3469-26-9

Basic information

• Product Name: 2,7-Dimethoxynaphthalene
• Synonyms: 2,7-DIMETHOXYNAPHTHALENE;2,7-DimethoxylNaphthalene;2,7-Dimethoxy;2,7-DIMETHOXYNAPHTHALENE, 99% PHARM GRADE;Naphthalene, 2,7-dimethoxy-;2,7-Dimethoxynaphthalene,98%;2,7- twoMethoxy naphthalene
• CAS NO: 3469-26-9
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.22
• EINECS: 222-433-6
• Product Categories: FINE Chemical & INTERMEDIATES;Naphthalene derivatives;API intermediates;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 3469-26-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 283.23°C (rough estimate)
• Flash Point: 130.3 °C
• Appearance: off-white to brown crystalline powder
• Density: 1.0750 (rough estimate)
• Vapor Pressure: 0.00105mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,7-Dimethoxynaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dimethoxynaphthalene(3469-26-9)
• EPA Substance Registry System: 2,7-Dimethoxynaphthalene(3469-26-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3469-26-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white to brown crystalline powder

Uses

2,7-Dimethoxynaphthalene was employed as matrix to investigate the structure of polymetallic porphyrins via matrix-assisted laser desorption/ionization. It was also used in the synthesis of:peri-aroylnaphthalene compounds via elective electrophilic aromatic aroylation2-amino-1,2,3,4-tetrahydronaphthalene-6,7-diol

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

• 1121-37-5 dicyclopropyl ketone 
• 582-17-2 2,7-Dihydroxynaphthalene 
• 584-08-7 potassium carbonate 
• 74-83-9 methyl bromide 
• 872-75-3 1-(2,2-dimethyl-cyclopropyl)-ethanone 
• 765-43-5 Cyclopropyl methyl ketone 
• 146744-23-2 2-acetoxy-7-hydroxynaphthalene 
• 77-78-1 dimethyl sulfate 
• 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

• 4133-34-0 7-methoxyl-2-tetralone 
• 6223-34-3 3,6-dimethoxy-1,4-naphthoquinone 
• 4614-12-4 dibromo-1,6 dimethoxy-2,7 naphtalene 
• 4785-56-2 2-formyl-5-methoxy-benzoic acid 
• 60373-42-4 2-formyl-4-methoxybenzoic acid 
• 60683-71-8 1,4-dihydro-2,7-dimethoxynaphthalene 
• 51385-93-4 2,7-dimethoxy-1-naphthalenecarbaldehyde 
• 86358-80-7 1,8-dibenzoyl-2,7-dimethoxynaphthalene 
• 86358-79-4 2-benzoyl-3,6-dimethoxynaphthalene 
• 86358-78-3 1-benzoyl-2,7-dimethoxynaphthalene 
• 274911-53-4 benzyl 2-t-butyl-3-(3',6'-di-t-butyl-2',7'-dimethoxynaphthalene-1'-yl)propanoate 
• 274911-52-3 benzyl 2-t-butyl-3-(3',6'-di-t-butyl-2',7'-dimethoxynaphthalene-1'-yl)-3-hydroxypropanoate 
• 1092964-03-8 1-acetyl-1-hydroxy-8-methoxy-3-(2'-methoxyphenyl)-1H-benzo[e]indol-2(3H)-one 
• 1092963-80-8 2-acetoxy-2-(2,7-dimethoxy-1-naphthyl)-N-(2'-methoxyphenyl)-3-oxobutanamide 

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