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 140℃; for 0.416667h; Ritter Amidation; Microwave irradiation; Green chemistry;	95%

: 768-95-6
1-adamanthanol

: 768-90-1
1-Adamantyl bromide

Conditions

Conditions	Yield
With oxygen; 1,2-dibromomethane for 10h; Reflux;	99%
With iron(III)-acetylacetonate; carbon tetrabromide at 120℃; for 2h; Sealed tube; Inert atmosphere;	99%
With dibromo sulfoxide In toluene for 22h;	96%

: 768-95-6
1-adamanthanol

: 281-23-2
adamantane

Conditions

Conditions	Yield
With hydrogen; aluminum oxide; nickel at 180℃;	99%
With indium(III) chloride; diphenylsilyl chloride In 1,2-dichloro-ethane at 80℃; for 3h;	99%
With boron trifluoride diethyl etherate In water for 2h; Inert atmosphere; Reflux;	29%

: 768-95-6
1-adamanthanol

: 70-55-3
toluene-4-sulfonamide

: 56432-99-6
1-tosylaminoadamantane

Conditions

Conditions	Yield
With iron(III) chloride In 1,2-dichloro-ethane at 50℃; for 24h; Inert atmosphere; Sealed tube;	99%
With oxalic acid; 2,3,4,5-tetrafluorophenyl(dihydroxy)borane In nitromethane at 20℃;	87%
With sulfuric acid for 2h;	66%

: 768-95-6
1-adamanthanol

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 36960-53-9
1-trimethylsiloxyadamantane

Conditions

Conditions	Yield
iodine In dichloromethane at 20℃; for 0.1h; Substitution;	99%
With silica-supported ZnCl2 (30%) In acetonitrile at 20℃; for 0.35h;	98%
With aluminum tris(dihydrogen phosphate) at 20℃; for 0.933333h;	97%

: 768-95-6
1-adamanthanol

: 74-88-4
methyl iodide

: 6221-74-5
1-methoxyadamantane

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran	99%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 20h;	81%
With sodium hydride In tetrahydrofuran
Stage #1: 1-adamanthanol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

: 7677-24-9
trimethylsilyl cyanide

: 768-95-6
1-adamanthanol

: 36960-53-9
1-trimethylsiloxyadamantane

Conditions

Conditions	Yield
With zinc(II) fluoride In dichloromethane for 18h;	99%

: 768-95-6
1-adamanthanol

: 100-47-0
benzonitrile

: 19026-84-7
N-(adamantan-1-yl)benzamide

Conditions

Conditions	Yield
With copper(ll) bromide at 150℃; for 6h; Ritter Amidation; Inert atmosphere; Sealed tube;	99%
With bismuth(lll) trifluoromethanesulfonate; water Ritter reaction;	91%
With water; tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 140℃; for 0.416667h; Ritter Amidation; Microwave irradiation; Green chemistry;	90%

: 768-95-6
1-adamanthanol

: 339276-10-7
2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate

: Acetic acid (2R,3R,4R,5S,6S)-4,5-diacetoxy-2-(adamantan-1-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 25℃; for 3h;	99%

: 768-95-6
1-adamanthanol

: 339276-12-9
2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

: 1-adamantanyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 25℃; for 3h;	99%

: 768-95-6
1-adamanthanol

: 125065-63-6, 134309-08-3
25,27-bis(benzyloxy)-26,28-dihydroxycalix[4]arene

: 5,11,17,23-tetrakis(1-adamantyl)-calix[4]arene

Conditions

Conditions	Yield
With trifluoroacetic acid In chloroform at 60 - 65℃; for 9h;	99%

1-Adamantanol Specification

1. Introduction of 1-Adamantanol
1-Adamantanol is also called Tricyclo[3.3.1.1(3,7)]decan-1-ol ; Tricyclo[3.3.1.1]decan-1-ol ; 1-Adamantol ; 1-Adamatanol ; Damantol-(1) ; Tricyclo(3.3.1.1(sup3,7))decan-1-ol ; 1-Hydroxydiamantane.

2. Properties of 1-Adamantanol
Melting Point: 247 °C (subl.)(lit.)
Flash Point: 240°C
Boiling Point: 245.8 °C at 760 mmHg
Freely Rotating Bonds: 1
Polar Surface Area: 9.23 Å2
Index of Refraction: 1.58
Molar Refractivity: 43.71 cm3
Molar Volume: 131.1 cm3
Surface Tension: 49.3 dyne/cm
Enthalpy of Vaporization: 56.11 kJ/mol
Vapour Pressure: 0.00466 mmHg at 25°C
Appearance: white to off-white crystalline powder or needles

3. Structure Descriptors of 1-Adamantanol
InChI=1S/C10H16O/c11-10-4-7-1-8(5-10)3-9(2-7)6-10/h7-9,11H,1-6H2

4. Toxicity of 1-Adamantanol

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	600mg/kg (600mg/kg)		Pharmaceutical Chemistry Journal Vol. 10, Pg. 454, 1976.

5. Safety Information of 1-Adamantanol
Hazard Codes: Irritant

Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36-26
S22: Do not breathe dust.
S24/25: Avoid contact with skin and eyes.
S36: Wear suitable protective clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: AU4980000
Hazard Note: Irritant
HS Code: 29061900

6. Use of 1-Adamantanol
1-Adamantanol is used to make adamantane derivatives and adapalene.

7. Storage and transportation of 1-Adamantanol
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Avoid to contact water or moisture during storing and transporting.

Product Name

1-Adamantanol

Synthetic route

1-Adamantanol Specification

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