6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry; | 94% |
2-cyano-6-methoxynaphthalene
6-cyano-2-naphthol
Conditions | Yield |
---|---|
91% | |
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 10h; | 83% |
With boron tribromide In dichloromethane at -78 - 20℃; for 16h; Inert atmosphere; | 69% |
With sodium cyanide In dimethyl sulfoxide at 160 - 170℃; for 12h; | 62% |
With boron tribromide |
trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry; | 91% |
6-bromo-naphthalen-2-ol
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With CuCN In N,N-dimethyl-formamide at 160 - 170℃; for 3h; | 83% |
56% | |
In ethanol; N,N-dimethyl-formamide | |
In ethanol; N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 160 - 170℃; for 4h; Inert atmosphere; | 83% |
In N,N-dimethyl-formamide at 135℃; for 18h; | 62% |
In N,N-dimethyl-formamide at 150℃; | 60% |
6-hydroxynaphthalene-2-carbaldehyde
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 1h; | 70% |
6-acetoxy-[2]naphthonitrile
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With potassium hydroxide |
acetate of α,α,α',α'-tetrabromo-3,4-xylenol
acrylonitrile
A
6-cyano-2-naphthol
B
7-hydroxynaphthalene-2-carbonitrile
Conditions | Yield |
---|---|
1) NaI, DMF; 2) hydrolysis; Yield given. Multistep reaction. Title compound not separated from byproducts; |
benzoate of α,α,α',α'-tetrabromo-3,4-xylenol
acrylonitrile
A
6-cyano-2-naphthol
B
7-hydroxynaphthalene-2-carbonitrile
Conditions | Yield |
---|---|
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction; | |
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With pyridine; copper(II) sulfate In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With 1,3-dimethyl-2-imidazolidinone at 160℃; for 3h; Substitution; |
2-Bromo-6-methoxynaphthalene
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With boron tribromide demethylation; |
3,4-dimethylphenyl benzoate
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 91 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 12 h / Heating; Irradiation 2: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating 3: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme | |
Multi-step reaction with 2 steps 1: 88.5 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 25 h / Heating; Irradiation 2: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating 2: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme |
6-bromonaphthalen-2-yl acetate
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: copper (II)-sulfate; pyridine / 180 - 190 °C 2: methanol. KOH-solution View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride; CaCl2 In water |
Conditions | Yield |
---|---|
With perchloric acid In water at 25℃; for 10h; Kinetics; Concentration; |
β-naphthol
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: bromine / acetic acid 1.2: 3 h / Reflux 2.1: N,N-dimethyl-formamide / 4 h / 160 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; tin; bromine / 3 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 160 - 170 °C / Inert atmosphere View Scheme |
6-methoxy-3,4-dihydro-1(2H)-naphthalenone
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C 3.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 4.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 6.1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme |
6-Methoxy-2-hydroxymethylen-1-tetralon
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 3: toluene-4-sulfonic acid / toluene / 16 h / Reflux 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 5: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme |
1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 16 h / Reflux 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 3: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme |
6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 2: toluene-4-sulfonic acid / toluene / 16 h / Reflux 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 4: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme |
6-methoxy-3,4-dihydronaphthalene-2-carbonitrile
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 2: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme |
6-Hydroxy-2-naphthoic acid
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 70 °C 2.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C 3.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C 3.2: 16 h / 25 °C View Scheme |
6-hydroxynaphthalene-2-carboxamide
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Stage #1: 6-hydroxynaphthalene-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 0 - 25℃; for 0.5h; Stage #2: With pyridine In tetrahydrofuran at 25℃; for 16h; |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C 2.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C 2.2: 16 h / 25 °C View Scheme |
6-bromo-naphthalen-2-ol
4-cyanophenylboronic acid
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 8h; Suzuki-Miyaura Coupling; High pressure; Inert atmosphere; |
6-cyano-2-naphthol
6-(aminomethyl)naphthalen-2-ol
Conditions | Yield |
---|---|
With ammonia; hydrogen; nickel In methanol; water | 100% |
6-cyano-2-naphthol
D-cysteine hydrochloride
(S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 80℃; for 5h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 100% |
6-cyano-2-naphthol
4-Methylbenzyl bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 98% |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction; | 98% |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction; | 98% |
