840-65-3

Basic information

• Product Name: DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE
• Synonyms: 2,6-Dicarbomethoxynaphthalene;Dimethyl ester of 2,6-naphthalenedicarboxylic acid;dimethyl2,6-naphthalate;NDC;DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE;DIMETHYL NAPHTHALENE-2,6-DICARBOXYLATE;2,6-NAPHTHALENEDICARBOXYLIC ACID DIMETHYL ESTER;2,6-NAPHTHALIC ACID DIMETHYL ESTER
• CAS NO: 840-65-3
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24
• EINECS: 212-661-4
• Product Categories: Naphthalene derivatives;C12 to C63;Carbonyl Compounds;Esters;Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 840-65-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 187-193 °C(lit.)
• Boiling Point: 347.16°C (rough estimate)
• Flash Point: 232°C
• Appearance: /
• Density: 1.2379 (rough estimate)
• Vapor Pressure: 7.88E-06mmHg at 25°C
• Refractive Index: 1.5389 (estimate)
• Storage Temp.: -196°C
• Water Solubility: Soluble in hot toluene (very faint turbidity). Insoluble in water.
• BRN: 987259
• CAS DataBase Reference: DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE(840-65-3)
• EPA Substance Registry System: DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE(840-65-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 840-65-3(Hazardous Substances Data)

Usage

Uses

Dimethyl naphthalene-2,6-dicarboxylate is used as a pharmaceutical intermediate.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C14H12O4/c1-17-13(15)11-5-3-10-8-12(14(16)18-2)6-4-9(10)7-11/h3-8H,1-2H3

Synthetic route

methanol (67-56-1) + 2,6-Naphthalenedicarboxylic acid (1141-38-4) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
With sulfuric acid for 24h; Reflux;	89%
With sulfuric acid Reflux;

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-methoxycarbonyl-6-naphthol p-toluenesulfonate → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
With sodium tetracarbonyl cobaltate; potassium carbonate; ethyl bromoacetate at 45℃; for 1.5h;	60%

methyl 2-(4-carbomethoxybenzylidene)-3-buten-1-oate (116503-70-9) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
5% Pd on active carbon In various solvent(s) for 5h;	55%
Pd on carbon In ethyl acetate; 1-Methylnaphthalene

methanol (67-56-1) + carbon monoxide (201230-82-2) + naphthalene-2,6-diyl bis(4-methylbenzenesulfonate) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
With sodium tetracarbonyl cobaltate; potassium carbonate; ethyl bromoacetate at 45℃; for 1.5h;	50%

diazomethane (186581-53-3, 908094-01-9) + 2,6-Naphthalenedicarboxylic acid (1141-38-4) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
With diethyl ether

methanol (67-56-1) + 2,6-dichloroformyl naphthalene (2351-36-2) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

dimethyl tricyclo<4.2.2.02,5>deca-3,7,9-triene-9,10-dicarboxylate (25733-20-4) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
(pyrolysis);

4-((Z)-3,3-Dimethoxy-2-methoxycarbonyl-but-1-enyl)-benzoic acid methyl ester (123207-12-5) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
at 475 - 500℃; vapor-phase pyrolysis; Yield given;

methanol (67-56-1) + 2,6-dichloroformyl naphthalene (2351-36-2) → naphthalene-2,6-dicarboxylic acid monomethyl ester (7568-08-3) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
With pyridine In dichloromethane

2,6-Naphthalenedicarboxylic acid (1141-38-4) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride, pyridine / CH2Cl2 2: pyridine / CH2Cl2 View Scheme

methanol (67-56-1) + polyethylene naphthalate + 2,6-Naphthalenedicarboxylic acid (1141-38-4) → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

Conditions	Yield
Product distribution / selectivity;

2,6-bis-(4-methyl-benzenesulfonyl)-naphthalene → dimethyl 2,6-naphthalenedicarboxylate (840-65-3)

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → 2,6-Naphthalenedicarboxylic acid (1141-38-4)

