81-83-4

Basic information

• Product Name: 1,8-Naphthalimide
• Synonyms: 2H-Benzo[de]isoquinoline-1,3-dione;Naphthalene-1,8-dicarbimide;Naphthalic acid imide;1,8-Naphthalimide,94%;1,8-NaphthaliMide 99%;NAPHTHALIMIDE;1h-benz[de]isoquinoline-1,3(2h)-dione;1,8-NAPHTHALIMIDE
• CAS NO: 81-83-4
• Molecular Formula: C₁₂H₇NO₂
• Molecular Weight: 197.19
• EINECS: 201-379-7
• Product Categories: Cyclic Imides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Intermediates of Dyes and Pigments;organic intermediate;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 81-83-4.mol

Chemical Properties

• Melting Point: 299-300 °C(lit.)
• Boiling Point: 334.29°C (rough estimate)
• Flash Point: 208.9 °C
• Appearance: off-white to white powder
• Density: 1.2292 (rough estimate)
• Vapor Pressure: 2.41E-13mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.48±0.20(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 153150
• CAS DataBase Reference: 1,8-Naphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Naphthalimide(81-83-4)
• EPA Substance Registry System: 1,8-Naphthalimide(81-83-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36
• Safety Statements: 37/39-26
• WGK Germany: 1
• TSCA: Yes
• Hazardous Substances Data: 81-83-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Light Emitting Diodes (OLEDs) Industry:
1,8-Naphthalimide is used as a phosphorescence dye in OLEDs for its ability to emit light upon excitation. This property makes it a valuable component in the development of efficient and long-lasting OLEDs.
Used as Hole Blocking Material:
1,8-Naphthalimide serves as a hole blocking material in electronic devices, preventing the recombination of electrons and holes, which can improve the overall performance and efficiency of the device.
Used as Electron-conducting Material:
Due to its electron-conducting properties, 1,8-Naphthalimide is utilized in the development of electronic materials and devices, such as sensors and transistors, where efficient electron transport is crucial for their operation.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C12H10N2O2/c13-11(15)8-5-1-3-7-4-2-6-9(10(7)8)12(14)16/h1-6H,(H2,13,15)(H2,14,16)

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 33489-49-5 acenaphthenequinone monoxime 
• 518-05-8 Naphthalene-1,8-dicarboxylic acid 
• 5811-88-1 8-carbamoyl-[1]naphthoic acid 
• 94374-88-6 2-benzylideneamino-benzo[de]isoquinoline-1,3-dione 
• 408329-24-8 N-(2-acetyloxyethyl)-1,8-naphthalimide 
• 1875-48-5 N-aminophthalamide 
• 79-37-8 oxalyl dichloride 
• 91-20-3 naphthalene 
• 1118-02-1 trimethylsilyl isocyanate 
• 253875-98-8 dimethylaminopropionitrile hydrobromide 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 1738-25-6 3-dimethylaminopropiononitrile 
• 94194-33-9 N-(2-phenylallyl)naphthalene-1,8-dicarboximide 

Downstream Products

• 5450-40-8 2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 130-00-7 1,8-naphtholactam 
• 22817-26-1 2,3-dihydro-1H-benzo[de]isoquinoline 
• 81-33-4 3,4,9,10-perylene tetracarboxyxlic acid diimide 
• 131140-40-4 2-{2-[(1R,2S,3R)-3-Benzyl-2-((Z)-propenyl)-cyclopentyl]-allyl}-benzo[de]isoquinoline-1,3-dione 
• 2896-24-4 N-benzyl-1,8-naphthalimide 
• 280-57-9 1,4-diazabicyclo[2.2.2]octane radical cation 
• 91-20-3 naphthalene 
• 1875-48-5 N-aminophthalamide 
• 625123-60-6 2-(3-{4-[(2S,4R)-2-(Bis-ethylsulfanyl-methyl)-4-hydroxy-pyrrolidine-1-carbonyl]-2-methoxy-5-nitro-phenoxy}-propyl)-benzo[de]isoquinoline-1,3-dione 
• 6914-98-3 2-phenylbenzo[de]isoquinoline-1,3-dione 

