4-Amino-1,8-naphthalic anhydride

Base Information

• Chemical Name: 4-Amino-1,8-naphthalic anhydride
• CAS No.: 6492-86-0
• Molecular Formula: C12H7NO3
• Molecular Weight: 213.192
• Hs Code.: 2932999099
• European Community (EC) Number: 229-372-4
• NSC Number: 7564
• DSSTox Substance ID: DTXSID10215229
• Nikkaji Number: J8.415H
• Wikidata: Q72439871
• ChEMBL ID: CHEMBL2323375
• Mol file: 6492-86-0.mol

Synonyms:6492-86-0;4-Amino-1,8-naphthalic anhydride;6-Aminobenzo[de]isochromene-1,3-dione;Naphthalic anhydride, 4-amino-;1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-amino-;6-amino-1h,3h-benzo[de]isochromene-1,3-dione;CHEMBL2323375;4-Aminonaphthalene-1,8-dicarboxylic anhydride;4-Amino-1.8-naphthalic anhydride;EINECS 229-372-4;MFCD00009776;8-amino-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione;1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 6-amino-;NSC7564;SCHEMBL1025154;DTXSID10215229;BCP10398;NSC 7564;NSC-7564;BDBM50426886;AKOS003247522;AC-6718;CS-W006543;1H,8-cd]pyran-1,3-dione, 6-amino-;4-Amino-1,8-naphthalic anhydride, 95%;AS-19655;SY107333;FT-0636166;10-amino-3-oxatricyclo[7.3.1.0?,??]trideca-1(13),5,7,9,11-pentaene-2,4-dione;8-amino-3-oxatricyclo[7.3.1.0^{5,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione

Chemical Property of 4-Amino-1,8-naphthalic anhydride

Chemical Property:

• Appearance/Colour: Orange powder
• Vapor Pressure: 3.49E-10mmHg at 25°C
• Melting Point: 360 °C
• Refractive Index: 1.77
• Boiling Point: 501.4 °C at 760 mmHg
• PKA: 1.15±0.20(Predicted)
• Flash Point: 310.8 °C
• PSA: 69.39000
• Density: 1.534 g/cm³
• LogP: 2.31380
• Storage Temp.: −20°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 213.042593085
• Heavy Atom Count: 16
• Complexity: 341

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Amino-1,8-naphthalic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-20/21/22-36/37/38
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=CC3=C2C(=C1)C(=O)OC3=O)N

Technology Process of 4-Amino-1,8-naphthalic anhydride

There total 10 articles about 4-Amino-1,8-naphthalic anhydride 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: 98.0%

4-nitronaphthalic-1,8-anhydride (6642-29-1) → 4-amino-1,8-naphthalic anhydride (6492-86-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 40 ℃; under 7500.75 Torr;

DOI:10.1039/c5ob00751h

Reference yield: 81.4%

6-azido-1H,3H-benzo[de]isochromene-1,3-dione (1262149-88-1) → 4-amino-1,8-naphthalic anhydride (6492-86-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In N,N-dimethyl-formamide; at 20 ℃; for 36h;

DOI:10.1039/c5ob00302d

Reference yield: 81.0%

4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → 4-amino-1,8-naphthalic anhydride (6492-86-0)

Guidance literature:

4-bromo-1,8-naphthalenedicarboxylic anhydride; With sodium azide; In water; N,N-dimethyl-formamide; at 80 ℃; for 2h;

With sodium hydrogensulfide; In water; N,N-dimethyl-formamide; at 90 ℃; for 2h;

DOI:10.1039/d0cc05335j

upstream raw materials:

4-nitronaphthalic-1,8-anhydride

hydrogenchloride

4-nitroacenaphthene

acenaphthene

Refernces

• 1、 Jolley, Elizabeth A.,Hardebeck, Laura K.E.,Ren, Yi,Adams, Miranda S.,Lewis, Michael,Znosko, Brent M.. "The effects of varying the substituent and DNA sequence on the stability of 4-substituted DNA-naphthalimide complexes". . p. 29 - 37. Retrieved 2018.
• 2、 Zhang, Hengrui,Fang, Zhijie. "A novel glutathione-Triggered theranostic prodrug for anticancer and imaging in living cells". . p. 11419 - 11423. Retrieved 2018.
• 3、 Yang, Jun,Xie, Bo,Bai, Jing,Yang, Qing. "Purification and characterization of a nitroreductase from the soil bacterium Streptomyces mirabilis". . p. 720 - 724. Retrieved 2012.
• 4、 Ma, Jing,Li, Linrong,Yue, Kexin,Zhang, Zhansheng,Su, Shihao,Chen, Yutong,Yu, Lu,Zhang, Pengfei,Ma, Ruijuan,Li, Yingguang,Ma, Yinxia,Jia, Huinan,Wang, Chaojie,Wang, Jiajia,Xie, Songqiang. "A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent". supporting information. . Retrieved 2021/05/10.