23204-36-6

Basic information

• Product Name: 3-HYDROXY-1,8-NAPHTHALIC ANHYDRIDE
• Synonyms: hydroxynaphthalicanhydride;3-HYDROXY-1,8-NAPHTHALIC ANHYDRIDE;5-HYDROXY-BENZO[DE]ISOCHROMENE-1,3-DIONE;3-Hydroxy-1,8-naphthalenedicarboxylic anhydride;5-hydroxy-1H,3H-benzo[de]isochromene-1,3-dione;3-Hydroxy-1,8-naphthalenedicarboxylic acid=anhydride ester;3-Hydroxynaphthalene-1,8-dicarboxylic anhydride;Albb-005281
• CAS NO: 23204-36-6
• Molecular Formula: C₁₂H₆O₄
• Molecular Weight: 214.17
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 23204-36-6.mol

Chemical Properties

• Melting Point: 281 °C
• Boiling Point: 509.4 °C at 760 mmHg
• Flash Point: 210.8 °C
• Appearance: /
• Density: 1.585 g/cm³
• Vapor Pressure: 5.36E-11mmHg at 25°C
• Refractive Index: 1.756
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Dimethylformamide
• PKA: 7.93±0.20(Predicted)
• CAS DataBase Reference: 3-HYDROXY-1,8-NAPHTHALIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-1,8-NAPHTHALIC ANHYDRIDE(23204-36-6)
• EPA Substance Registry System: 3-HYDROXY-1,8-NAPHTHALIC ANHYDRIDE(23204-36-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 23204-36-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H6O4/c13-7-4-6-2-1-3-8-10(6)9(5-7)12(15)16-11(8)14/h1-5,13H

Upstream product

• 4053-08-1 p-chloro-1,8-naphthalicanhydride 
• 23204-38-8 3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 
• 3027-38-1 3-nitro-1,8-naphthalic anhydride 
• 81-84-5 1,8-Naphthalic anhydride 
• 174530-06-4 3-sulfo-naphthalene-1,8-dicarboxylic acid 
• 69409-07-0 1,3-dioxo-1H,3H-naphtho<1,8-cd>pyran-5-sulfonic acid 

Downstream Products

• 59841-55-3 5-hydroxy-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 23204-41-3 5-hydroxy-benz[de]isoquinoline-1,3-dione 

Relevant articles and documents

Design, synthesis, and evaluation of novel 3-carboranyl-1,8-naphthalimide derivatives as potential anticancer agents

We synthesized a series of novel 3-carboranyl-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, using click chemistry, reductive amination and amidation reactions and investigated their in vitro effects on cytotoxicity, cell death, cell cycle, and the production of reactive oxygen species in a HepG2 cancer cell line. The analyses showed that modified naphthalic anhydrides and naphthalimides bearing ortho-or meta-carboranes exhibited diversified activity. Naphthalimides were more cytotoxic than naphthalic anhydrides, with the highest IC50 value determined for compound 9 (3.10 μM). These compounds were capable of inducing cell cycle arrest at G0/G1 or G2M phase and promoting apoptosis, autophagy or ferroptosis. The most promising conjugate 35 caused strong apoptosis and induced ROS production, which was proven by the increased level of 2′-deoxy-8-oxoguanosine in DNA. The tested conjugates were found to be weak topoisomerase II inhibitors and classical DNA intercalators. Compounds 33, 34, and 36 fluorescently stained lysosomes in HepG2 cells. Additionally, we performed a similarity-based assessment of the property profile of the conjugates using the principal component analysis. The creation of an inhibitory profile and descriptor-based plane allowed forming a structure–activity landscape. Finally, a ligand-based comparative molecular field analysis was carried out to specify the (un)favorable structural modifications (pharmacophoric pattern) that are potentially important for the quantitative structure– activity relationship modeling of the carborane–naphthalimide conjugates.

PERI-XANTHENOXANTHENE BISIMIDE COMPOUND, METHOD FOR PRODUCING THE SAME, ORGANIC EL ELEMENT, AND ORGANIC THIN FILM SOLAR CELL

PROBLEM TO BE SOLVED: To provide a novel compound that can be used as an n-type semiconductor material in an organic semiconductor product such as an organic EL element and an organic thin film solar cell. SOLUTION: The present invention provides a peri-xanthenoxanthene bisimide compound represented by the formula (R is an alkyl group, a substitutable aryl group or the like; Xa1, Xa2, Y1, Y2, Z1 and Z2 independently represent H, halogen, a substitutable aryl group, an aromatic heterocyclic group or the like). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Isomeric naphthalimides bearing pyran units: Insight into mutual relation between structure and photochromic properties

Two novel isomeric photochromic naphthopyrans (1 and 2) containing naphthalimide moieties were prepared and studied. In the compound 1, O-atom of pyran cycle is at C-3 position of naphthalene ring, whereas, in compound 2, O-atom of pyran cycle is at C-4 position. In the compound 2 due to para-position O-atom of pyran photochrome cycle is involved into the conjugated naphthalimide system. The variety in mutual position of pyran and naphthalimide units leads to remarkable difference in photochromic characteristics. Both compounds demonstrate the switching of the fluorescence by photoinduced conversion between the closed and open forms.

Detection of the 1,2-Didehydronaphthalene to 1H-Indenylidenecarbene Rearrangement by Intramolecular Trapping in a Flash Vacuum Pyrolytic Reaction

Flash vacuum pyrolysis of 9-methyl-1,3-dihydronaphthofuran-1,3-dione (8) at 750-880 deg gave exclusively 1H-cyclopentindene (9) and of 8-methyl-1,2-dihydrocyclobutanaphthalene-1.2-dione (10) at 600-840 deg gave a mixture of (9) and acenaphthylene.Acenaphthylen-4-ol (12) was synthesized and found to be stable to flash vacuum pyrolysis over the temperature range 600-900 deg.These findings are discussed in relation to the rearrangement described in the title.

Novel ortho-quinone diazide photoresist sensitizers

Ortho-quinone diazide compounds of the formula STR1 wherein R is an organic radical are useful sensitizers for photoresist compositions and intermediates for novel dyes.