Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol; hexane; acetonitrile for 15h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate In methanol; benzene at 40℃; for 18h; | 100% |
Stage #1: 1-bromo-2-methoxynaphthalene With palladium dichloride In water at 20℃; for 0.0333333h; Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.966667h; | 90% |
With boron nitride In methanol at 20℃; for 23h; | 84% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 99% |
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h; | 95% |
With potassium hydroxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 25℃; for 2h; Williamson synthesis; | 92% |
Conditions | Yield |
---|---|
at 180℃; for 1h; | 99% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In sulfolane at 220℃; for 0.166667h; | 97% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 220℃; for 0.166667h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With poly(ethylene glycol) 400; sodium carbonate at 110℃; for 8h; | 99% |
Stage #1: β-naphthol With potassium carbonate In acetone for 0.25h; Stage #2: dimethyl sulfate In acetone for 7h; Reflux; | 97% |
With potassium carbonate In acetone for 1h; Heating; | 93% |
2-methoxynaphthalene-1-boronic acid
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With CpPd(SIPr)Cl; potassium tert-butylate In isopropyl alcohol at 25℃; for 24h; Inert atmosphere; | 99% |
With C38H52Cl2N8O4Pd; 1-bromo-2-methoxynaphthalene; potassium carbonate In tetrahydrofuran at 75℃; |
Conditions | Yield |
---|---|
Stage #1: methanol; 2-bromonaphthalene With nickel(II) chloride hexahydrate; cadmium(II) sulphide; triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl acetamide for 0.00277778h; Schlenk technique; Sonication; Stage #2: In N,N-dimethyl acetamide at 20℃; Schlenk technique; Irradiation; | 99% |
Stage #1: methanol With lithium methanolate at 20℃; for 0.0833333h; Stage #2: 2-bromonaphthalene With copper(l) iodide at 20 - 80℃; Ullmann etherification; Sealed tube; | 95% |
With palladium diacetate; caesium carbonate; tert-butyl XPhos In toluene at 80℃; for 9h; | 90% |
With 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; palladium diacetate; caesium carbonate In toluene at 80℃; for 12h; | 67% |
With potassium tert-butylate; C11H21ClN2NiO; bis(pinacol)diborane In toluene at 25℃; for 24h; | 21% |
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With nickel(II) acetate tetrahydrate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h; | 98% |
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 96h; Autoclave; | 95% |
With sodium hydride; lithium iodide In tetrahydrofuran; mineral oil at 50℃; for 7h; Reagent/catalyst; Solvent; Temperature; Sealed tube; | 81% |
2-cyano-6-methoxynaphthalene
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri-n-butyl phosphite; chlorotriisopropylsilane In ethylcyclohexane at 130℃; for 15h; Inert atmosphere; | 98% |
With bis(1,5-cyclooctadiene)nickel (0); hydrogen; trimethylaluminum; tricyclohexylphosphine In toluene at 130℃; under 750.075 Torr; for 24h; Schlenk technique; | 73% |
With bis(acetylacetonate)nickel(II); 1,1,3,3-Tetramethyldisiloxane; trimethylaluminum; tricyclohexylphosphine In toluene at 130℃; for 24h; Inert atmosphere; | 70% |
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; ethanol; potassium hexamethylsilazane In toluene at 150℃; for 8h; Inert atmosphere; | 64% |
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 120℃; for 24h; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
In methanol for 0.33h; Methylation; | 95% |
Conditions | Yield |
---|---|
With diethylene glycol dimethyl ether; potassium carbonate at 155℃; for 6h; | 95% |
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel; | 87% |
Conditions | Yield |
---|---|
With rhodium(II) acetate; 1,3-bis-(diphenylphosphino)propane In toluene at 200℃; under 7500.75 Torr; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; Molecular sieve; | 95% |
Conditions | Yield |
---|---|
In toluene at 100℃; for 6h; | 95% |
