2-Bromo-6-methoxynaphthalene
N,N-dimethyl-formamide
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; | 97% |
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran Stage #2: N,N-dimethyl-formamide | 90% |
Stage #1: 2-Bromo-6-methoxynaphthalene With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 0.25h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; cyclohexane at -78℃; for 0.25h; Further stages.; | 74% |
(6-methoxy-2-naphthyl)methanol
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating; | 95% |
With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide In water at 20℃; for 2h; Green chemistry; chemoselective reaction; | 95% |
With pyridinium chlorochromate In dichloromethane at 20℃; |
(6-methoxynaphthalene-2-yl)methyl acetate
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating; | 95% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 0.6h; oxidative cleavage; | 94% |
carbon monoxide
2-Bromo-6-methoxynaphthalene
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; propyl di-tert-butylphosphinite In toluene at 100℃; under 3750.38 Torr; for 20h; Inert atmosphere; | 93% |
With N,N,N,N,-tetramethylethylenediamine; hydrogen; palladium diacetate; catacxium A In toluene at 120℃; under 9000.9 Torr; Flow reactor; Green chemistry; | 84% |
With 4-methoxy-N'-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.3 Torr; for 16h; | 99 % Chromat. |
With N,N,N,N,-tetramethylethylenediamine; hydrogen; catacxium A; palladium diacetate In toluene at 100℃; under 3750.38 Torr; for 16h; | 99 % Chromat. |
2-methyl-6-methoxynaphthalene
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 5h; Heating; | 90% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating; | 90% |
Conditions | Yield |
---|---|
With pyridine; 1,3-bis-(diphenylphosphino)propane; hydrogen; palladium diacetate In dimethyl sulfoxide at 120℃; under 7500.75 Torr; for 2h; Flow reactor; | 90% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; N,N-dimethyl-formamide at -78 - 20℃; for 2h; Inert atmosphere; | 88.6% |
With n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide | |
With magnesium; acetic acid In tetrahydrofuran; N,N-dimethyl-formamide |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With (Bu4N)2S2O8 In 1,2-dichloro-ethane for 1.5h; Heating; | 87.5% |
formaldehyd
2-Bromo-6-methoxynaphthalene
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With triethylsilane; dichloro bis(acetonitrile) palladium(II); sodium carbonate; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 20 - 100℃; under 15001.5 Torr; for 20h; Inert atmosphere; Autoclave; | 61% |
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; acetic acid for 4h; Heating; | 50% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With copper(II) acetate monohydrate In ethanol; water at 60℃; for 5h; | 40% |
2-cyano-6-methoxynaphthalene
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In n-heptane; toluene at -40℃; for 1h; | 22% |
methyl 6-methoxy-2-naphthylacetate
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With oxygen In acetonitrile for 0.25h; Oxidation; decarboxylation; Irradiation; | 2% |
6-methoxy-2-naphthoyl chloride
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With quinoline; Pd-BaSO4; sulfur Hydrogenation.Reagens 4:Xylol; |
(E)-2-methoxy-6-(prop-1-en-1-yl)naphthalene
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With osmium(VIII) oxide; periodic acid |
N-benzenesulfonyl-N'-(6-methoxy-[2]naphthoyl)-hydrazine
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium carbonate; ethylene glycol |
6-methoxynaphthalen-2-ylmagnesium bromide
