3469-26-9

Usage

Uses

Used in Chemical Research:
2,7-Dimethoxynaphthalene is used as a matrix for investigating the structure of polymetallic porphyrins via matrix-assisted laser desorption/ionization (MALDI). This technique allows for the analysis of large biomolecules and provides valuable insights into their structure and properties.
Used in Organic Synthesis:
2,7-Dimethoxynaphthalene serves as a key intermediate in the synthesis of various organic compounds, such as peri-aroylnaphthalene compounds and 2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol. Its presence in these reactions contributes to the formation of complex molecular structures with potential applications in pharmaceuticals, materials science, and other industries.

InChI:InChI=1/C12H12O2/c1-13-11-5-3-9-4-6-12(14-2)8-10(9)7-11/h3-8H,1-2H3

Synthetic route

2,7-Dihydroxynaphthalene (582-17-2) + dimethyl sulfate (77-78-1) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With potassium carbonate In acetone for 10h; Reflux;	98.3%
With sodium hydroxide	97%
With sodium hydroxide for 2h;	96.5%

1-Iodo-2,7-dimethoxynaphthalene → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With 9-N-methylamino-1-oxophenalene; potassium tert-butylate; potassium In 1,4-dioxane; dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Glovebox;	93%

methanol (67-56-1) + 2,7-Dihydroxynaphthalene (582-17-2) → 2,7-Dimethoxynaphthalene (3469-26-9) + 7-methoxy-2-naphthol (5060-82-2)

Conditions	Yield
With hydrogenchloride for 72h; Ambient temperature;	A n/a B 71%

2,7-Dihydroxynaphthalene (582-17-2) + methyl iodide (74-88-4) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 20℃; for 24h;	68%
With methanol; potassium carbonate
With potassium carbonate In N,N-dimethyl-formamide at 50 - 60℃; under 46 Torr;

1-acetyl-2,6-dimethoxynaphthalene (71094-89-8) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With sulfuric acid at 20℃; for 0.666667h;	68%

1-acetyl-2,6-dimethoxynaphthalene (71094-89-8) → 2,7-Dimethoxynaphthalene (3469-26-9) + 3-methyl-4,9-dimethoxyphenalenone (53307-81-6) + 2-acetyl-3,6-dimethoxynaphthalene (86358-73-8)

Conditions	Yield
With PPA at 45℃; for 3.5h;	A 18% B 4% C 59%

dicyclopropyl ketone (1121-37-5) + 2,7-dimethoxynaphthalene radical anion → 2,7-Dimethoxynaphthalene (3469-26-9) + dicyclopropyl ketone radical anion

Conditions	Yield
In N,N-dimethyl-formamide Kinetics; Electrolysis;

2,7-Dihydroxynaphthalene (582-17-2) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
potassium carbonate; dimethyl sulfate In water; acetone

2,7-Dihydroxynaphthalene (582-17-2) + potassium carbonate (584-08-7) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With dimethyl sulfate In water; acetone

methyl bromide (74-83-9) + 2,7-Dihydroxynaphthalene (582-17-2) → 2,7-Dimethoxynaphthalene (3469-26-9)

Conditions	Yield
With potassium carbonate

2,7-Dimethoxynaphthalene (3469-26-9) + tert-butyl alcohol (75-65-0) → 2,7-di-t-butyl-3,6-dimethoxynaphthalene (274911-44-3)

Conditions	Yield
With sulfuric acid; trifluoroacetic acid at 45℃; for 46h; Alkylation;	99%

2,7-Dimethoxynaphthalene (3469-26-9) → 2,7-dimethoxy-1,4,5,8-tetrahydronaphthalene (1614-82-0)

Conditions	Yield
With ethanol; ammonia; lithium	98%
With ethanol; ammonia; lithium Birch reduction; Cooling with dry ice; Inert atmosphere;	93%
With ethanol; ammonia; lithium Birch reaction; Inert atmosphere; Cooling; Reflux;	93%
With ammonia; sodium In ethanol	91%
With ethanol; ammonia; sodium In tetrahydrofuran at -65℃; for 3h; Birch reduction;	74%

difluoromethyl phenyl sulfide (1535-67-7) + 2,7-Dimethoxynaphthalene (3469-26-9) → 2,7-dimethoxy-1-naphthalenecarbaldehyde (51385-93-4)