Conditions	Yield
Stage #1: dimethyl 2,6-naphthalenedicarboxylate With sodium hydroxide; water; butan-1-ol at 20 - 85℃; for 1h; Heating / reflux; Stage #2: With sulfuric acid In water Conversion of starting material;	100%
Stage #1: dimethyl 2,6-naphthalenedicarboxylate With polyethyleneglycol 4000; sodium hydroxide; water In xylene at 20 - 90℃; for 3.5h; Heating / reflux; Stage #2: With sulfuric acid In water Conversion of starting material;	99.5%
Stage #1: dimethyl 2,6-naphthalenedicarboxylate With sodium hydroxide; water; isopropyl alcohol at 80 - 81℃; for 2h; Stage #2: With sulfuric acid In water at 80℃; for 0.5h; Conversion of starting material;	99%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → naphthalene-2,6-dimethanol (5859-93-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 69.84℃; for 3h; Inert atmosphere; Cooling with ice;	97%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 24h;	93%
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere;	92%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → naphthalene-2,6-dicarboxylic acid monomethyl ester (7568-08-3)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; methanol at 80℃; for 2h;	96%
With lithium hydroxide In tetrahydrofuran for 26h; Heating / reflux;	94%
Stage #1: dimethyl 2,6-naphthalenedicarboxylate With potassium hydroxide In 1,4-dioxane; methanol at 80℃; for 4h; Stage #2: With hydrogenchloride In water pH=3;	82%

ethanolamine (141-43-5) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → C16H18N2O4

Conditions	Yield
at 120℃; for 3h; Inert atmosphere; Dean-Stark;	93.2%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → 2,6-naphthalene dicarbohydrazide (4073-74-9)

Conditions	Yield
With hydrazine hydrate In methanol; chloroform Heating;	87%
With hydrazine hydrate In methanol at 20℃; for 29h; Reflux;	83%
With hydrazine hydrate In methanol; water for 12h;	82%
With hydrazine hydrate In ethanol; chloroform for 4h; Reflux;	6.01 g

1-octadecanol (112-92-5) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → distearyl naphthalene-2,6-dicarboxylate

Conditions	Yield
Stage #1: 1-octadecanol; dimethyl 2,6-naphthalenedicarboxylate With Fascat 4100 In 5,5-dimethyl-1,3-cyclohexadiene at 160 - 180℃; for 20h; Inert atmosphere; Dean-Stark; Stage #2: In 5,5-dimethyl-1,3-cyclohexadiene at 180℃; under 1 - 2 Torr; for 0.166667h;	86%

4-phenyl-1-butylamine (13214-66-9) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → N,N'-Bis-(4-phenylbutyl)-naphthalene-2,6-dicarboxamide (141914-83-2)

Conditions	Yield
at 120℃; for 6h;	80%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → dimethyl 1 ,2,3,4-tetrahydronaphthalene-2,6-dicarboxylate (23985-75-3)

Conditions	Yield
With palladium on activated charcoal; hydrogen; acetic acid In isopropyl alcohol at 40℃; for 48h;	79%
With 5%-palladium/activated carbon; hydrogen In water; isopropyl alcohol at 100℃; under 7500.75 Torr; for 7h; Autoclave;	70%
With {RuCl(p-cymene)[(S,S)-(R,R)-phtrap]}Cl; hydrogen; caesium carbonate In 1,4-dioxane at 60℃; under 37503.8 Torr; for 24h;
With 5%-palladium/activated carbon; hydrogen; isopropyl alcohol at 170℃; under 7500.75 - 37503.8 Torr; for 1h; Time; Temperature; Pressure; Autoclave; Inert atmosphere;

trimethylsilyltributyltin (17955-46-3) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → methyl 6-(tributylstannyl)-2-naphthoate (1325730-39-9)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); potassium fluoride; 1,3-bis-(diphenylphosphino)propane; lithium chloride In toluene at 170℃; for 48h; Inert atmosphere; Glovebox;	74%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → methyl 6-hydroxymethyl-2-naphthalenecarboxylate (55343-77-6)

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0℃; for 0.5h;	65%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h;	31%
With methanol; sodium tetrahydroborate In tetrahydrofuran at 60℃; for 6h;
With diisobutylaluminium hydride In tetrahydrofuran at 0℃; for 0.5h;
With methanol; sodium tetrahydroborate In tetrahydrofuran at 60℃; for 6h;

aqueous sodium potassium (+)-tartrate + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → methyl 6-hydroxymethyl-2-naphthalenecarboxylate (55343-77-6)