1-iodo-2-methoxynapthalene
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With 9-N-methylamino-1-oxophenalene; potassium tert-butylate; potassium In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Glovebox; | 94% |
With caesium carbonate; hydroquinone; palladium diacetate In N,N-dimethyl acetamide at 125℃; for 48h; | 91% |
Stage #1: 1-iodo-2-methoxynapthalene With palladium dichloride In water at 20℃; for 0.0333333h; Stage #2: With 1,1,3,3-Tetramethyldisiloxane for 0.966667h; | 85% |
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide for 0.5h; Ambient temperature; | 92% |
With 18-crown-6 ether; potassium carbonate In acetone for 10h; Heating; | 69% |
Conditions | Yield |
---|---|
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction; | 92% |
2-(dimethyl-1,1’-dimethylethylsilyloxy)naphthalene
methyl iodide
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide for 12h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole In neat (no solvent) at 100℃; for 0.116667h; Microwave irradiation; Green chemistry; | 90% |
methanol
carbonic acid dimethyl ester
β-naphthol
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride at 120 - 160℃; | 90% |
phenyltrimethylammonium chloride
β-naphthol
A
2-Methoxynaphthalene
B
N,N-dimethyl-aniline
Conditions | Yield |
---|---|
With caesium carbonate In toluene for 2h; Heating; | A 89% B n/a |
α-naphthol
carbonic acid dimethyl ester
A
2-Methoxynaphthalene
B
1-Methoxynaphthalene
Conditions | Yield |
---|---|
With dimanganese decacarbonyl at 180℃; for 1h; | A 11% B 89% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; trifluoroacetic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 70℃; for 24h; | 88% |
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere; | 63% |
1-acetyl-2-methoxynaphthalene
A
2-Methoxynaphthalene
B
6-methoxy-2-acetylnaphthalene
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In nitromethane at 50℃; for 18h; Product distribution; | A 86% B 9% |
1-bromo-2-methoxynaphthalene
phenylboronic acid
A
2-Methoxynaphthalene
B
1-phenyl-2-methoxynaphthalene
Conditions | Yield |
---|---|
With potassium fluoride; o-(dicyclohexylphosphino)diisopropylbenzamide; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 80℃; for 24h; Suzuki cross-coupling; | A n/a B 86% |
1-bromo-6-methoxynaphthalene
tert-butylmagnesium chloride
A
2-Methoxynaphthalene
B
1-(tert-butyl)-6-methoxynaphthalene
Conditions | Yield |
---|---|
With 1.54H2O*Cl2Ni; 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate In tetrahydrofuran at -10℃; for 1.5h; Kumada coupling reaction; Inert atmosphere; | A 13 mg B 86% |
N,N,N-trimethyl-2-naphthalenaminium trifluoromethanesulfonate
potassium methanolate
2-Methoxynaphthalene
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique; | 85% |
2-Methoxynaphthalene
1-chloro-2-methoxynaphthalene
Conditions | Yield |
---|---|
With hydrogenchloride; 2-nitropropane; pyridine hydrochloride for 1h; Heating; | 100% |
With Nitroethane; pyridine hydrochloride for 2h; Heating; | 100% |
With Nitroethane; pyridine hydrochloride for 2h; Heating; | 100% |
Conditions | Yield |
---|---|
Stage #1: para-iodoanisole With methyllithium; zinc(II) chloride In tetrahydrofuran; diethyl ether at -78℃; for 2h; Stage #2: 2-Methoxynaphthalene With bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 20℃; for 12h; Negishi coupling reaction; Inert atmosphere; | 100% |
2-Methoxynaphthalene
neopentylmagnesium bromide
2-neopentyl-naphthalene
Conditions | Yield |
---|---|
With nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran; toluene at 20℃; for 18h; Inert atmosphere; Sealed tube; | 100% |
2-Methoxynaphthalene
sodium phenylsulfonate
(2-methoxynaphthalen-1-yl)(phenyl)sulfane
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80℃; for 6h; | 100% |
2-Methoxynaphthalene
1-iodo-2-methoxynapthalene
Conditions | Yield |
---|---|
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 0.5h; | 99% |
