2,3-Naphthalenedicarboxylic Anhydride

2,3-Naphthalenedicarboxylic Anhydride Property

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

Safety Statements 

22-24/25

HS Code 

2917.39.7000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,3-Naphthalenedicarboxylic Anhydride Chemical Properties,Usage,Production

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%.

Synthesis

In a 5 mL sealed tube, tert-butyl peroxybenzoate (TBPB, 30 mol%, 0.041 g) and 70 wt% aqueous tert-butyl hydroperoxide (TBHP, 1.0 mmol, 0.131 g) were added to a solution of benzyl alcohol 1a (0.4 mmol, 0.043 g) dissolved in chlorobenzene (1 mL). The reaction mixture was heated at 80°C for 2.5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the mixture was cooled to room temperature and saturated sodium bicarbonate solution (2 mL) was added. The reaction product was extracted with ethyl acetate (2 x 3 mL). The organic phases were combined and dried with anhydrous sodium sulfate (Na2SO4). The solvent was removed by concentration under reduced pressure. The residue was purified by column chromatography using hexane-ethyl acetate (15:1, v/v) as eluent to afford pure 2,3-naphthalenedicarboxylic anhydride (2a) as a white solid.

References

[1] Synlett, 2018, vol. 29, # 1, p. 136 - 140