1,8-Naphthalimide

Base Information

• Chemical Name: 1,8-Naphthalimide
• CAS No.: 81-83-4
• Molecular Formula: C12H7NO2
• Molecular Weight: 197.193
• Hs Code.: 29251995
• European Community (EC) Number: 201-379-7
• NSC Number: 11011
• UNII: GI0TV19GBN
• DSSTox Substance ID: DTXSID0044731
• Nikkaji Number: J3.863F
• Wikidata: Q27279115
• ChEMBL ID: CHEMBL339586
• Mol file: 81-83-4.mol

Synonyms:Naphthalimide;Naphthalimides

Chemical Property of 1,8-Naphthalimide

Chemical Property:

• Appearance/Colour: off-white to white powder
• Vapor Pressure: 2.41E-13mmHg at 25°C
• Melting Point: 299-300 °C(lit.)
• Refractive Index: 1.696
• Boiling Point: 449.1 °C at 760 mmHg
• PKA: 9.48±0.20(Predicted)
• Flash Point: 208.9 °C
• PSA: 49.93000
• Density: 1.391 g/cm³
• LogP: 1.47930
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 197.047678466
• Heavy Atom Count: 15
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

1,8-Naphthalimide >98.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C3C(=C1)C(=O)NC(=O)C3=CC=C2
• Uses: It is a useful material for utilization in phosphorescence dye doped organic light emitting diodes (oleds), hole blocking and electron-conducting material.

Technology Process of 1,8-Naphthalimide

There total 45 articles about 1,8-Naphthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,8-Naphthalic anhydride (81-84-5) → 1,8-Naphthalimide (81-83-4)

Guidance literature:

With ammonium hydroxide; In ethanol; at 70 ℃; for 12h; Sealed tube;

DOI:10.1016/j.bioorg.2021.104859

Reference yield: 75.0%

sodium cyanide (773837-37-9) + acenaphthene quinone (82-86-0) → 1,8-Naphthalimide (81-83-4) + 1,8-Naphthalic anhydride (81-84-5) + 1-hydroxy-2-oxo-1-acenaphthylene-1-carbonitrile (69517-48-2)

Guidance literature:

With oxygen; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.crci.2015.07.007

Reference yield: 57.0%

trimethylsilyl isocyanate (1118-02-1) + naphthalene-1-carbonic acid chloride (879-18-5) → 1,8-Naphthalimide (81-83-4)

Guidance literature:

aluminium trichloride; In various solvent(s); at 90 ℃; for 1h;

upstream raw materials:

1,8-Naphthalic anhydride

acenaphthenequinone monoxime

Naphthalene-1,8-dicarboxylic acid

8-carbamoyl-[1]naphthoic acid

Downstream raw materials:

2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

1,8-naphtholactam

2,3-dihydro-1H-benzo[de]isoquinoline

3,4,9,10-perylene tetracarboxyxlic acid diimide

Refernces

• 1、 Sheshashena Reddy,Ram Reddy. "Synthesis and fluorescence study of naphthalimide-coumarin, naphthalimide-luminol conjugates". . p. 1571 - 1580. Retrieved 2014.
• 2、 Liu, Luxiao,Zhang, Hong-Yu,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan. "Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea". . p. 1351 - 1357. Retrieved 2019/11/19.