With dicloroiodoisocyanuric acid In acetonitrile at 20℃; for 0.0166667h; Darkness; regioselective reaction; | 99% |
With methyltriphenylphosphonium peroxydisulfate; iodine In acetonitrile for 0.4h; Heating; | 98% |
Conditions | Yield |
---|---|
With dimethylbromosulphonium bromide In tetrahydrofuran; water for 24h; Product distribution; Mechanism; Heating; other aromatic compounds, other reagents: bromodimethylsulfonium bromide/acetic acid, bromine, bromine/acetic acid, other solvents: acetonitrile, CCl4, other reaction temperature and time; | 99% |
With N-Bromosuccinimide In tetrachloromethane at 25℃; for 3h; Irradiation; | 99% |
With dimethylbromosulphonium bromide In tetrahydrofuran; water for 24h; Heating; other reagents: bromodimethylsulfonium bromide/acetic acid, bromine, bromine/acetic acid; | 99% |
2-Methoxynaphthalene
1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 0℃; for 0.166667h; | A n/a B 99% |
2-Methoxynaphthalene
1-(2,3,4,5,6-pentafluorophenylthio)-2,3,5,6-tetramethyl-4-oxocyclohexa-2,5-dienyl 2-chloroacetate
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -30 - 0℃; for 0.166667h; | 99% |
2-Methoxynaphthalene
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
2-phenylnaphthalene
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); cesium fluoride; tricyclohexylphosphine In toluene at 120℃; for 12h; | 99% |
With potassium phosphate; [(N,N,N',N'-tetramethylethylendiamine)NiCl(o-tolyl)]; cesium fluoride; tricyclohexylphosphine In toluene at 120℃; for 12h; Reagent/catalyst; Glovebox; Inert atmosphere; Sealed tube; | 98% |
With bis(1,5-cyclooctadiene)nickel (0); cesium fluoride; tricyclohexylphosphine In toluene at 120℃; for 12h; Suzuki-Miyaura coupling; | 93% |
1,1-Diphenylmethanol
2-Methoxynaphthalene
1-benzhydryl-2-methoxynaphthalene
Conditions | Yield |
---|---|
With silica gel supported sodium hydrogen sulfate In 1,2-dichloro-ethane at 30℃; for 0.5h; Friedel-Crafts type alkylation; | 99% |
With phosphomolybdic acid In acetonitrile at 20℃; for 0.5h; | 91% |
With pentafluorophenylboronic acid In 1,2-dichloro-ethane for 16h; Friedel-Crafts arylation; Reflux; Molecular sieve; | 87% |
Conditions | Yield |
---|---|
With triethylsilane; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 110℃; for 14h; Reagent/catalyst; Concentration; Solvent; | 99% |
With isopropylmagnesium bromide; nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran at 100℃; for 18h; Inert atmosphere; Sealed tube; | 70% |
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; sodium t-butanolate In toluene at 140℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 63% |
2-Methoxynaphthalene
para-methylphenylmagnesium bromide
2-(p-tolyl)naphthalene
Conditions | Yield |
---|---|
Stage #1: 2-Methoxynaphthalene With Ni(PCy3)(1,3-di-tert-butylimidazol-2-ylidene)Br2 In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Schlenk technique; Stage #2: para-methylphenylmagnesium bromide In tetrahydrofuran at 25℃; for 10h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 99% |
With bis(1,5-cyclooctadiene)nickel (0); magnesium; 1,3-di-tert-butylimidazol-2-ylidene In tetrahydrofuran at 60℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique; Green chemistry; | 99% |
With C68H72Cl2N6NiP2 In tetrahydrofuran at 25℃; for 24h; Inert atmosphere; | 95% |
2-Methoxynaphthalene
trimethylsilylmethyllithium
trimethyl(naphthalen-2-ylmethyl)silane
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0) In toluene; pentane at 50℃; for 2h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; | 76% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel(0); 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 80℃; for 14h; Inert atmosphere; Glovebox; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube; | 99% |
2-Methoxynaphthalene
Conditions | Yield |
---|---|
With C2F6NO4S2(1-)*C18H12F3P*Au(1+) In 1,2-dichloro-ethane at 20℃; for 0.25h; Molecular sieve; Heating; Inert atmosphere; | 99% |