Conditions	Yield
Stage #1: difluoromethyl phenyl sulfide; 2,7-Dimethoxynaphthalene With tin(IV) chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In water; dimethyl sulfoxide at 20℃; for 2h;	97%

2,7-Dimethoxynaphthalene (3469-26-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,7-dimethoxy-1-naphthalenecarbaldehyde (51385-93-4)

Conditions	Yield
With trichlorophosphate for 0.05h; Vilsmeier-Haack reaction; Microwave irradiation;	95%
With trichlorophosphate at 60℃;	95.3%
With trichlorophosphate at 60℃;	75.5%
With toluene; trichlorophosphate anschliessendes Erwaermen mit wss.Natriumacetat;
With trichlorophosphate In toluene	132 g

2,7-Dimethoxynaphthalene (3469-26-9) → 2,7-dimethoxy-1-naphthalenecarbaldehyde (51385-93-4)

Conditions	Yield
With dichloromethyl ether; titanium tetrachloride In dichloromethane at 0℃;	95.3%

2,7-Dimethoxynaphthalene (3469-26-9) → 1-bromo-2,7-dimethoxynaphthalene (4614-11-3)

Conditions	Yield
With bromine at 20℃;	91%
With aluminum tri-bromide; [bis(acetoxy)iodo]benzene In acetonitrile at 23℃;	84%
With N-Bromosuccinimide In dichloromethane at 20℃; for 18h;	81%
With chloroform; bromine
With bromine In chloroform

2,7-Dimethoxynaphthalene (3469-26-9) + para-methylphenylmagnesium bromide (4294-57-9) → 2,7-di(p-tolyl)naphthalene (1012085-52-7)

Conditions	Yield
With C68H72Cl2N6NiP2 In tetrahydrofuran at 25℃; for 24h; Inert atmosphere;	91%

Triisopropyl borate (5419-55-6) + 2,7-Dimethoxynaphthalene (3469-26-9) → C12H13BO4

Conditions	Yield
Stage #1: 2,7-Dimethoxynaphthalene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	88%

2,7-Dimethoxynaphthalene (3469-26-9) + 1,3-dimethyl-5-fluorouracil (3013-92-1) → (6aR,6bS,10aR,10bS)-6b-Fluoro-2,6a-dimethoxy-8,10-dimethyl-6a,10,10a,10b-tetrahydro-6bH-8,10-diaza-benzo[a]biphenylene-7,9-dione

Conditions	Yield
With penta-1,3-diene In acetonitrile UV-irradiation;	86%

2,7-Dimethoxynaphthalene (3469-26-9) + (2-methylphenyl)lithium (6699-93-0) → C24H20

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride In toluene at 20℃; for 12h; Schlenk technique; Inert atmosphere;	85%

2,7-Dimethoxynaphthalene (3469-26-9) → 1-Iodo-2,7-dimethoxynaphthalene

Conditions	Yield
With N-iodo-succinimide at 25℃; Inert atmosphere;	84%
With Iodine monochloride In acetonitrile	72.7%

2,7-Dimethoxynaphthalene (3469-26-9) + hexan-1-ol (111-27-3) → 2,7-bis(hexyloxy)naphthalene

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In water; 1,2-dichloro-ethane at 110℃; for 24h; Schlenk technique; Inert atmosphere;	84%

2,7-Dimethoxynaphthalene (3469-26-9) + N-methyl-N-phenylformamide (93-61-8) → 2,7-dimethoxy-1-naphthalenecarbaldehyde (51385-93-4)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane at 100℃; for 11h;	83%

Upstream product

• 146744-23-2 2-acetoxy-7-hydroxynaphthalene 
• 77-78-1 dimethyl sulfate 
• 765-43-5 Cyclopropyl methyl ketone 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 584-08-7 potassium carbonate 
• 74-83-9 methyl bromide 
• 1121-37-5 dicyclopropyl ketone 
• 872-75-3 1-(2,2-dimethyl-cyclopropyl)-ethanone 
• 108189-49-7 9,12-Dimethoxy-tricyclo[4.4.4.0^1,6]tetradeca-4,7,9,11,13-pentaen-3-one 
• 93750-00-6 Tricyclo[4.4.4.0^1,6]tetradeca-4,7,13-triene-3,9,12-trione 
• 71094-89-8 1-acetyl-2,6-dimethoxynaphthalene 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 25994-23-4 3,6-Dimethoxynaphthalic anhydride 

