Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride at 90℃; for 1h; Solvent; Barton-McCombie Deoxygenation; Inert atmosphere; | 100% |
With decane; 2,2’-azobis(4-methoxy-2,4-dimethyl)valeronitrile; tri-n-butyl-tin hydride In toluene at 80℃; for 0.0166667h; | 99 % Chromat. |
Multi-step reaction with 2 steps 1: 98 percent / aq. HCl / dimethylformamide / 1.5 h 2: H2SO4 (91.5percent) / 72 h / Ambient temperature; var. of conc.of H2SO4, and var. of reaction time View Scheme |
1-bromo-3-methyladamantane
methylmagnesium bromide
A
1,3-dimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
In dibutyl ether at 85℃; | A 99% B 1% |
3,5-dimethyl-1-bromoadamantane
methylmagnesium bromide
A
1,3-dimethyladamantane
B
1,3,5-trimethyladamantane
Conditions | Yield |
---|---|
In dibutyl ether at 95℃; | A 2% B 98% |
Conditions | Yield |
---|---|
With aluminium trichloride at 69.85℃; for 50h; | 90% |
With hydrogen fluoride; boron trifluoride Temperature; Autoclave; | 75% |
With Y-zeolite(Na/H 0.97) In hexane at 300℃; for 10h; Concentration; Temperature; Time; Autoclave; Sealed tube; | 65% |
adamantane
methyl iodide
A
1,3-dimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With Rh(PPh3)3Cl In dichloromethane at 150℃; for 3h; | A 79% B 21% |
Conditions | Yield |
---|---|
With hydrogen fluoride; boron trifluoride at 100℃; for 4h; Temperature; Autoclave; | A 77% B 15% |
(3,5-dimethyl-adamantan-1-yl)-methanol
1,3-dimethyladamantane
Conditions | Yield |
---|---|
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; | 69% |
(1α,4α,4aβ,5α,8α,8aβ)-decahydro-1,4:5,8-dimethanonaphthalene
A
1,3-dimethyladamantane
B
1-ethyladamantane
C
1,4-dimethyladamantane
Conditions | Yield |
---|---|
With Y-zeolite(Na/H 0.97) In hexane at 300℃; for 10h; Autoclave; Sealed tube; | A 67% B 6% C 22% |
1,3-dibromoadamantane
methylmagnesium bromide
A
1,3-dimethyladamantane
B
adamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
In dibutyl ether at 140℃; | A 52% B 4% C 44% |
1,3-dibromoadamantane
methylmagnesium bromide
A
1,3-dimethyladamantane
B
adamantane
C
1-bromo-3-methyladamantane
Conditions | Yield |
---|---|
In dibutyl ether at 140℃; | A 52% B 4% C 44% |
1,3-dibromoadamantane
A
1,3-dimethyladamantane
B
adamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With methylmagnesium bromide In dibutyl ether at 140℃; | A 52% B 4% C 44% |
(1α,4α,4aβ,5α,8α,8aβ)-decahydro-1,4:5,8-dimethanonaphthalene
A
1,3-dimethyladamantane
B
1,2-dimethyladamantane
C
1-ethyladamantane
D
1,4-dimethyladamantane
Conditions | Yield |
---|---|
With Y-zeolite(Na/H 0.4) In hexane at 300℃; for 30h; Concentration; Time; | A 49% B 9% C 11% D 24% |
With Y-zeolite(Na/H 0.4) In hexane at 300℃; for 10h; Concentration; Time; | A 18% B 8% C 10% D 21% |
tetramethylsilane
1-adamanthanol
A
1,3-dimethyladamantane
B
adamantane
C
1,3,5,7-tetramethyladamantane
D
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 5h; Product distribution; other time;; | A 33% B n/a C 10% D 29% E 13% |
tetramethylsilane
1-adamanthanol
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 5h; | A 33% B 10% C 29% D 13% |
With aluminum tri-bromide |
ethyl-cyclohexane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
trans-Decalin
D
1-ethyladamantane
E
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride; tertiary butyl chloride at 160℃; for 15h; Product distribution; | A 18.76% B 6.3% C 1.25% D 3.46% E 15.01% F 2.76% |
methyl cyclohexane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
trans-Decalin
D
1-ethyladamantane
E
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride; tertiary butyl chloride at 160℃; for 15h; Product distribution; | A 10.78% B 7.79% C 4.7% D 4.25% E 17.49% F 1.5% |
(1α,4α,4aβ,5α,8α,8aβ)-decahydro-1,4:5,8-dimethanonaphthalene
