Conditions | Yield |
---|---|
With triethylsilane; dilauryl peroxide; 1-dodecylthiol at 70℃; for 1h; | 100% |
With triethylsilane; dilauryl peroxide; 1-dodecylthiol In cyclohexane at 80℃; for 1h; | 100% |
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); cPS-SnBu2Cl In 1,2-dimethoxyethane at 80℃; for 0.5h; | 100% |
1-adamantyl isocyanide
adamantane
Conditions | Yield |
---|---|
With Perbenzoic acid; diphenylsilane In 1,4-dioxane for 1h; Heating; | 100% |
1-(phenylseleno)tricyclo<3.3.1.13,7>decane
adamantane
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In ethyl acetate for 14h; Reduction; Heating; | 100% |
With Perbenzoic acid; methyl phosphite In 1,4-dioxane for 5h; Heating; | 41 % Chromat. |
O-(adamantan-1-yl) S-methyl carbonodithioate
adamantane
Conditions | Yield |
---|---|
With sodium formate; (Bu4N)2S2O8 In N,N-dimethyl-formamide at 75℃; for 0.5h; Barton-McCombie deoxygenation; | 100% |
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 130℃; for 0.0833333h; Barton-McCombie deoxygenation; | 77% |
With 1-ethyl-piperidine; 2,2'-azobis(isobutyronitrile); hypophosphorous acid In 1,4-dioxane for 1h; | 100 % Chromat. |
With dibutylphosphine oxide; 1,1'-azobis(1-cyanocyclohexanenitrile) In 1,4-dioxane for 8h; Heating; | 90 % Chromat. |
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% |
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% |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; nickel at 170℃; | 99% |
Multi-step reaction with 2 steps 1: 81 percent / NaI; HI / 48 h / 90 - 100 °C 2: 35 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation View Scheme | |
Multi-step reaction with 2 steps 1: 81 percent / NaI; HI / 48 h / 90 - 100 °C 2: 20 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation View Scheme |
Conditions | Yield |
---|---|
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h; | 98% |
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h; Product distribution; sonication, other C(4n+6)H(4n+12), (n=1-3), other polycyclic hydrocarbon, other reactants, reaction condition; | 98% |
With aluminium trichloride at 150 - 180℃; | |
Mechanism; application of the "prinzip of minimal chemical distance"; |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); (C6F13CH2CH2)3SnH; sodium cyanoborohydride In tert-butyl alcohol at 90℃; for 3h; | 98% |
With air; tributyl borane; water In benzene at 20℃; | 97% |
With 1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane In 1,2,3-trifluorobenzene at 140℃; for 12h; | 97% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; oxygen-18 In tert-butyl alcohol at 60℃; for 16h; Yields of byproduct given; | A n/a B 98% |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; nickel at 235℃; under 760 Torr; for 4h; | 97% |
Octahydro-1,2,4-metheno-1H-cyclobutapentalene
adamantane
Conditions | Yield |
---|---|
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h; | 97% |
1-acetyloxyadamantane
adamantane
Conditions | Yield |
---|---|
With hafnium(IV) trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen In neat (no solvent) at 125℃; under 750.075 Torr; for 18h; Time; | 97% |
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h; | 85% |
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; water for 44h; Heating; | 97% |
Conditions | Yield |
---|---|
With triethylsilane; 2C2H3F3O*BF3 In dichloromethane at 20℃; for 3h; | 97% |
With gallium(III) triflate; dimethylmonochlorosilane In dichloromethane at 20℃; for 0.5h; | 88% |
With triethylsilane; 2C24BF20(1-)*C21H16N3P(2+) In dichloromethane at 120℃; for 13h; Inert atmosphere; | 94 %Spectr. |
1-Adamantyl bromide
trimethylstannane
A
adamantane
B
n-butyltrimethyltin
Conditions | Yield |
---|---|
With n-butyllithium In hexane 1-bromoadamantane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC; | A 97% B 95% |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; nickel at 200℃; | 96% |
With cerium(III) chloride; 9,10-diphenylanthracene; 1,2-bis(2,4,6-triisopropylphenyl)disulfane; tetrabutyl-ammonium chloride In acetonitrile for 24h; Irradiation; Inert atmosphere; | 95% |
