2,3-Naphthalenedicarboxylic Anhydride
- CAS NO.:716-39-2
- Empirical Formula: C12H6O3
- Molecular Weight: 198.17
- MDL number: MFCD00059091
- EINECS: 211-936-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 14:15:32
What is 2,3-Naphthalenedicarboxylic Anhydride?
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.
The Uses of 2,3-Naphthalenedicarboxylic Anhydride
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%.
Properties of 2,3-Naphthalenedicarboxylic Anhydride
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 |
EPA Substance Registry System | Naphtho[2,3-c]furan-1,3-dione (716-39-2) |
Safety information for 2,3-Naphthalenedicarboxylic Anhydride
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2,3-Naphthalenedicarboxylic Anhydride
InChIKey | IZJDCINIYIMFGX-UHFFFAOYSA-N |
SMILES | O1C(=O)C2=CC3C(C=C2C1=O)=CC=CC=3 |
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