A
1,3-dimethyladamantane
B
1,4-dimethyladamantane
Conditions | Yield |
---|---|
With Y-zeolite(Na/H 0.4) In hexane at 300℃; for 10h; Concentration; Time; | A 17% B 15% |
With Y-zeolite(Na/H 0.97) In hexane at 300℃; for 30h; Concentration; Time; | A 6% B 9% |
(1-methylethyl)-cyclohexane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
trans-Decalin
D
1-ethyladamantane
E
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride; tertiary butyl chloride at 160℃; for 15h; Product distribution; | A 8.98% B 7.37% C 7.47% D 2.04% E 13.24% F 1.59% |
isobutylcyclohexane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
trans-Decalin
D
1-ethyladamantane
E
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride; tertiary butyl chloride at 160℃; for 15h; Product distribution; | A 8.23% B 8.26% C 9.82% D 0.59% E 10.13% F 1.33% |
1-Adamantyl bromide
tetramethylsilane
A
1,3-dimethyladamantane
B
adamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 20℃; for 0.166667h; Further byproducts given; | A 32 % Chromat. B 21 % Chromat. C 39 % Chromat. |
With aluminum tri-bromide In dichloromethane at 20℃; for 1h; Further byproducts given; | A 35 % Chromat. B 13 % Chromat. C 37 % Chromat. |
1-Adamantyl bromide
tetramethylsilane
A
1,3-dimethyladamantane
B
adamantane
C
1,3,5,7-tetramethyladamantane
D
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 0.166667h; Product distribution; other time; various ratios of the educts and AlBr3; AlCl3 instead AlBr3; |
1-Adamantyl bromide
tetramethylsilane
A
1,3-dimethyladamantane
B
adamantane
C
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 20℃; for 0.166667h; Yield given. Yields of byproduct given; |
1-Adamantyl bromide
tetramethylsilane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given; | |
With aluminum tri-bromide In dichloromethane at 40℃; for 1.5h; Yield given. Further byproducts given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With magnesium 1.) n-butyl ether, 2.) n-butyl ether, 70 deg C; Yield given. Multistep reaction; |
tetramethylsilane
1-chloroadamantane
A
1,3-dimethyladamantane
B
adamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 0.166667h; Further byproducts given; | A 37 % Chromat. B 12 % Chromat. C 38 % Chromat. |
With aluminum tri-bromide In dichloromethane at 20℃; for 1h; Further byproducts given; | A 35 % Chromat. B 12 % Chromat. C 34 % Chromat. |
tetramethylsilane
1-chloroadamantane
A
1,3-dimethyladamantane
B
adamantane
C
1,3,5,7-tetramethyladamantane
D
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 0.166667h; Product distribution; other time; various ratios of the educts and AlBr3; |
tetramethylsilane
1-chloroadamantane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 0.166667h; Yield given. Further byproducts given. Yields of byproduct given; | |
With aluminum tri-bromide In dichloromethane at 20℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given; |
tetramethylsilane
adamantane
A
1,3-dimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 3h; Yield given. Yields of byproduct given; |
tetramethylsilane
adamantane
A
1,3-dimethyladamantane
B
1,3,5,7-tetramethyladamantane
C
1,3,5-trimethyladamantane
1-methyl-adamantane
E
1,3,5-Trimethyl-7-ethyladamantane
F
1,2,3,5,7-pentamethyladamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 6h; Product distribution; other time; other temperature; AlCl3 instead AlBr3; |
tetramethylsilane
adamantane
A
1,3-dimethyladamantane
B
1,3,5-trimethyladamantane
1-methyl-adamantane
Conditions | Yield |
---|---|
With aluminum tri-bromide In dichloromethane at 20℃; for 6h; Yield given. Yields of byproduct given; |
1,3-dimethyladamantane
Conditions | Yield |
---|---|
With aluminum (III) chloride; phosphorus trichloride for 5h; Inert atmosphere; Reflux; | 99% |
