Naphtho(2,3-c)furan-1,3-dione
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Basic information
- CAS
716-39-2- Standard SMILES
O=C1OC(=O)c2cc3ccccc3cc21- InChIKey
IZJDCINIYIMFGX-UHFFFAOYSA-N- Molecular formula
- C12H6O3
- Average molar mass
- 198.17 g/mol
- Monoisotopic mass
- 198.03169405
Names & identifiers
- Preferred name
- Naphtho(2,3-c)furan-1,3-dione
- IUPAC
- benzo[f][2]benzofuran-1,3-dione
- English name
- 2,3-Naphthalenedicarboxylic Anhydride
- Molecular formula
- C12H6O3
- Molecular weight
- 198.17
Names & synonyms
naphtho[2,3-c]furan-1,3-dione716-39-22,3-Naphthalenedicarboxylic AnhydrideEINECS 211-936-6Naphtho(2,3-c)furan-1,3-dioneDTXSID9061049RefChem:832032DTXCID6047078211-936-62,3-naphthalic anhydrideMFCD00059091benzo[f][2]benzofuran-1,3-dione
Show more names
EA2532,3-NAPHTHALI2,3-Napthalenedicarboxycanhydridebenzo[f]isobenzofuran-1,3-quinone2,3-NaphthalenedicarboxylicAnhydride>1,3-Dihydronaphtho[2,3-c]furan-1,3-dione
naphthalene-2,3-dicarboxylic anhydridebenzo[f]isobenzofuran-1,3-dione1H,3H-naphtho[2,3-c]furan-1,3-dioneAYA8A7JT6PSCHEMBL103SCHEMBL30083328AAA716392,3-napthalenedicarboxylic anhydride
Database identifiers
- CAS
716-39-2- PubChem CID
- 69743
- DTXSID
DTXSID9061049- UNII
- AYA8A7JT6P
- EC Number
- 211-936-6
- Nikkaji
- J193.086I
Properties
Computed structural propertiesFilling in
- XLogP
- 2.5
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 280
Physicochemical properties
- Melting point
- 246 °C · 246 °C
- Boiling point
- 275 · 275-280 °C(Press: 100 Torr)
- Density
- 1.449 · 1.449±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 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
- 2 · Naphtho[2,3-c]furan-1,3-dione (716-39-2)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- tsca
- TSCA listed
- hs_code
- 2917.39.7000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationNaphtho[2,3-c]furan-1,3-dione: INACTIVE
Applications
DescriptionA 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.
Uses2,3-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 methods
PreparationAdd 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%.
Upstream & downstream products
Upstream raw materials
Related reactions
15 records
Compound notes
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