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With tetrahydrofuran; N,N-dimethyl-formamide |
6-methoxynaphthalen-2-ylmagnesium bromide
orthoformic acid triethyl ester
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With diethyl ether; benzene Erhitzen des nach dem Eindampfen erhaltenen Rueckstands auf 100grad und anschlissendes Behandeln mit Eis und Essigsaeure; |
6-methoxy-2-naphthylacetic acid
A
6-methoxynaphthalene-2-carbaldehyde
B
(6-methoxy-2-naphthyl)methanol
Conditions | Yield |
---|---|
With oxygen In phosphate buffer for 0.25h; Product distribution; Further Variations:; Solvents; addition of CCl4; without O2; Oxidation; decarboxylation; Irradiation; |
(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone
A
6-methoxynaphthalene-2-carbaldehyde
B
acetone
Conditions | Yield |
---|---|
With phosphate buffer; sodium chloride; antibody 93F3 from mice pH=7.4; Enzyme kinetics; Further Variations:; Catalysts; Kinetic resolution; Retro aldol reaction; |
Conditions | Yield |
---|---|
With phosophate buffer; antibody 93F3 from mice pH=7.7; Enzyme kinetics; Further Variations:; Catalysts; Kinetic resolution; Retro aldol reaction; |
(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone
A
6-methoxynaphthalene-2-carbaldehyde
B
acetone
Conditions | Yield |
---|---|
With aldolase antibody Fab 28 In dimethyl sulfoxide at 25℃; pH=7.4; Kinetics; Further Variations:; Reagents; retro-aldolization; Enzymatic reaction; | |
With YLK-18-opt peptide In phosphate buffer; acetonitrile at 25℃; pH=7.5; Enzyme kinetics; Further Variations:; Reagents; | |
With recombinant mutant Tyr78Phe RA61 retroaldolase; water In dimethyl sulfoxide at 25℃; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; | |
With C39H60N6O5 In aq. phosphate buffer pH=7.45; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent; |
Conditions | Yield |
---|---|
With aldolase antibody Fab 28 In dimethyl sulfoxide at 25℃; pH=7.4; Kinetics; Further Variations:; Reagents; retro-aldolization; Enzymatic reaction; |
Conditions | Yield |
---|---|
With aldolase antibody Fab 28 In dimethyl sulfoxide at 25℃; pH=7.4; Kinetics; Further Variations:; Reagents; retro-aldolization; Enzymatic reaction; |
Conditions | Yield |
---|---|
With YLK-18-opt peptide In phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.5; Enzyme kinetics; Further Variations:; Reagents; |
(R)-2-(6-methoxy-2-naphthyl)-1,2-epoxyethane
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium periodate; bovine serum albumin In phosphate buffer; N,N-dimethyl-formamide at 26℃; pH=7.2; Enzyme kinetics; Further Variations:; pH-values; |
(+/-)-2-(6-methoxy-2-naphthyl)-1,2-ethanediol
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium periodate; bovine serum albumin In phosphate buffer; N,N-dimethyl-formamide at 26℃; pH=7.2; Enzyme kinetics; Further Variations:; pH-values; |
(±)-4-hydroxy-4-(6-methoxy-2-naphthyl)-2-butanone
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With sodium phosphate In acetonitrile at 25℃; pH=7.5; Enzyme kinetics; | |
With mAb 38C2 | |
With monoclonal aldolase antibody 85H6 In ethanol retro-aldol reaction; aq. phosphate buffer; |
6-methoxynaphthalene-2-carbaldehyde
2-(3,4-dimethoxyphenyl)ethyl alcohol
3,4-dihydro-6,7-dimethoxy-1-(2-methoxynaphthalen-6-yl)-1H-isochromene
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction; | 99% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 80℃; for 4h; Inert atmosphere; | 99% |
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 6h; |
6-methoxynaphthalene-2-carbaldehyde
2-cyano-6-methoxynaphthalene
Conditions | Yield |
---|---|