1,3-dimethyladamantane
formamide
1-formamido-3,5-dimethyltricyclo[3.3.1.13,7]decane
Conditions | Yield |
---|---|
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 20 - 25℃; for 6.5h; Stage #2: formamide at 30 - 35℃; for 3h; | 96.96% |
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 0 - 5℃; Stage #2: formamide at 55 - 60℃; for 2h; Stage #3: With ammonia In dichloromethane; water at 0 - 25℃; | 95% |
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 0℃; for 6h; Stage #2: formamide at 0 - 20℃; for 2.5h; Ritter-type reaction; Further stages.; | 89% |
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 0℃; Stage #2: formamide at 0 - 20℃; | 89.3% |
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 0℃; Stage #2: formamide at 0 - 20℃; for 2h; |
Conditions | Yield |
---|---|
Stage #1: 1,3-dimethyladamantane; trifluoroacetic acid With oxygen; sodium nitrite at 20℃; for 3h; Stage #2: With hydrogenchloride Further stages.; | 96% |
Conditions | Yield |
---|---|
In benzene at 23℃; Kinetics; | 96% |
Conditions | Yield |
---|---|
With water; bromine at 25℃; Reflux; | 95% |
With oxygen; cobalt acetylacetonate In acetic acid at 80℃; under 760.051 Torr; for 15h; | 90% |
With water; bromine for 2h; Ambient temperature; | 87% |
1,3-dimethyladamantane
bis(3,5-dimethyl-1-adamantyl)phosphinic chloride
Conditions | Yield |
---|---|
With aluminium trichloride; phosphorus trichloride at 75 - 85℃; for 5h; | 94.7% |
N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide
1,3-dimethyladamantane
(S)-N-[[(3,5-dimethyl-1-adamantyl)amino](4-tolyl)oxido-λ4-sulfanylidene]tosylamide
Conditions | Yield |
---|---|
With dirhodium tetrakis{(2S)-2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoic acid}; bis(tertbutylcarbonyloxy)iodobenzene In methanol; 1,2-dichloro-ethane at -35℃; for 72h; Molecular sieve; diastereoselective reaction; | 94% |
Conditions | Yield |
---|---|
With aluminum (III) chloride; bromine In 1,2-dichloro-ethane at 15℃; Reagent/catalyst; Temperature; Solvent; | 92% |
With bromine for 12h; Reflux; | 91.5% |
With iron(III)-acetylacetonate; carbon tetrabromide at 150℃; for 3h; Sealed tube; Inert atmosphere; | 85% |
2-amino-3-pyridinecarbonitrile
1,3-dimethyladamantane
2-(((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)amino)nicotinonitrile
Conditions | Yield |
---|---|
With aluminum tri-bromide; carbon tetrabromide In neat (no solvent) at 15 - 20℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 92% |
1,3-dimethyladamantane
acetonitrile
1,3‑diacetamido‑5,7‑dimethyladamantane
Conditions | Yield |
---|---|
Stage #1: 1,3-dimethyladamantane With nitric acid at 25℃; for 1h; Stage #2: acetonitrile for 0.5h; Stage #3: acetonitrile With sulfuric acid at 20℃; for 4h; Ritter Amidation; | 92% |
Trifluoromethanesulfonamide
1,3-dimethyladamantane
N-((1,3,5,7)-3,5-dimethyladamantan-1-yl)-1,1,1-trifluoromethanesulfonamide
Conditions | Yield |
---|---|
With bis(4-bromobenzoyloxy)iodobenzene; iodine In dichloromethane at 20℃; for 14h; Schlenk technique; Inert atmosphere; Irradiation; | 92% |
methanol
1,3-dimethyladamantane
carbon monoxide
dimethyl 5,7-dimethyladamantane-1,3-dicarboxylate
Conditions | Yield |
---|---|
Stage #1: 1,3-dimethyladamantane; carbon monoxide With Al2Br7(1-)*CBr3(1+) In 1,2-dibromomethane at 0℃; under 760.051 Torr; for 3h; Stage #2: methanol In 1,2-dibromomethane at 0 - 20℃; chemoselective reaction; | 91% |
1,3-dimethyladamantane
3,5-dimethyladamantan-1-yl nitrate
Conditions | Yield |
---|---|
With nitric acid at 10℃; | 90.3% |
With nitric acid In acetic acid at 20℃; for 1h; | |
With nitric acid for 3h; Cooling; | |
With nitric acid In acetic acid at 15 - 20℃; for 1h; |
Conditions | Yield |
---|---|