bi(cyclopentadiene)
adamantane
Conditions | Yield |
---|---|
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h; | 96% |
With sodium tetrahydroborate; trifluoric acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h; Product distribution; other unsaturated polycyclics; | 96% |
1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione
adamantane
Conditions | Yield |
---|---|
With 9-borabicyclo[3.3.1]nonane dimer; tri-n-butyl-tin hydride In toluene at 0℃; | 96% |
With thiophenol In tetrahydrofuran at -80℃; Product distribution; Mechanism; Irradiation; | |
With 2,2'-azobis(isobutyronitrile); Tris(trimethylsilyl)methane In benzene at 80℃; | 89 % Chromat. |
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 |
Conditions | Yield |
---|---|
With [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride; isopropyl alcohol; sodium t-butanolate at 100℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; | 95% |
With air; diethylzinc; tri-n-butyl-tin hydride In benzene at 20℃; for 1h; | 90% |
With water; zinc In acetonitrile at 80℃; for 41h; Inert atmosphere; Sealed tube; | 53% |
octahydro-4,7-methano-inden-5-one
adamantane
Conditions | Yield |
---|---|
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h; | 95% |
Conditions | Yield |
---|---|
With hydrogen; aluminum oxide; nickel at 180℃; Pd/SiO2, 330 deg C; | 95% |
Multi-step reaction with 2 steps 1: DCC, DMAP 2: 93 percent / Bu3SnH, AIBN / benzene / 3 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 28 percent / 85percent H2O2 2: 3 percent Chromat. / cyclohexane / 81 °C View Scheme |
1,3-dichloroadamantane
adamantane
Conditions | Yield |
---|---|
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium; N,N-diethyl-1,1,1-trimethylsilanamine In diethyl ether for 6h; Ambient temperature; | 95% |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; Irradiation; | A 3% B n/a C 95% |
C24H25NO2Se
adamantane
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 3h; Heating; | 93% |
adamantane-1-carboxylate
adamantane
Conditions | Yield |
---|---|
With triethylsilane; C19H3BF14 In dichloromethane at 20℃; Inert atmosphere; Schlenk technique; | 93% |
ethyl dispiro[1,3-dithiolane-2',2;4',2''-bis(adamantane)]-5'-carboxylate
A
adamantane
B
(2-Adamantyl)essigsaeure-ethylester
Conditions | Yield |
---|---|
nickel In methanol | A n/a B 92% |
Conditions | Yield |
---|---|
With zirconocene dichloride; triethyl borane In tetrahydrofuran; hexane at 25℃; for 5h; | 92% |
With iron(III) chloride; phenylsilane; sodium methylate In tetrahydrofuran for 12h; Schlenk technique; Inert atmosphere; | 89% |
With Schwartz's reagent; triethyl borane In tetrahydrofuran at 25℃; for 17h; | 88% |
Conditions | Yield |
---|---|
With azobisisobutyronitrile; sodium cyanoborohydride In α,α,α-trifluorotoluene; tert-butyl alcohol | 92% |
With azobisisobutyronitrile; sodium cyanoborohydride In α,α,α-trifluorotoluene; tert-butyl alcohol | 92% |
Conditions | Yield |
---|---|
In water-d2; d(4)-methanol at 19.84℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; carbon tetrabromide Reagent/catalyst; Sealed tube; Inert atmosphere; | A 99% B 23% |
With bromine; iron at 0 - 50℃; for 3h; | A n/a B 93% |
With iodine(I) bromide In tetrachloromethane for 3h; Heating; | A 75 % Chromat. B 25 % Chromat. |
With iodine(I) bromide In tetrachloromethane for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
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% |
adamantane
1-(1-adamantyl)chlorophosphinoyladamantane
Conditions | Yield |
---|---|
With aluminum (III) chloride; phosphorus trichloride for 6.16667h; Reflux; | 99% |
Stage #1: adamantane With aluminum (III) chloride; phosphorus trichloride Reflux; Stage #2: With water Cooling with ice; | 99% |
With aluminium trichloride; phosphorus trichloride for 5h; Heating; | 95% |
With aluminium trichloride; phosphorus trichloride for 5h; Heating; | 86.2% |