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube; | 99% |
With oxygen; copper(ll) bromide; potassium hexacyanoferrate(III) In N,N-dimethyl-formamide at 150℃; for 12h; Sealed tube; | 73% |
Multi-step reaction with 2 steps 1: sodium acetate / methanol; water / 20 °C 2: bis[2-(diphenylphosphino)phenyl] ether; bis(1,5-cyclooctadiene)nickel (0) / tetrahydrofuran / 17 h / 60 °C View Scheme |
Conditions | Yield |
---|---|
In ethanol at 20℃; Alkaline conditions; | 99% |
With alkali hydroxide In ethanol at 20℃; | 99% |
6-methoxynaphthalene-2-carbaldehyde
(6-methoxy-2-naphthyl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 0.333333h; Inert atmosphere; | 98% |
With lithium aluminium tetrahydride | 95% |
With sodium tetrahydroborate In methanol; water for 2h; Ambient temperature; | 91.7% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,5-dimethylbenzyl triphenylphosphonium chloride With sodium methylate In methanol at 20℃; for 1.5h; Stage #2: 6-methoxynaphthalene-2-carbaldehyde In methanol for 36h; Further stages.; | 98% |
Conditions | Yield |
---|---|
Wells-Dawson heteropolyacid catalyst at 80℃; for 1.5h; Biginelli reaction; | 98% |
With polyvinylsulfonic acid In water at 90℃; for 1.66667h; Solvent; Temperature; Biginelli Pyrimidone Synthesis; Green chemistry; | 86% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane | 98% |
Conditions | Yield |
---|---|
With sodium azide; N,N,N,N,-tetramethylethylenediamine; copper(l) chloride In dimethyl sulfoxide at 120℃; for 12h; | 98% |
6-methoxynaphthalene-2-carbaldehyde
diisopropyl trimethylsily phosphite
Conditions | Yield |
---|---|
With 3,3’-bis[3,5-bis(perfluoropropan-2-yl)phenyl]-1,1’-binaphthalene-2,2’-sulfonimide In diethyl ether at -78℃; for 96h; Abramov Phosphorylation; enantioselective reaction; | 98% |
di-tert-butyl-diazodicarboxylate
6-methoxynaphthalene-2-carbaldehyde
3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Conditions | Yield |
---|---|
With benzoic acid In tetrahydrofuran at 20℃; for 24h; diastereoselective reaction; | 98% |
With benzoic acid In tetrahydrofuran at 20℃; for 24h; | 98% |
nitromethane
6-methoxynaphthalene-2-carbaldehyde
2-methoxy-6-(2-nitrovinyl)naphthalene
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 90 - 100℃; Aldol Condensation; | 97.4% |
With methylamine hydrochloride; sodium acetate In methanol at 20℃; for 2h; |
6-methoxynaphthalene-2-carbaldehyde
acetone
4-(2-methoxynaphthalene-6-yl)but-3-en-2-one
Conditions | Yield |
---|---|
With sodium hydroxide In water at 70℃; for 0.125h; Aldol condensation; Microwave irradiation; Continuous flow; | 97% |
With sodium hydroxide | |
With sodium hydroxide In water for 4h; Aldol Condensation; | |
With Nickel-Lanthanum-Magnesium mixed oxide on mesoporous silica at 140℃; for 6h; Reagent/catalyst; |
1,8-diaminooctan
6-methoxynaphthalene-2-carbaldehyde
N,N'-bis[(6-methoxynaphthalen-2-yl)methylene]octane-1,8-diamine
Conditions | Yield |
---|---|
In ethanol for 0.5h; Heating; | 97% |
6-methoxynaphthalene-2-carbaldehyde
1-triphenylphosphoranylidene-2-propanone
4-(2-methoxynaphthalene-6-yl)but-3-en-2-one
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 210℃; Wittig reaction; Continuous flow; | 97% |
6-methoxynaphthalene-2-carbaldehyde
Phenyl triflate
(6-methoxynaphthalen-2-yl)(phenyl)methanone
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)nickel (0); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 110℃; for 20h; Inert atmosphere; Sealed tube; | 97% |
1,10-phenanthroline-5,6-dione
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 180℃; for 0.25h; Microwave irradiation; | 97% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With magnesium sulfate; methylamine In ethanol; dichloromethane | 96% |
