3-Nitro-1,8-naphthalic anhydride

Base Information

• Chemical Name: 3-Nitro-1,8-naphthalic anhydride
• CAS No.: 3027-38-1
• Molecular Formula: C12H5NO5
• Molecular Weight: 243.175
• Hs Code.: 29163900
• European Community (EC) Number: 629-274-5
• NSC Number: 32326
• DSSTox Substance ID: DTXSID10184360
• Nikkaji Number: J236.690H
• Wikidata: Q83055292
• ChEMBL ID: CHEMBL2323376
• Mol file: 3027-38-1.mol

Synonyms:3-Nitro-1,8-naphthalic anhydride;3027-38-1;5-Nitrobenzo[de]isochromene-1,3-dione;3-Nitronaphthalic anhydride;NAPHTHALIC ANHYDRIDE, 3-NITRO-;5-Nitro-1H,3H-benzo[de]isochromene-1,3-dione;NSC 32326;BRN 0023762;1H,3H-Naphtho(1,8-cd)pyran-1,3-dione, 5-nitro-;7-nitro-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione;CHEMBL2323376;1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 5-nitro-;5-17-11-00495 (Beilstein Handbook Reference);MFCD00006926;SCHEMBL1565380;DTXSID10184360;NSC32326;BDBM50426885;NSC-32326;AKOS005173861;CS-W014647;3-Nitro-1,8-naphthalic anhydride, 95%;LS-95108;FT-0616216;3-Nitronaphthalene-1,8-dicarboxylic anhydride;F17151;3-Nitro-1,8-naphthalic anhydride, technical grade;5-Nitro-1H,3H-benzo[de]isochromene-1,3-dione #;5-nitro-1h,3h-naphtho[1,8-cd]pyran-1,3-dione;7-nitro-3-oxatricyclo[7.3.1.0^{5,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione

Chemical Property of 3-Nitro-1,8-naphthalic anhydride

Chemical Property:

• Appearance/Colour: Light yellow to beige or light brown powder
• Vapor Pressure: 4.12E-10mmHg at 25°C
• Melting Point: 247-249 °C (dec.)(lit.)
• Refractive Index: 1.742
• Boiling Point: 499.5 °C at 760 mmHg
• Flash Point: 256.4 °C
• PSA: 89.19000
• Density: 1.637 g/cm³
• LogP: 2.58180
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 243.01677226
• Heavy Atom Count: 18
• Complexity: 415

Purity/Quality:

98% ^*data from raw suppliers

3-Nitro-1,8-naphthalic anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=CC(=CC3=C2C(=C1)C(=O)OC3=O)[N+](=O)[O-]
• Uses: 3-Nitro-1,8-naphthalic anhydride is a reagent used to synthesize a monoboronic acid fluorescent sensor that exhibits emission suitable for ratiometric testing and also displays sensitivity for glucose relative to fructose and galactose. 3-Nitro-1,8-naphthalic anhydride is also used as a starting reagent in the synthesis of 5-substituted naphthalimide derivatives which exhibit high anti-cancer activity.

Technology Process of 3-Nitro-1,8-naphthalic anhydride

There total 3 articles about 3-Nitro-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: 94.0%

1,8-Naphthalic anhydride (81-84-5) → 3-nitro-1,8-naphthalic anhydride (3027-38-1)

Guidance literature:

With copper nitrate hemi(pentahydrate); acetic anhydride; acetic acid; at 40 ℃; for 5h;

Reference yield:

acenaphthene (83-32-9) → 3-nitro-1,8-naphthalic anhydride (3027-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1: nitric acid / 3 h / 50 °C

2: nitric acid; sulfuric acid / 0 °C

With sulfuric acid; nitric acid;

DOI:10.1016/j.bioorg.2020.104011

Reference yield:

→ 3-nitro-1,8-naphthalic anhydride (3027-38-1)

Guidance literature:

aus Naphthalin-1,8-dicarbonsaeureanhydrid;

DOI:10.1039/j39710003599

upstream raw materials:

1,8-Naphthalic anhydride

acenaphthene

Downstream raw materials:

6-nitro-1-naphthoic acid

3-nitro-1-naphthoic acid

2,4,6-Trimethyl-N-((R)-1-methyl-2-{2-[(R)-2-(5-nitro-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-propylamino]-ethylamino}-ethyl)-benzenesulfonamide

methyl 6-nitro-1-naphthoate

Refernces

• 1、 Xie, Song-Qiang,Zhang, Ya-Hong,Li, Qian,Xu, Feng-Hua,Miao, Jiu-Wang,Zhao, Jin,Wang, Chao-Jie. "3-Nitro-naphthalimide and nitrogen mustard conjugate NNM-25 induces hepatocellular carcinoma apoptosis via PARP-1/p53 pathway". . p. 725 - 734. Retrieved 2012.
• 2、 -. "Naphthalimide-polyamine conjugate as well as preparation method and application thereof". Paragraph 0030; 0108-0110; 0113. . Retrieved 2021/02/10.
• 3、 -. "Naphthalimide indole heterocyclic compound as well as preparation method and application thereof". Paragraph 0056; 0059; 0063-0065; 0069-0071; 0075-0076;...... . Retrieved 2021/06/06.