Downstream Products

• 51385-93-4 2,7-dimethoxy-1-naphthalenecarbaldehyde 
• 6223-34-3 3,6-dimethoxy-1,4-naphthoquinone 
• 83343-23-1 N-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine 
• 4003-89-8 2-amino-7-methoxy-1,2,3,4-tetrahydronaphthalene 
• 75965-66-1 2-hydroxy-7-methoxynaphthalene-1-carbaldehyde 
• 188427-83-0 C₄₀H₃₈N₆O₆ 
• 274911-52-3 benzyl 2-t-butyl-3-(3',6'-di-t-butyl-2',7'-dimethoxynaphthalene-1'-yl)-3-hydroxypropanoate 
• 274911-53-4 benzyl 2-t-butyl-3-(3',6'-di-t-butyl-2',7'-dimethoxynaphthalene-1'-yl)propanoate 
• 4785-56-2 2-formyl-5-methoxy-benzoic acid 
• 60373-42-4 2-formyl-4-methoxybenzoic acid 
• 188427-82-9 C₄₀H₃₄N₆O₁₀ 
• 188427-67-0 C₃₂H₂₈N₄O₅ 
• 71094-89-8 1-acetyl-2,6-dimethoxynaphthalene 
• 60683-71-8 1,4-dihydro-2,7-dimethoxynaphthalene 

Relevant academic research and scientific papers

A convenient strategy for the total synthesis of pisiferic acid type diterpenes

A practical method for the total synthesis of pisiferic acid type diterpenoids is described. This involves Robinson annulation of the keto ester for the key intermediate.

Facile access to a series of large polycondensed pyridazines and their utility for the supramolecular synthesis of coordination polymers

Domino cyclization of ketoenols and hydrazine leads to a series of polycondensed pyridazines, which reveal potential as rigid N-donor multidentate ligands for supramolecular synthesis of open coordination polymers.

Reduced Phenalenyl in Catalytic Dehalogenative Deuteration and Hydrodehalogenation of Aryl Halides

Dehalogenative deuteration reactions are generally performed through metal-mediated processes. This report demonstrates a mild protocol for hydrodehalogenation and dehalogenative deuteration of aryl/heteroaryl halides (39 examples) using a reduced odd alternant hydrocarbon phenalenyl under transition metal-free conditions and has been employed successfully for the incorporation of deuterium in various biologically active compounds. The combined approach of experimental and theoretical studies revealed a single electron transfer-based mechanism.

Enantiopure Chiral Concave 1,10-Phenanthrolines

Chiral information has been introduced into concave 1,10-phenanthrolines of different ring sizes by using a 2,7-disubstituted naphthalene bridgehead, which causes axial chirality. A tetraphenolic 2-(dihydroxynaphthyl)-9-(dihydroxyphenyl)-1,10-phenanthroline was synthesized as a key intermediate. Two strategies were followed to obtain the bimacrocyclic chiral concave 1,10-phenanthrolines: quadruple Williamson ether synthesis or alkenylation of the OH groups and subsequent ring-closing metathesis followed by hydrogenation. The overall yields of bimacrocyles 19 were 10 to 17 % starting from the respective Suzuki coupling of the substituted arenes 11 and 13 to 2,9-dichloro-1,10-phenanthroline (5). Racemic mixtures of the three concave 1,10-phenanthrolines 19 were separated by using chiral high-performance liquid chromatography (HPLC) techniques, and their absolute stereochemistry was assigned by comparison of simulated and experimental circular dichroism (CD) spectra. The enantiopure concave 1,10-phenanthrolines were used as ligands in a copper-catalysed cyclopropanation, and their selectivity was determined by chiral gas chromatography (GC).

