9-Nitroanthracene

Base Information

• Chemical Name: 9-Nitroanthracene
• CAS No.: 602-60-8
• Molecular Formula: C14H9 N O2
• Molecular Weight: 223.231
• European Community (EC) Number: 210-021-9
• NSC Number: 47175
• UNII: JZ1TB3N57P
• DSSTox Substance ID: DTXSID5025730
• Nikkaji Number: J2.731F
• Wikidata: Q27156005
• ChEMBL ID: CHEMBL166112
• Mol file: 602-60-8.mol

Synonyms:9-nitroanthracene

Chemical Property of 9-Nitroanthracene

Chemical Property:

• Vapor Pressure: 1.16E-06mmHg at 25°C
• Melting Point: 141-144 °C(lit.)
• Refractive Index: 1.4700 (estimate)
• Boiling Point: 275°C 17mm
• Flash Point: 275°C/17mm
• PSA: 45.82000
• Density: 1.316g/cm³
• LogP: 4.42440
• Storage Temp.: 2-8°C
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 223.063328530
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

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

9-Nitroanthracene ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Polycyclic Aromatic Hydrocarbons
• Canonical SMILES: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2[N+](=O)[O-]
• Uses: 9-nitroanthracene is a precursor of anthraquinones, which are often used as photosensitizers used in photodynamic therapy (PDT). Anthraquinone is also an important precursor for drugs such as Emodin (E523000), Aloe-emodin (A575400), and Rufgallol. 9-nitroanthracene has potential application in cancer therapy.

Technology Process of 9-Nitroanthracene

There total 52 articles about 9-Nitroanthracene 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: 95.0%

anthracene (120-12-7) → 9-nitroanthracene (602-60-8)

Guidance literature:

With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃;

DOI:10.1081/SCC-100103545

Reference yield: 67.0%

9-Chloro-10-nitroanthracene (66670-30-2) → 9-nitroanthracene (602-60-8)

Guidance literature:

With sodium hydroxide; In water; at 70 ℃; for 0.25h;

DOI:10.1016/j.bmc.2014.03.045

Reference yield: 63.0%

hexanitroethane (918-37-6) + anthracene (120-12-7) → 9-nitroanthracene (602-60-8) + 11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene (73804-83-8)

Guidance literature:

In benzene; for 0.5h; Heating;

DOI:10.1021/jo01302a024

upstream raw materials:

pyridine

ethanol

9,10-dihydro-9,10-dinitroanthracene

9-ethoxy-10-nitro-9,10-dihydroanthracene

Downstream raw materials:

anthracen-9(10H)-one

9,10-Dibromoanthracene

9,10-phenanthrenequinone

9-Cyclohexyl-10-nitro-anthracene

Refernces

• 1、 Pryor, William A.,Gleicher, Gerald J.,Cosgrove, John P.,Church, Daniel F.. "Reaction of Polycylic Aromatic Hydrocarbons (PAH) with Nitrogen Dioxide in Solution. Support for an Electron-Transfer Mechanism of Aromatic Nitration Based on Correlations Using Simple Molecular Orbital Theory". . p. 5189 - 5194. Retrieved 1984.
• 2、 Hong, Chen,Luo, Wen,Yao, Dong,Su, Ya-Bin,Zhang, Xin,Tian, Run-Guo,Wang, Chao-Jie. "Novel aromatic-polyamine conjugates as cholinesterase inhibitors with notable selectivity toward butyrylcholinesterase". . p. 3213 - 3219. Retrieved 2014.
• 3、 Saikia, Susmita,Borah, Ruli. "2-Methyl-1,3-disulfoimidazolium polyoxometalate hybrid catalytic systems as equivalent safer alternatives to concentrated sulfuric acid in nitration of aromatic compounds". . . Retrieved 2019/08/20.
• 4、 Zanardi, María M.,Suárez, Alejandra G.. "Synthesis of new chiral 1,3-aminoalcohols derived from levoglucosenone and their application in asymmetric alkylations". supporting information. p. 3762 - 3765. Retrieved 2015/06/08.