With aluminium trichloride; water; phosphorus trichloride 1.) reflux, 6 h, 2.) chloroform; Yield given. Multistep reaction; |
adamantane
adamantane-d16
Conditions | Yield |
---|---|
With d8-isopropanol; 5% rhodium-on-charcoal; 10% Pt/activated carbon; water-d2 at 120℃; for 24h; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With bromine; Nitrogen dioxide In trifluoroacetic acid at 20℃; for 0.5h; | 98% |
With water; bromine for 0.166667h; | 93% |
With bromine at 85 - 110℃; Temperature; | 93% |
adamantane
1,3-dichloroadamantane
Conditions | Yield |
---|---|
With Iodine monochloride In tetrachloromethane for 5h; Heating; | 98% |
With chlorosulfonic acid at 0 - 25℃; for 10h; | 98% |
With chlorosulfonic acid at 0 - 25℃; for 8h; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With tetrachloromethane; manganese(III) acetylacetonate; acetonitrile at 200℃; for 1h; | 98% |
With Iodine monochloride In tetrachloromethane for 0.25h; Ambient temperature; | 97% |
With tetrachloromethane; ferrocene; ethanol at 160℃; for 6h; Sealed tube; | 93% |
Conditions | Yield |
---|---|
With tetrachloromethane; K10 bentonite; iron(III) chloride for 40h; Heating; | A 2% B 98% |
With tetrachloromethane; bis(acetylacetonate)oxovanadium; water at 160℃; for 6h; Sealed tube; | A 90% B n/a |
With thionyl chloride; n-Butyl chloride; sulfuric acid at 30℃; for 30h; | A 73% B 10.5% |
adamantane
1,3,5,7-tetrachloroadamanatane
Conditions | Yield |
---|---|
With tetrachloromethane; aluminium trichloride for 1h; Heating; | 98% |
With aluminum (III) chloride In tetrachloromethane Reflux; | 91% |
Conditions | Yield |
---|---|
With Rh(PPh3)3Cl In dichloromethane at 150℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With bromine; iron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 30℃; for 8h; | 97.3% |
With bromine; iron at 20℃; for 2h; Cooling with ice; | 96% |
With bromine at 0 - 25℃; | 85% |
Conditions | Yield |
---|---|
With nitrosonium tetrafluoroborate for 4h; reflux; | 97% |
With sulfuric acid at 3 - 25℃; for 5h; | 97% |
With bromine for 0.666667h; Ambient temperature; | 96% |
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% |
Molecular Structure:
Molecular Formula: C10H16
Molecular Weight: 136.24
CAS NO: 281-23-2
EINECS: 206-001-4
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 0 Å2
Index of Refraction: 1.517
Molar Refractivity: 42.22 cm3
Molar Volume: 139.4 cm3
Surface Tension: 34.4 dyne/cm
Density: 0.976 g/cm3
Flash Point: 48.9 °C
Enthalpy of Vaporization: 40.6 kJ/mol
Boiling Point: 187.1 °C at 760 mmHg
Vapour Pressure: 0.881 mmHg at 25°C
Melting Point: 209-212 °C (subl.)(lit.)
Stability: Stable. Combustible. Incompatible with strong oxidizing agents
Appearance: slightly beige crystals
IUPAC Name: Adamantane
Product Categories of Adamantane (CAS NO.281-23-2): Pharmaceutical Intermediates;Adamantane Derivative;Adamantane derivatives;Adamantanes;Alkanes;Cyclic;Organic Building Blocks
Adamantane (CAS NO.281-23-2) is used in some dry etching masks. Besises, it is also used in some polymer formulations.
In dye lasers, Adamantane may be used to extend the life of the gain medium.
Production of Adamantane (CAS NO.281-23-2):
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 10gm/kg (10000mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999. | |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999. | |
rat | LD50 | intraperitoneal | > 5gm/kg (5000mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999. | |
rat | LD50 | oral | > 10gm/kg (10000mg/kg) | Toksikologicheskii Vestnik. Vol. (4), Pg. 42, 1999. |
Safety Information about Adamantane (CAS NO.281-23-2):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36-26
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
Hazard Note: Irritant
HS Code: 29021990
The chemical synonyms of Adamantane (CAS NO.281-23-2): Adamantane (8CI) ; Tricyclo(3.3.1.13,7)decane
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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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