2,3-Naphthalenedicarboxylic Anhydride Chemical Properties

Melting point:

246 °C

Boiling point:

275-280 °C(Press: 100 Torr)

Density 

1.449±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

color 

Pale Beige

Stability:

Moisture Sensitive

InChI

InChI=1S/C12H6O3/c13-11-9-5-7-3-1-2-4-8(7)6-10(9)12(14)15-11/h1-6H

InChIKey

IZJDCINIYIMFGX-UHFFFAOYSA-N

SMILES

O1C(=O)C2=CC3C(C=C2C1=O)=CC=CC=3

EPA Substance Registry System

Naphtho[2,3-c]furan-1,3-dione (716-39-2)

Safety Information

Safety Statements 

22-24/25

HS Code 

2917.39.7000

2,3-Naphthalenedicarboxylic Anhydride Usage And Synthesis

Appearance

2,3-NAPHTHALENEDICARBOXYLIC ANHYDRIDE is a pale Beige Solid.

Description

A few years ago, the product was still synthesized from the corresponding diacid, but in recent years, it has been difficult to find the shadow of the diacid in the market, and the sales of this product have been repeatedly restricted, resulting in high prices.

Uses

2,3-Naphthalic anhydride is used as a reagent to synthesize analogues of Thalidomide (T338850), an inhibitor of tumour necrosis factor that was once abandoned because it caused birth defects, but is currently used as an inhibitor of angiogenesis in patients with multiple myeloma.

Preparation

Add anhydrous tetrahydrofuran (its mass ratio to maleic anhydride is 1.5:1), cat-1 (0.05 mole), maleic anhydride (1 mole), and o-phthalaldehyde (1.5 mole) to the reactor. After adding triethylamine (5 moles), adjust the temperature below -40°C. Silicon tetrachloride (4 moles) was added dropwise to the reaction system and the reaction was placed at -40 °C for 4 h. The mixture was heated to reflux for 20 h. After the end of the reaction, concentrating the solution to a certain concentration with diatomaceous earth filtration. A light yellow solid, namely 2,3-Naphthalenedicarboxylic Anhydride, is obtained by precipitation, filtration, recrystallization and drying. Its yield reaches 88%.

2,3-Naphthalenedicarboxylic Anhydride(716-39-2)Related Product Information

• 2,3-Naphthalenedicarboxylic Anhydride
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• 4-Amino-1,8-naphthalenedicarboxylic anhydride
• 4-Nitro-1,8-naphthalenedicarboxylic anhydride
• 1-PHENYL-2 3-NAPHTHALENEDICARBOXYLIC
• 1,2-NAPHTHALENEDICARBOXYLIC ANHYDRIDE
• 1-PHENYL-2,3-NAPHTHALENEDICARBOXYLIC ANHYDRIDE
• AKOS 92363