Relevant articles and documents

Independent Generation and Reactivity of 2′-Deoxyguanosin- N1-yl Radical

2′-Deoxyguanosin-N1-yl radical (dG(N1-H)?) is the thermodynamically favored one-electron oxidation product of 2′-deoxyguanosine (dG), the most readily oxidized native nucleoside. dG(N1-H)? is produced by the formal dehydration of a hydroxyl radical adduct of dG as well as by deprotonation of the corresponding radical cation. dG(N1-H)? were formed as a result of the indirect and direct effects of ionizing radiation, among other DNA damaging agents. dG(N1-H)? was generated photochemically (λmax = 350 nm) from an N-aryloxy-naphthalimide precursor (3). The quantum yield for photochemical conversion of 3 is ～0.03 and decreases significantly in the presence O2, suggesting that bond scission occurs from a triplet excited state. dG is formed quantitatively in the presence of excess β-mercaptoethanol. In the absence of a reducing agent, dG(N1-H)? oxidizes 3, decreasing the dG yield to ～50%. Addition of 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodGuo) as a sacrificial reductant results in a quantitative yield of dG and two-electron oxidation products of 8-oxodGuo. N-Aryloxy-naphthalimide 3 is an efficient and high-yielding photochemical precursor of dG(N1-H)? that will facilitate mechanistic studies on the reactivity of this important reactive intermediate involved in DNA damage.

Synthesis and fluorescence study of naphthalimide-coumarin, naphthalimide-luminol conjugates

Fluorescent naphthalimide-coumarin and naphthalimide-luminol conjugates were prepared by nucleophilic substitution reaction. The synthesized conjugates were characterized by 1H-NMR, 13C-NMR, mass and IR spectra. The absorption and fluorescence of these conjugates revealed that naphthalimide-luminol conjugates are more fluorescent than the naphthalimide-coumarin conjugates. In proton accepting DMSO solvent the fluorescence of the conjugates was quenched, while in proton donating ethanol solvent enhanced fluorescence was noticed. Based on the excitation maxima and fluorescence maxima it was found that in naphthalimide-coumarin conjugates coumarin acting as donor and naphthalimide acting as acceptor where as in naphthalimide-luminol conjugates naphthalimide acts as donor and luminol acts as acceptor.

Novel chiral naphthalimide-cycloalkanediamine conjugates: Design, synthesis and antitumor activity

A novel series of enantiopure naphthalimide-cycloalkanediamine conjugates were designed, synthetized and evaluated for in vitro cytotoxicity against human colon adenocarcinoma (LoVo), human lung adenocarcinoma (A549), human cervical carcinoma (Hela) and human promyelocytic leukemia cell lines (HL-60). The cytotoxicity of the compounds was highly dependent on size and relative stereochemistry of the cycloalkyl ring as well as length of the spacer. By contrast, any kind of enantioselection was observed for each pair of enantiomers. Flow cytometric analysis indicated that compounds 22 and 23 could effectively induce G2/M arrest in the four previous cell lines despite a mild apoptotic effect.

Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea

N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.

Cytotoxicity, anticancer, and antioxidant properties of mono and bis-naphthalimido β-lactam conjugates

This article reports the diastereoselective synthesis of some novel naphthalimido and bis-naphthalimido β-lactam derivatives and a preliminary evaluation of their anticancer properties. The reactions were completely diastereoselective, leading exclusively to the formation of cis-β-lactams 11a–l and trans-bis-β-lactams 16a–g. All of these compounds were obtained in good to excellent yields and their structures were established based on IR, 1H NMR, 13C NMR spectral data, and elemental analysis. Each of the β-lactams was screened for antioxidant and anticancer activities. Our results showed that all the compounds lacked cytotoxicity against HepG2 cells, whereas 16a and 16b exhibited excellent anticancer activity with IC50 values below 191.57 μM on MCF-7 cell line and also, bis-β-lactams 16a–g showed excellent antitumor activity against the TC-1 cell line. Antioxidant experiments of 16a–d by the diphenylpicrylhydrazyl (DPPH) assay showed IC50 values ranging from 7 to 32.3 μg/ml. Interaction of 16a, 16b, 16d–g with calf-thymus DNA (CT-DNA) was also supported by absorption titration studies. The compounds exhibit good binding propensity to CT-DNA and the DNA binding affinity (Kb) of the compounds varies as 16a; 16b; 16e; 16g > 16d; 16f. Interaction of 16d with CT-DNA was also investigated by fluorescence spectroscopy. The results support an intercalative interaction of 16d and 16f and non-intercalation mechanism for 16a, 16b, 16e, and 16g.