Conditions	Yield
In toluene	65%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → O,O-dimethyl naphthalene-2,6-dicarbothioate (1243191-39-0) + methyl 6-methoxythiocarbonylnaphthalene-2-carboxylate (1243191-38-9)

Conditions	Yield
With Lawessons reagent In chlorobenzene for 6h; Reflux;	A 65% B 7%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → 2,6-naphthalenedicarbaldehyde (5060-65-1)

Conditions	Yield
Stage #1: dimethyl 2,6-naphthalenedicarboxylate With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Stage #2: With pyridinium chlorochromate In tetrahydrofuran; dichloromethane at 0℃; for 4h;	65%
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 69.84 °C / Inert atmosphere; Cooling with ice 2: pyridinium chlorochromate / dichloromethane / 4 h / 49.84 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 3.67 h / 19.99 - 69.84 °C / Inert atmosphere 2: pyridinium chlorochromate / dichloromethane / 4 h / 49.84 °C / Inert atmosphere View Scheme

4-(2-thiophenyl)morpholine (19983-19-8) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → C44H48N4O4S4*2ClHO4

Conditions	Yield
Stage #1: 4-(2-thiophenyl)morpholine With n-butyllithium In 1,4-dioxane; hexane at -15 - 0℃; Stage #2: dimethyl 2,6-naphthalenedicarboxylate With perchloric acid In 1,4-dioxane; hexane for 8h; Heating;	61%

acetonitrile (75-05-8) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → methyl 6-(2-cyanoacetyl)-2-naphthalenecarboxylate

Conditions	Yield
Stage #1: acetonitrile; dimethyl 2,6-naphthalenedicarboxylate With sodium t-butanolate at 60℃; for 1.5h; Stage #2: With sulfuric acid In water at 25℃; for 1h;	60%

allyl-trimethyl-silane (762-72-1) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → dimethyl (2RS,2aSR,3SR,4SR,8bRS)-1,2,2a,3,4,8b-hexahydro-2,4-methanocyclobutanaphthalene-3,7-dicarboxylate

Conditions	Yield
In methanol; acetonitrile Ambient temperature; Irradiation;	55%

2-(prop-2-ynyloxy)ethanol (3973-18-0) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → bis[2-(prop-2-yn-1-yloxy)ethyl] naphthalene-2,6-dicarboxylate

Conditions	Yield
Stage #1: 2-(prop-2-ynyloxy)ethanol With sodium hydride In tetrahydrofuran; mineral oil Schlenk technique; Inert atmosphere; Stage #2: dimethyl 2,6-naphthalenedicarboxylate In tetrahydrofuran; mineral oil at 130℃; for 0.75h; Schlenk technique; Inert atmosphere;	42%

acetone (67-64-1) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → 1,1'-(2,6-naphthylene)bisbutane-1,3-dione

Conditions	Yield
With sodium amide In diethyl ether at -0.16 - 24.84℃; for 4h; Claisen condensation;	37%

dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → naphthalene-2,6-dimethanol (5859-93-8) + methyl 6-hydroxymethyl-2-naphthalenecarboxylate (55343-77-6)

Conditions	Yield
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 4.5h;	A 31% B 18%

ethanol (64-17-5) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → diethyl naphthalene-2,6-dicarboxylate (15442-73-6)

Conditions	Yield
With potassium cyanide	25%

2-(2-(prop-2-ynyloxy)ethoxy)ethanol (7218-43-1) + dimethyl 2,6-naphthalenedicarboxylate (840-65-3) → bis{2-[2-(prop-2-yn-1-yloxy)ethoxy]ethyl} naphthalene-2,6-dicarboxylate

Conditions	Yield
Stage #1: 2-(2-(prop-2-ynyloxy)ethoxy)ethanol With sodium hydride In tetrahydrofuran; mineral oil Schlenk technique; Inert atmosphere; Stage #2: dimethyl 2,6-naphthalenedicarboxylate In tetrahydrofuran; mineral oil at 130℃; for 0.75h; Schlenk technique; Inert atmosphere;	14%