1,6-Hexanediamine
6-methoxynaphthalene-2-carbaldehyde
N,N'-bis[(6-methoxynaphthalen-2-yl)methylene]hexane-1,6-diamine
Conditions | Yield |
---|---|
In ethanol for 0.5h; Heating; | 96% |
Conditions | Yield |
---|---|
In methanol for 16h; Reflux; | 96% |
1-(isopropylsulfonyl)-3,5-bis(trifluoromethyl)benzene
6-methoxynaphthalene-2-carbaldehyde
2-methoxy-6-(2-methylprop-1-en-1-yl)naphthalene
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In tetrahydrofuran; hexane at 20℃; Julia-Kocienski olefination; | 95% |
Conditions | Yield |
---|---|
With rhodium(II) acetate; 1,3-bis-(diphenylphosphino)propane In toluene at 200℃; under 7500.75 Torr; Inert atmosphere; | 95% |
6-methoxynaphthalene-2-carbaldehyde
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 20℃; for 12h; | 95% |
6-methoxynaphthalene-2-carbaldehyde
methyl (triphenylphosphoranylidene)acetate
Conditions | Yield |
---|---|
Stage #1: 6-methoxynaphthalene-2-carbaldehyde; methyl (triphenylphosphoranylidene)acetate In dichloromethane at 20℃; for 24h; Inert atmosphere; Stage #2: With methanol; sodium hydride In tetrahydrofuran at 55℃; for 6.5h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene Dean-Stark; Reflux; | 95% |
Conditions | Yield |
---|---|
Stage #1: tryptamine; 6-methoxynaphthalene-2-carbaldehyde In methanol at 20℃; for 4h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate at 0℃; for 1h; Inert atmosphere; | 95% |
The 6-Methoxy-2-Naphthaldehyde is an organic compound with the formula C12H10O2. The IUPAC name of this chemical is 6-methoxynaphthalene-2-carbaldehyde. With the CAS registry number 3453-33-6 and EINECS 222-377-2, it is also named as 2-naphthalenecarboxaldehyde, 6-methoxy-. The product's categories are Aromatic Aldehydes & Derivatives (substituted); Aldehydes; C10 to C21; Carbonyl Compounds. It is slightly yellow crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
Physical properties about 6-Methoxy-2-Naphthaldehyde are: (1)ACD/LogP: 2.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.63; (4)ACD/LogD (pH 7.4): 2.63; (5)ACD/BCF (pH 5.5): 58.72 ; (6)ACD/BCF (pH 7.4): 58.72; (7)ACD/KOC (pH 5.5): 642.26; (8)ACD/KOC (pH 7.4): 642.26; (9)#H bond acceptors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.642 ; (12)Molar Refractivity: 57.527 cm3; (13)Molar Volume: 159.218 cm3; (14)Polarizability: 22.805 10-24cm3; (15)Surface Tension: 45.2000007629395 dyne/cm; (16)Density: 1.17 g/cm3; (17)Flash Point: 162.74 °C; (18)Enthalpy of Vaporization: 58.375 kJ/mol; (19)Boiling Point: 340.216 °C at 760 mmHg
Preparation of 6-Methoxy-2-Naphthaldehyde: It can be obtained by methyl-(6-methyl-[2]naphthyl)-ether. This reaction needs reagent 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and solvents acetic acid, H2O by heating. The reaction time is 4.0 hours. The yield is 90%.
Uses of 6-Methoxy-2-Naphthaldehyde: It is used as intermediate of Nabumetone. It is also used for fluorometric assays for isozymes of human alcohol dehydrogenase. What's more, it can react with malonic acid diethyl ester to get (6-methoxy-[2]naphthylmethylene)-malonic acid diethyl ester. This reaction needs reagent piperidine, benzoic acid and solvent benzene by heating. The reaction time is 16 hours. The yield is 81%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin, so people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=Cc1ccc2c(c1)ccc(OC)c2
2. InChI:InChI=1/C12H10O2/c1-14-12-5-4-10-6-9(8-13)2-3-11(10)7-12/h2-8H,1H3
3. InChIKey:VZBLASFLFFMMCM-UHFFFAOYAL
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