6-cyano-2-naphthol
4-methylphenylboronic acid
6-p-tolyl-2-naphthonitrile
Conditions | Yield |
---|---|
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 4-methylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With stannic bromide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere; | 97% |
trifluoromethylsulfonic anhydride
6-cyano-2-naphthol
trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 48h; | 95% |
With triethylamine In dichloromethane at 20℃; | 93% |
With pyridine In dichloromethane at 20℃; | 79.1% |
6-cyano-2-naphthol
2,5,8,11-tetraoxatridecan-13-ol tosylate
Conditions | Yield |
---|---|
With potassium hydroxide In 1,2-dimethoxyethane at 80℃; for 16h; Williamson etherification; | 95% |
6-cyano-2-naphthol
p-toluenesulfonyl chloride
6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 95% |
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 95% |
Stage #1: 6-cyano-2-naphthol With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 4h; | 90% |
With dmap; triethylamine In dichloromethane at 20℃; |
6-cyano-2-naphthol
4-methoxycarbonylphenylboronic acid
methyl 4-(2-cyanonaphthalen-6-yl)benzoate
Conditions | Yield |
---|---|
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 4-methoxycarbonylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere; | 95% |
6-cyano-2-naphthol
Diphenylphosphine oxide
6-(diphenylphosphoryl)-2-naphthonitrile
Conditions | Yield |
---|---|
Stage #1: 6-cyano-2-naphthol With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In acetonitrile at 100℃; for 3h; Inert atmosphere; Stage #2: Diphenylphosphine oxide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In acetonitrile at 100℃; for 18h; Inert atmosphere; | 95% |
6-cyano-2-naphthol
6-(difluoromethoxy)-2-naphthonitrile
Conditions | Yield |
---|---|
With sodium hydroxide; phenol In N,N-dimethyl-formamide at 75℃; for 4h; Sealed tube; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere; | 95% |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetonitrile for 12h; Williamson Ether Synthesis; Reflux; | 95% |
6-cyano-2-naphthol
methanesulfonyl chloride
6-cyanonaphthalen-2-yl methanesulfonate
Conditions | Yield |
---|---|
Stage #1: 6-cyano-2-naphthol With triethylamine In toluene at 0℃; for 0.166667h; Stage #2: methanesulfonyl chloride In toluene at 20℃; for 12h; | 93% |
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 70℃; for 4h; | 93% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 93% |
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis; | 93% |
With potassium carbonate In acetonitrile at 80℃; | 93% |
1-ethynyl-2-methylbenzene
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; toluene at 80℃; for 2h; Inert atmosphere; Schlenk technique; | 93% |
trifluorormethanesulfonic acid
6-cyano-2-naphthol
trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 93% |
Conditions | Yield |
---|---|
With phosphorous acid In water; 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; regioselective reaction; | 93% |
6-cyano-2-naphthol
5-bromo-6-hydroxy-2-naphthonitrile
Conditions | Yield |
---|---|
With bromine; acetic acid at 20℃; | 92% |
With bromine; acetic acid at 25℃; for 2.5h; | |
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere; | |
With pyridinium perbromide hydrobromide In acetonitrile at 0℃; | |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere; Schlenk technique; |
1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate
6-cyano-2-naphthol
Conditions | Yield |
---|---|
With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine In methanol at -20℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction; | 92% |
Stage #1: 1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate; 6-cyano-2-naphthol With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate In methanol for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In methanol for 24h; Inert atmosphere; | 90% |
6-cyano-2-naphthol
Conditions | Yield |
---|---|
Stage #1: 6-cyano-2-naphthol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) bis(trifluoromethanesulfonate) In acetic acid at 100℃; for 0.166667h; Stage #2: C10H9BrOS2 In acetic acid at 100℃; for 4h; chemoselective reaction; | 92% |
6-cyano-2-naphthol
bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride
6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere; | 91% |
Molecular Structure of 6-Cyano-2-Naphthol (CAS NO.52927-22-7):
Molecular Formula: C11H7NO
Molar mass: 169.17938g/mol
Density: 1.28 g/cm3
Flash Point: 185.5 °C
Melting point: 165.5-170.5 °C
Appearance: Brown Crystalline Solid
Boiling Point: 383.1 °C at 760 mmHg
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 33.02Å2
Index of Refraction: 1.692
Molar Refractivity: 50.4 cm3
Molar Volume: 131.5 cm3
Surface Tension: 64.7 dyne/cm
Enthalpy of Vaporization: 65.64 kJ/mol
Vapour Pressure: 2.04E-06 mmHg at 25°C
Product Categoriy: Aromatics and Nitrogen Compounds; Cyanides/Nitriles; Chalcones; Functional Materials
Hazard Codes: Xi
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
WGK Germany: 3
6-Cyano-2-Naphthol , with CAS number of 52927-22-7, can be called 6-Hydroxy-2-naphthalenecarbonitrile ; 2-Cyano-6-hydroxynaphthalene ; 2-Hydroxy-6-naphthonitrile . 6-Cyano-2-Naphthol (CAS NO.52927-22-7) is functional Material,and can be used for building blocks forliquid crystals.
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