Stage #1: 1,3-dimethyladamantane With sulfuric acid; nitric acid at 0℃; for 6h; Stage #2: acetonitrile at 0 - 20℃; for 3.5h; Ritter-type reaction; Further stages.; | 90.3% |
With sulfuric acid In tert-butyl alcohol at 60 - 65℃; for 18h; Ritter Amidation; Large scale; | 90% |
With sulfuric acid at 60 - 80℃; for 10h; Ritter Amidation; | 73.5% |
1,3-dimethyladamantane
1,3‑dibromo‑5,7‑dimethyladamantane
Conditions | Yield |
---|---|
With bromine; iron In 1,2-dichloro-ethane at 25℃; Temperature; Reagent/catalyst; Solvent; | 90% |
With bromine; iron at 20℃; for 1.5h; Bromination; | 83% |
formic acid
1,3-dimethyladamantane
5,7-dimethyl-1,3-adamantanedicarboxylic acid
Conditions | Yield |
---|---|
With sulfuric acid at 20 - 28℃; for 5h; | 90% |
1,2,3-Benzotriazole
1,3-dimethyladamantane
1-((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)-1H-benzo[d][1,2,3]triazole
Conditions | Yield |
---|---|
With aluminum tri-bromide; carbon tetrabromide In neat (no solvent) at 15 - 20℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 89% |
1,3-dimethyladamantane
anthranilic acid nitrile
2-(((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)amino)benzonitrile
Conditions | Yield |
---|---|
With aluminum tri-bromide; carbon tetrabromide In neat (no solvent) at 15 - 20℃; for 0.0833333h; Green chemistry; chemoselective reaction; | 87% |
maleic anhydride
1,3-dimethyladamantane
3-(3,5-Dimethyl-adamantan-1-yl)-dihydro-furan-2,5-dione
Conditions | Yield |
---|---|
With di-tert-butyl peroxide In chlorobenzene at 150℃; for 5h; | 86% |
1,3-dimethyladamantane
1,3-difluoro-5,7-dimethyladamantane
Conditions | Yield |
---|---|
With iodine pentafluoride In 1,2-dichloro-ethane at 80℃; for 12h; regioselective reaction; | 86% |
1,3-dimethyladamantane
urethane
1-ethoxycarbonylamino-3,5-dimethyladamantane
Conditions | Yield |
---|---|
With nitric acid at 30℃; for 1h; | 85% |
With nitric acid 1.) 25 deg C, 15 min, 2.) RT, 1 h; Yield given. Multistep reaction; |
1,3-dimethyladamantane
1-fluoro-3,5-dimethyladamantane
Conditions | Yield |
---|---|
With iodine pentafluoride In dichloromethane at 10℃; for 12h; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate for 2h; | 85% |
N-[(1S)-amino(4-tolyl)oxido-λ4-sulfanylidene]tosylamide
1,3-dimethyladamantane
Conditions | Yield |
---|---|
With Rh2(S-N-(1,8-naphthoyl)alanine)4; bis(tertbutylcarbonyloxy)iodobenzene In methanol; 1,1,2,2-tetrachloroethane at -78 - -35℃; for 72h; Molecular sieve; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate for 2.5h; | 81% |
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate for 2.5h; | 80% |
Molecular Structure:
Molecular Formula: C12H20
Molecular Weight: 164.29
CAS NO: 702-79-4
EINECS: 211-870-8
H bond acceptors: 0
H bond donors: 0
Freely Rotating Bonds: 0
Polar Surface Area: 0 Å2
Index of Refraction: 1.52
Molar Refractivity: 51.44 cm3
Molar Volume: 168.9 cm3
Surface Tension: 39.1 dyne/cm
Density: 0.972 g/cm3
Flash Point: 52.8 °C
Enthalpy of Vaporization: 41.83 kJ/mol
Boiling Point: 199.9 °C at 760 mmHg
Vapour Pressure: 0.472 mmHg at 25°C
Melting Point: -30 °C
Stability: Stable. Incompatible with strong oxidizing agents. Flammable
Appearance: clear colourless liquid
IUPAC Name: 1,3-Dimethyladamantane
The chemical synonyms of 1,3-Dimethyladamantane (CAS NO.702-79-4): 1,3-Dimethyltricyclo(3.3.1.13,7)decane
Product Categories: Chemical intermediate for Memantine HCl;Adamantane derivatives;Adamantanes;Alkanes;Cyclic;Organic Building Blocks
1,3-Dimethyladamantane (CAS NO.702-79-4):
Hazard Codes: F
Risk Statements: 10
R10:Flammable.
Safety Statements: 16
S16:Keep away from sources of ignition.
RIDADR UN: 1993 3/PG 3
WGK Germany: 3
HazardClass: 3
PackingGroup: III
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