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DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE

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DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE Basic information

Product Name:
DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE
Synonyms:
  • 2,6-Dicarbomethoxynaphthalene
  • Dimethyl ester of 2,6-naphthalenedicarboxylic acid
  • dimethyl2,6-naphthalate
  • 2,6-Naphthalenedicarboxylic acid, 2,6-dimethyl ester
  • NDC
  • DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE
  • DIMETHYL NAPHTHALENE-2,6-DICARBOXYLATE
  • 2,6-NAPHTHALENEDICARBOXYLIC ACID DIMETHYL ESTER
CAS:
840-65-3
MF:
C14H12O4
MW:
244.24
EINECS:
212-661-4
Product Categories:
  • Building Blocks
  • C12 to C63
  • Carbonyl Compounds
  • Chemical Synthesis
  • Organic Building Blocks
  • Naphthalene derivatives
  • C12 to C63
  • Carbonyl Compounds
  • Esters
Mol File:
840-65-3.mol
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DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE Chemical Properties

Melting point:
187-193 °C(lit.)
Boiling point:
347.16°C (rough estimate)
Density 
1.2379 (rough estimate)
vapor pressure 
0Pa at 25℃
refractive index 
1.5389 (estimate)
Flash point:
232°C
storage temp. 
Sealed in dry,Room Temperature
form 
powder to crystal
color 
White to Almost white
Water Solubility 
Soluble in hot toluene (very faint turbidity). Insoluble in water.
BRN 
987259
InChI
InChI=1S/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
InChIKey
GYUVMLBYMPKZAZ-UHFFFAOYSA-N
SMILES
C1=C2C(C=C(C(OC)=O)C=C2)=CC=C1C(OC)=O
LogP
3.5 at 25℃
CAS DataBase Reference
840-65-3(CAS DataBase Reference)
EPA Substance Registry System
Dimethyl 2,6-naphthalenedicarboxylate (840-65-3)
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Safety Information

Safety Statements 
22-24/25
WGK Germany 
3
TSCA 
Yes
HS Code 
2917.39.7000

MSDS

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DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE Usage And Synthesis

Uses

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

Flammability and Explosibility

Non flammable

Synthesis

67-56-1

1141-38-4

840-65-3

To a round bottom flask was added 20 g of 2,6-naphthalenedicarboxylic acid dissolved in 150 mL of methanol and 15 mL of concentrated sulfuric acid was added as a catalyst. The reaction mixture was heated to reflux for 24 hours to complete the esterification reaction. Upon completion of the reaction, the mixture was slowly poured into 500 mL of ice water to quench the reaction. The resulting white precipitate was collected by diafiltration and washed with plenty of water to remove residual acid and methanol. Finally, the product was dried in a vacuum drying oven to give 20 g of dimethyl 2,6-naphthalenedicarboxylate in 89% yield.

References

[1] Patent: CN103864711, 2016, B. Location in patent: Paragraph 0102; 0103; 0104
[2] RSC Advances, 2014, vol. 4, # 35, p. 18100 - 18107

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