1:1 and 2:1 cocrystallizations of alkoxy-substituted naphthalene derivatives with octafluoronaphthalene through arene-perfluoroarene interactions

Naphthalene derivatives with laterally orientated short side chains readily form cocrystals with octafluoronaphthalene in which the position and the length of the lateral chain can control the 1:1 and 2:1 cocrystallization stoichiometries and overlapped a

Synthesis and biological evaluation of 1-benzylidene-3,4-dihydronaphthalen- 2-one as a new class of microtubule-targeting agents

A series of 1-benzylidene-3,4-dihydronaphthalen-2-one derivatives were designed and synthesized, and their biological activities in vitro and in vivo were evaluated. The results showed a number of the title compounds exhibiting potent nanomolar activity in several human cancer cell lines. Of these, compound 22b showed the strongest inhibitory activity against human CEM, MDA-MBA-435, and K562 cells (IC50 = 1 nM), displayed in vitro inhibition of tubulin polymerization (IC50 = 3.93 μM), and significantly induced cell cycle arrest in G2/M phase. In addition, compound 22b could inhibit the tumor growth in colon nude mouse xenograft tumor model significantly and seemed safer than CA-4 when achieving a similar tumor suppression. This study provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

Synthesis and antifungal activities of novel 2-aminotetralin derivatives

Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoline ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14α-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

Tuning the size of macrocyclic cavities in trianglimine macrocycles

The synthesis of aromatic dicarboxaldehydes is described along with their reactivity in the [3 + 3] cyclocondensation reaction with (1R,2A)- diaminocyclohexane to give trianglimine macrocycles. In particular, the scope and limitation of the reaction with regard to complete control of the cavity size of the macrocycles is discussed producing a total of 11 macrocycles with different cavity sizes ranging from 9 to 23 A. The Royal Society of Chemistry 2005.

Photolytic, thermal, addition, and cycloaddition reactions of 2-diazo-5,6- and -3,8-disubstituted acenaphthenones

Preparation and varied thermal and photolytic reactions of 2-diazo-5,6-(disubstituted)acenaphthenones (11a-d) and 2-diazo-3,8- dimethoxyacenaphthenone (12) are reported. Alcohols react thermally and photolytically with 11a-c with losses of N2 to yield 2-alkoxynaphthenones (24a,b and 47a,b) and acenaphthenones (25 and 48a,b). Aniline and diphenylamine are converted by 11a-c at 180°C to acenaph[1,2-6]indoles (29a,b and 53a,b). Thermolyses of 11a-c at ～450°C (0.15 mmHg) yield reduction products 25 and 48a,b, respectively. Wolff rearrangements to 1,8-naphthyleneketenes (15a-d) and/or their derivatives are not observed in the above experiments. Oxygen converts 11a-c thermally to acenaphthenequinones (19a-c) and/or 1,8-naphthalic anhydrides. Insertion, addition, substitution, and/or isomerization reactions occur upon irradiation of 2-diazoacenaphthenones in cyclohexane, benzene, and tetrahydrofuran. Photolysis of 11d in benzene in the presence of O2 yields the insertion-oxidation product 2-hydroxy-5,6-dinitro-2-phenylacenaphthenone (60). Photolyses of 11a-c in nitriles result in N2 evolution and dipolar cycloaddition to give acenaph[1,2-d]oxazoles (41 and 61a,b). Acetylenes undergo thermal and photolytic cycloaddition/1,5-sigmatropic rearrangement reactions with 11a-d with N2 retention to give pyrazolo[5,1-a]quinolin-7-ones (69f-j). 2-Diazoacenaphthenones 1a and 11a react thermally and photolytically with electronegatively-substituted olefins with N2 expulsion to yield (E)- and (Z)-2-oxospiro[acenaphthylene-1(2H),1′cyclopropanes] 73a-c and 74a-c, respectively. The mechanisms of the reactions of la, 11a-d, and 12 reported are discussed.

Cyclopropylcarbinyl-type ring openings. Reconciling the chemistry of neutral radicals and radical anions

Cyclopropylcarbinyl → homoallyl and related rearrangements of radical ions (a) are frequently used as mechanistic "probes" to detect the occurrence of single electron transfer in chemical and biochemical processes, (b) provide the basis for mechanism-base