DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE

DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE Property

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)

Safety

Safety Statements 

22-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

2917.39.7000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H372Causes damage to organs through prolonged or repeated exposure

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P314Get medical advice/attention if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

DIMETHYL 2,6-NAPHTHALENEDICARBOXYLATE Chemical Properties,Usage,Production

Uses

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

Flammability and Explosibility

Non flammable

Synthesis

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