2,5-dichloro-2,5-dimethyl hexane
toluene
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With aluminium trichloride for 12h; Heating; | 99% |
With aluminium trichloride In dichloromethane at 20℃; Friedel-Crafts alkylation; | 99% |
With aluminium trichloride In dichloromethane Friedel-Crafts alkylation; Heating; | 97% |
2,5-dichloro-2,5-dimethyl hexane
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With aluminum (III) chloride In toluene for 0.416667h; | 97% |
1,1,4,4,6-pentamethyl-1,4-dihydronaphthalene
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethyl acetate for 1h; | 80% |
Conditions | Yield |
---|---|
Stage #1: 2,5-dimethyl-2,5-hexanediol With hydrogenchloride In water at 20℃; for 1h; Stage #2: toluene With aluminum (III) chloride In dichloromethane at 20℃; for 3h; | 76% |
5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalene-1-carbaldehyde
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With Wilkinson's catalyst In toluene Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl conc. / 3 h / 20 °C 2: 99 percent / AlCl3 / CH2Cl2 / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 56 percent / HCl gas / ethanol 2: 91 percent / AlCl3 / CH2Cl2 / 1.) RT, 30 min, 2.) reflux, 15 min View Scheme | |
Multi-step reaction with 2 steps 1: conc. HCl, HCl gas / 0.25 h / 0 °C 2: 80.4 percent / AlCl3 / 1 h / 0 °C View Scheme |
1,1,4,4,7-pentamethyl-2-oxo-1,2,3,4-tetrahydronaphthalene
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 2: 79 percent / POCl3, pyridine / 100 °C 3: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme |
2,2,5,5-tetramethyltetrahydro-3-oxofuran
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 45 percent / AlCl3 / 2 h / 0 - 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 79 percent / POCl3, pyridine / 100 °C 4: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 45 percent / AlCl3 / 2 h / 0 - 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 1 h / Heating 3: 79 percent / POCl3, pyridine / 100 °C 4: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme |
1,1,4,4,7-pentamethyl-2-hydroxy-1,2,3,4-tetrahydronaphthalene
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 79 percent / POCl3, pyridine / 100 °C 2: 80 percent / H2 / 10percent Pd/C / ethyl acetate / 1 h View Scheme |
1,2,3,4-tetrahydro-1,1,4,4,5,7-hexamethylnaphthalene
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) NBS, 2.) 1-methylpyrrolidin-2-one, 3.) PCC / 1.) CCl4, 77 deg C, 45 min, 2.) H2O, 100 h, 1h, 3.) CH2Cl2, 20 deg C, 2 h 2: 3)3> / toluene / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) H2SO4, 2.) Mg, 4.) H2SO4 / 1.) 20 deg C, 3 h, 2.) THF, 75 deg C, 30 min, 3.) THF, reflux, 30 min, 4.) petroleum ether, 5 - 10 deg C, 30 min 2: 1.) NBS, 2.) 1-methylpyrrolidin-2-one, 3.) PCC / 1.) CCl4, 77 deg C, 45 min, 2.) H2O, 100 h, 1h, 3.) CH2Cl2, 20 deg C, 2 h 3: 3)3> / toluene / Heating View Scheme |
2,5-dichloro-2,5-dimethyl hexane
4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With hydrogenchloride; AlCl3 In toluene |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
acetyl chloride
1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalenyl)ethanone
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 1h; Ambient temperature; | 99% |
aluminium trichloride In 1,2-dichloro-ethane | 99% |
With aluminum (III) chloride In dichloromethane for 5h; Inert atmosphere; Reflux; | 96% |
methyl 5-(chloromethyl)-2-furoate
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
A
5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-N'-(2,4,6-trimethoxybenzyl)-2-furohydrazide
B
5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; aluminium trichloride In methanol; dichloromethane; water; ethyl acetate | A 99% B n/a |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
3-(methoxycarbonyl)benzoyl chloride
Conditions | Yield |
---|---|
With aluminum (III) chloride Friedel Crafts Acylation; | 98% |
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature; | 80% |
With aluminum (III) chloride In dichloromethane at 20℃; Friedel Crafts acylation; Reflux; | 2.21 g |
Monomethyl terephthalate
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
Conditions | Yield |
---|---|
With aluminum (III) chloride; thionyl chloride In dichloromethane at 20℃; for 4h; Temperature; Solvent; Reflux; | 95.3% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
4-methoxy-benzoyl chloride
(4-methoxy-phenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane | 95% |
With aluminium trichloride Friedel-Crafts acylation; | 70% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
phthalic monoacid monomethyl ester chloride
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature; | 91% |
4-chlorosulfonylbenzoyl chloride
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h; Friedel-Crafts Acylation; | 86% |
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h; | 2.3592 g |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
potassium p-carboxybenzenesulfonate
Conditions | Yield |
---|---|
Stage #1: potassium p-carboxybenzenesulfonate With thionyl chloride; N,N-dimethyl-formamide at 85℃; for 1.66667h; Stage #2: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h; | 86% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
2-bromo-3-methyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene
Conditions | Yield |
---|---|
With aluminium trichloride; bromine In dichloromethane | 85% |
With bromine In tetrachloromethane for 0.25h; Ambient temperature; | 80% |
With bromine In chloroform at 20℃; for 0.5h; | 60% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
4-Methoxycarbonylbenzoyl chloride
methyl 4-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>benzoate
Conditions | Yield |
---|---|
With aluminum (III) chloride Friedel Crafts Acylation; | 82% |
With iron(III) chloride In 1,2-dichloro-ethane at 75℃; for 16h; Friedel-Crafts acylation; | 81% |
With aluminium trichloride In dichloromethane for 0.25h; Heating; | 72% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxaldehyde
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; acetic acid In water at 100℃; for 1h; | 78% |
With ammonium cerium(IV) nitrate In acetic acid at 20℃; for 1h; | 78% |
With ammonium cerium (IV) nitrate; acetic acid at 100℃; for 1h; | 77% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
A
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxaldehyde
B
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic acid
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; acetic acid at 100℃; for 0.25h; | A 78% B 14% |
With ammonium cerium(IV) nitrate; acetic acid at 100℃; for 0.25h; | A 78% B 78% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-bromomethane
Conditions | Yield |
---|---|
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2.5h; Heating / reflux; | 72.5% |
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
1,1,4,4,6-pentamethyl-7-nitro-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With nitric acid; acetic anhydride | 72% |
With sulfuric acid; nitric acid at 20℃; for 4h; | 62.1% |
With sulfuric acid; nitric acid at -10℃; | 50% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
4-iodobenzoic acid chloride
2-(4-iodophenyl)-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-methanone
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; | 71% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 55℃; for 0.25h; | 70% |
methyl 5-(chloromethyl)-2-furoate
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
methyl 5-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)-methyl]-2-furoate
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane Friedel-Crafts alkylation; Heating; | 68% |
aluminum (III) chloride In dichloromethane for 2h; Heating / reflux; | 46% |
With aluminum (III) chloride In dichloromethane for 2h; Friedel Crafts Acylation; Heating / reflux; | 46% |
methyl 2-(chlorocarbonyl)pyrimidine-5-carboxylate
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
methyl 2-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]pyrimidine-5-carboxylate
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; Reflux; | 68% |
With aluminum (III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel-Crafts Acylation; Reflux; | 1.677 g |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxylic acid
Conditions | Yield |
---|---|
With potassium permanganate; sodium hydroxide In water; chlorobenzene at 100℃; for 16h; | 63.3% |
Stage #1: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With potassium permanganate; sodium hydroxide In pyridine; water at 95℃; for 16h; Stage #2: With hydrogenchloride In pyridine; water at 1℃; pH=1; | 57% |
With potassium permanganate Alkaline conditions; | 57% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
Stage #1: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene With 1,10-phenanthroline-5,6-dione; bathophenanthroline; silver trifluoromethanesulfonate; 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoromethanesulfonate); cesium fluoride at 20℃; for 0.0833333h; Glovebox; Sealed tube; Inert atmosphere; Stage #2: trifluoromethyl 4-fluorobenzene-1-sulfonate at 25℃; for 15h; Glovebox; Sealed tube; Inert atmosphere; | 59% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
1,2,3,4-tetrahydro-1,1,4,4,6-pentamethyl-5,7-dinitronaphthalene
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In 1,2-dichloro-ethane at 0℃; for 2h; | 57% |
With sulfuric acid; nitric acid |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
6-chlorocarbonyl-nicotinic acid methyl ester
methyl 6-<(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl>nicotinate
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; Reflux; | 54% |
With aluminium trichloride In dichloromethane for 0.166667h; Ambient temperature; | 50% |
With aluminium trichloride In nitromethane; dichloromethane at 15 - 30℃; for 24h; Friedel-Crafts acylation; | |
With aluminum (III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel-Crafts Acylation; Reflux; | 1.3 g |
5-carbethoxythiophene-2-carbonyl chloride
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
ethyl 5-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>thiophene-2-carboxylate
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane for 16h; Ambient temperature; | 50% |
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
benzoyl chloride
ethyl 5-<(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)carbonyl>thiophene-2-carboxylate
Conditions | Yield |
---|---|
aluminium trichloride In 1,2-dichloro-ethane | 50% |
4-(1,3,2-dioxaborinan-2-yl)benzoyl chloride
1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene
C22H27BO3
Conditions | Yield |
---|---|
With aluminum (III) chloride | 47% |
The Molecular Structure of 1,1,4,4,6-Pentamethyl-1,2,3,4-tetrahydronaphthalene (CAS NO.6683-48-3):
Empirical Formula: C15H22
Molecular Weight: 202.3352
Nominal Mass: 202 Da
Average Mass: 202.3352 Da
Monoisotopic Mass: 202.172151 Da
Index of Refraction: 1.491
Molar Refractivity: 66.5 cm3
Molar Volume: 229.3 cm3
Surface Tension: 30.1 dyne/cm
Density: 0.882 g/cm3
Flash Point: 112.5 °C
Enthalpy of Vaporization: 48.51 kJ/mol
Boiling Point: 267.4 °C at 760 mmHg
Melting Point: 31 °C
Vapour Pressure: 0.0134 mmHg at 25°C
IUPAC Name: 1,1,4,4,6-pentamethyl-2,3-dihydronaphthalene
Product Categories: Fused Ring Systems
Synonyms: 1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthalene ; 1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphthylene ; 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ; 1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphtalene ; 1,1,4,4,6-Pentamethyl-1,2,3,4- ; 1,2,3,4-Tetrahydro-1,1,4,4,6-pentamethylnaphtalene tech ; 1,1,4,4,6-Pentamethyltetralin ; 1,1,4,4,6-Pentamethyl-1,2,3,4-etrahydronaphthalene
Hazard Codes: Xi
Risk Statements: 20/21/22
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
Hazard Note: Irritant
HazardClass: IRRITANT
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