With C20H12AuF9NO4PS2 In 1,2-dichloro-ethane at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Nicholas Reaction; Inert atmosphere; Molecular sieve; | 23.8 mg |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane at 0℃; for 1.2h; | 98.6% |
Conditions | Yield |
---|---|
With Zr6(μ3-O)4(μ3-OH)4(trimesic acid )2[triflate]6 at 25℃; for 2h; Catalytic behavior; Reagent/catalyst; Friedel-Crafts Acylation; | 98% |
With ZrOTfBTCSiO2 In dichloromethane at 25℃; for 2h; Reagent/catalyst; Temperature; Solvent; Friedel-Crafts Acylation; | 98% |
With aluminium dodecatungsten phosphate at 60 - 70℃; for 1.6h; | 91% |
Conditions | Yield |
---|---|
With hydrogen bromide; sodium bromide In chloroform; water at 0℃; Electrochemical reaction; | 98% |
With bromine; acetic acid at 55 - 85℃; under 760.051 Torr; for 0.275h; Temperature; | 90.2% |
With tin; bromine; acetic acid 2.) reflux; Multistep reaction; |
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran at 67℃; for 48h; | 98% |
With dimethylboron bromide In 1,2-dichloro-ethane at 70℃; for 36h; | 96% |
With boron trichloride; tetra-(n-butyl)ammonium iodide In dichloromethane at -78 - 0℃; for 1h; dealkylation; | 96% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In neat (no solvent) at 120℃; for 24h; Inert atmosphere; Sealed tube; | 98% |
With bismuth(lll) trifluoromethanesulfonate In water; 1,2-dichloro-ethane at 110℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
With aluminium trichloride In dichloromethane for 27.5h; Ambient temperature; | 81.3% |
Conditions | Yield |
---|---|
With aluminium dodecatungsten phosphate; trifluoroacetic anhydride at 20℃; for 2.5h; Friedel-Crafts acylation; | 98% |
With aluminium dodecatungsten phosphate; trifluoroacetic anhydride at 20℃; for 0.25h; | 98% |
With silica gel supported aluminium trichloride In 1,2-dichloro-ethane at 80℃; for 2.2h; Friedel Crafts acylation; regioselective reaction; | 91% |
With cross-linked polystyrene-supported aluminum triflate In 1,2-dichloro-ethane at 80℃; for 3.1h; Friedel-Crafts acylation; regioselective reaction; | 90% |
With trifluoromethylsulfonic anhydride In nitromethane at 20℃; for 0.0333333h; Friedel-Crafts acylation; | 87% |
The 2-Methoxynaphthalene is an organic compound with the formula C11H10O. The IUPAC name of this chemical is 2-methoxynaphthalene. With the CAS registry number 93-04-9, it is also named as Methyl 2-naphthyl ether. The product's categories are Food & Feed Additives; Naphthalene Derivatives. Besides, it is a white powder, which should be stored in a closed and cool place. It is used as a soap fragrance.
Physical properties about 2-Methoxynaphthalene are: (1)ACD/LogP: 3.36; (2)ACD/LogD (pH 5.5): 3.36; (3)ACD/LogD (pH 7.4): 3.36; (4)ACD/BCF (pH 5.5): 212.28; (5)ACD/BCF (pH 7.4): 212.28; (6)ACD/KOC (pH 5.5): 1611.41; (7)ACD/KOC (pH 7.4): 1611.41; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 9.23 Å2; (11)Index of Refraction: 1.604; (12)Molar Refractivity: 50.77 cm3; (13)Molar Volume: 147.5 cm3; (14)Polarizability: 20.12×10-24cm3; (15)Surface Tension: 38.5 dyne/cm; (16)Density: 1.072 g/cm3; (17)Flash Point: 102.3 °C; (18)Enthalpy of Vaporization: 48.97 kJ/mol; (19)Boiling Point: 272 °C at 760 mmHg; (20)Vapour Pressure: 0.0104 mmHg at 25°C.
Preparation: this chemical can be prepared by naphthalen-2-ol and iodomethane. This reaction will need reagent KOH and methanol.
Uses of 2-Methoxynaphthalene: it can be used to produce (1-iodo-[2]naphthyl)-methyl ether by heating. It will need reagent N-iodosuccinimide and solvent acetonitrile with reaction time of 30 hours. The yield is about 89%.
You can still convert the following datas into molecular structure:
(1)SMILES: O(c2ccc1c(cccc1)c2)C
(2)InChI: InChI=1/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3
(3)InChIKey: LUZDYPLAQQGJEA-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3
(5)Std. InChIKey: LUZDYPLAQQGJEA-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 885, 1975. | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 885, 1975. |
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