Upstream product

• 186581-53-3 diazomethane 
• 1141-38-4 2,6-Naphthalenedicarboxylic acid 
• 91-57-6 2-Methylnaphthalene 
• 69750-34-1 2-methyl-6-propanoyl naphthalene 
• 5156-83-2 6-methyl-2-acetonaphthone 
• 67-56-1 methanol 
• 2351-36-2 2,6-dichloroformyl naphthalene 
• 116503-70-9 methyl 2-(4-carbomethoxybenzylidene)-3-buten-1-oate 
• 123207-12-5 4-((Z)-3,3-Dimethoxy-2-methoxycarbonyl-but-1-enyl)-benzoic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 25733-20-4 dimethyl tricyclo<4.2.2.0^2,5>deca-3,7,9-triene-9,10-dicarboxylate 

Downstream Products

• 141914-83-2 N,N'-Bis-(4-phenylbutyl)-naphthalene-2,6-dicarboxamide 
• 5859-93-8 naphthalene-2,6-dimethanol 
• 5159-60-4 6-cyano-naphthalene-2-carboxylic acid 
• 71590-35-7 2-Cyan-6-benzoylaminonaphthalen 
• 71590-41-5 2-Thiocarboxamido-6-benzoylaminonaphthalen 
• 5088-91-5 6-cyano-naphthalene-2-carboxylic acid methyl ester 
• 129667-70-5 6-amino-2-naphthalenecarbonitrile 
• 71590-43-7 2-Methylmercaptoiminocarbonyl-6-benzoylaminonaphthalen-hydroiodid 
• 653604-26-3 6-(N-phenyl-N-methylcarbamyl)-2-naphthalenecarbonitrile 
• 653604-31-0 6-(1-oxo-2-phenylethyl)-2-naphthalenecarbonitrile 
• 653604-40-1 6-[N-(3-methoxyphenyl)carbamyl]-2-naphthalenecarbonitrile 
• 653604-35-4 6-[N-(4-ethylphenyl)carbamyl]-2-naphthalenecarbonitrile 
• 653604-34-3 6-[N-(4-(hydroxymethyl)phenyl)carbamyl]-2-naphthalenecarbonitrile 
• 653604-41-2 6-[N-(3-ethoxyphenyl)carbamyl]-2-naphthalenecarbonitrile 

Relevant articles and documents

Preparation method of dimethyl 2, 6-naphthalate

The invention discloses a preparation method of dimethyl 2, 6-naphthalate. Specifically, the preparation method of the dimethyl 2, 6-naphthalate disclosed by the invention comprises the following steps: carrying out esterification reaction on 2, 6-naphthalic acid and methanol under a pressurization condition in the presence of a catalyst, and filtering without further purification to obtain the dimethyl 2, 6-naphthalate, wherein the mass ratio of the methanol to the 2, 6-naphthalic acid is (3: 1)-(25: 1), the reaction temperature ranges from 100 DEG C to 150 DEG C. According to the preparation method disclosed by the invention, the operation is simplified, the yield of the dimethyl 2, 6-naphthalate is improved, and meanwhile, the purity of the dimethyl 2, 6-naphthalate is maintained.

Primary coloured electrochromism of aromatic oxygen and sulfur diesters

Eleven aromatic diesters and thioic S,S′-diesters were synthesized and investigated using electrochemical (cyclic voltammetry and controlled potential electrolysis) and UV-vis spectroscopic techniques over a range of temperatures. Nine of the compounds exhibited vibrant colour changes from a colourless state in their neutral forms to brightly coloured upon one-electron electrochemical reduction in acetonitrile. The compounds were found to display either red, green or blue colours in their one-electron reduced states. The electrochromic properties of 3 of the compounds that displayed the most vibrant colour changes were examined in solution using a gold micro-mesh electrode laminated inside a polymer film.

Catalyst for carbonylating naphthalene mono- and disulfonates and process using said catalyst

A cobalt based catalyst, and the method for preparing it, are disclosed. The catalyst is obtained from the reaction between NaCo(CO)4 and s-trichloro triazine and is advantageously used in the processes of carbonylation of naphthalene mono- and disulfonates in order to yield naphthalene esters and acids.