A 3, 9 - perylene dicarboxylic acid preparation method

The invention discloses a 3, 9 - perylene dicarboxylic acid of preparation method, specific step is ice-acetic acid in a solvent, in the dihydro e is obtained under the action of the sodium dichromate of 1, 8 - naphthalenedicarboxylic anhydride; 1, 8 - naphthalenedicarboxylic anhydride in saturated ammonia under the action of the acylation to obtain the 1, 8 - naphthalene asia amide; 1, 8 - naphthalene asia amide in potassium hydroxide and anhydrous sodium acetate manufacturing of the alkaline environment in the alkaline environment in C - C under high-temperature conditions obtained by coupling the 3, 4, 9, 10 - perylenetetracarboxylic acid diimide; 3, 4, 9, 10 - perylenetetracarboxylic acid diimide in under the action of the strong acid is converted into the 3, 4, 9, 10 - [...]; 3, 4, 9, 10 - [...] in microwave reactor in alkaline hydrolysis by the decarboxylation of 3, 9 - perylene dicarboxylic acid. The invention synthetic process more economic, environmental protection, high-efficient and simple.

Preparation method and application of novel perylene drug molecule with biological activity

The invention discloses a preparation method and application of a novel perylene drug molecule with the biological activity, and belongs to the technical field of medicine synthesis. According to thekey points of the technical scheme of the preparation method and application of the novel perylene drug molecule, the structural formula of the perylene drug molecule with the biological activity is as shown in the specification, wherein R is O or S. The invention further relates to the preparation method for the novel perylene drug molecule with the biological activity. The perylene drug moleculeprepared through the preparation method has good inhibitory activity on human cervical cancer hHela cells, human breast cancer MDA-MB-231 cells and human liver cancer HepG2 cells, is relatively low in toxicity on human normal cells and has the potential of becoming an anti-tumor drug.

Synthesis and Biological Evaluation of Organometallic Complexes Bearing Bis-1,8-naphthalimide Ligands

Organometallic N-heterocyclic carbene (NHC) complexes with intercalating bis-naphthalimide ligands were prepared and evaluated biologically. Cytotoxic effects against tumor cells or bacteria were strongly ligand dependent with minor influence of the metal (Ag, Ru, Rh, Au) centers. Complex 8b with a rhodium(I) NHC moiety was studied in more detail for its DNA interacting properties in comparison to the metal free ligand. These studies showed a good DNA binding pattern with some preference for the telomeric quadruplex structure hTelo. Complex 8b was also shown to trigger additional coordinative binding to the DNA and therefore represents an useful tool compound with a mixed intercalative/coordinative DNA binding mode.

Preparation method and application of novel perylene acid medicinal molecule with antineoplastic activity

The invention discloses a preparation method and application of a novel perylene acid medicinal molecule with antineoplastic activity, and belongs to the technical field of pharmaceutical synthesis. The novel perylene acid medicinal molecule with antineoplastic activity is characterized by having the structural formula as shown in the description. The invention also provides a preparation method of the novel perylene medicinal molecule with the antineoplastic activity. The prepared perylene medicinal molecule has higher inhibiting activity for human cervical carcinoma Hela cells, human breastcancer MDA-MB-231 cells and human liver cancer HepG2 cells, and has the potential of becoming an antineoplastic medicament.

Grinding imidation of anhydrides on smectite clays as recyclable and heterogeneous catalysts under solvent-free conditions

Imidation of various anhydrides employing solvent-free grindstone technique using smectite clays as recyclable and green catalysts was examined and obtained excellent yields.