602-60-8

Basic information

• Product Name: 9-NITROANTHRACENE
• Synonyms: 9-Nitroanthracene,97%;5-Nitroanthracene;9-nitro-anthracen;Anthracene,9-nitro-;LABOTEST-BB LT02096509;9-NITROANTHRACENE;9-Nitroanthracene (purity);88993, 9-Nitroanthracene (purity)
• CAS NO: 602-60-8
• Molecular Formula: C₁₄H₉NO₂
• Molecular Weight: 223.23
• EINECS: 210-021-9
• Product Categories: Alphabetic;Environmental CRM;N;NA - NIApplication CRMs;Nitro-PAH;Miscellaneous;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 602-60-8.mol
• Article Data: 31

Chemical Properties

• Melting Point: 141-144 °C(lit.)
• Boiling Point: 275°C 17mm
• Flash Point: 275°C/17mm
• Appearance: /
• Density: 1.1814 (rough estimate)
• Vapor Pressure: 1.16E-06mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: 2-8°C
• BRN: 1877509
• CAS DataBase Reference: 9-NITROANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 9-NITROANTHRACENE(602-60-8)
• EPA Substance Registry System: 9-NITROANTHRACENE(602-60-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: CB0715000
• Hazardous Substances Data: 602-60-8(Hazardous Substances Data)

Usage

Description

9-NITROANTHRACENE is a yellow solid that serves as a crucial precursor in the synthesis of various compounds, particularly anthraquinones. These anthraquinones have a wide range of applications, including their use as photosensitizers in photodynamic therapy (PDT) and as key components in the development of pharmaceutical drugs.

Uses

Used in Photodynamic Therapy (PDT):
9-NITROANTHRACENE is used as a precursor for anthraquinones, which are employed as photosensitizers in PDT. The application reason is that these anthraquinones can effectively absorb light and generate reactive oxygen species, leading to the destruction of cancerous cells upon light activation.
Used in Pharmaceutical Industry:
9-NITROANTHRACENE is used as a starting material for the synthesis of various drugs, such as Emodin (E523000), Aloe-emodin (A575400), and Rufgallol. The application reason is that these drugs have demonstrated potential therapeutic effects in treating different health conditions, including cancer.
Used in Cancer Therapy:
9-NITROANTHRACENE has potential applications in cancer therapy due to its role in the production of anthraquinones, which can be utilized in PDT and the development of anticancer drugs. The application reason is that these anthraquinones and derived drugs can target and eliminate cancer cells, offering a promising avenue for cancer treatment.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aromatic nitro compounds, such as 9-NITROANTHRACENE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. 9-NITROANTHRACENE may be sensitive to prolonged exposure to light.

Health Hazard

ACUTE/CHRONIC HAZARDS: 9-NITROANTHRACENE may cause skin irritation on contact.

Fire Hazard

Flash point data are not available for 9-NITROANTHRACENE, but 9-NITROANTHRACENE is probably combustible.

Purification Methods

Purify it by recrystallisation from EtOH or MeOH. Further purify it also by sublimation or TLC. [Beilstein 5 H 666, 5 II 578, 5 III 2136, 5 IV 2296.]

InChI:InChI=1/C14H9NO2/c16-15(17)14-7-3-6-12-8-10-4-1-2-5-11(10)9-13(12)14/h1-9H

Upstream product

• 6596-35-6 tetradecahydroanthracene 
• 84305-14-6 9-ethoxy-10-nitro-9,10-dihydroanthracene 
• 92856-25-2 acetic acid-(10-nitro-9,10-dihydro-[9]anthryl ester) 
• 67-66-3 chloroform 
• 120-12-7 anthracene 
• 10544-72-6 dinitrogen tetraoxide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 110-86-1 pyridine 
• 7697-37-2 nitric acid 
• 98-95-3 nitrobenzene 
• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 7664-93-9 sulfuric acid 

Downstream Products

• 90-44-8 anthracen-9(10H)-one 
• 523-27-3 9,10-Dibromoanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 84457-22-7 10-nitro-9-methylanthracene 
• 10496-15-8 dihexyl disulfide 
• 74851-73-3 9-anthrylhexylsulfide 
• 629-45-8 dibutyl disulfide 
• 74851-71-1 aci-9,9'-dinitro-10,10'-dihydro-10,10'-bianthryl 
• 98-46-4 3-trifluoromethylnitrobenzene 
• 150-60-7 dibenzyl disulphide 
• 1210-12-4 9-cyanoanthracene 
• 642-31-9 9-anthracene aldehyde 
• 529-86-2 9-anthrol 
• 434-84-4 bianthronyl 

Relevant articles and documents

SELECTIVE OXIDATION OF ANTHRACENE TO ANTHRAQUINONE IN ACETIC ACID WITH AIR IN PRESENCE OF NITRIC ACID

The oxidation of anthracene in acetic acid with air in the presence of small proportion of nitric acid produced high quality anthraquinone with acceptable yields.A possible mechanism is suggested which explains the predominance of the oxidation reaction compared with that of nitration.

Tetranitroethylene. In Situ Formation and Diels-Alder Reactions

The reaction of hexanitroethane with dienes gave the Diels-Alder adducts of tetranitroethylene.Thus, the reaction in refluxing benzene of hexanitroethane with anthracene gave 11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene.Similarly, 9-methylanthracene and 9,10-dimethylanthracene gave 9-methyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene and 9,10-dimethyl-11,11,12,12-tetranitro-9,10-dihydro-9,10-ethanoanthracene, respectively.Cyclopentadiene reacted with hexanitroethane in methylene chloride at -10 deg C to give 5,5,6,6-tetranitro-2-norbornene.Reaction of the anthracene adduct of tetranitroethylene with sodium iodide gave the sodium salt of 12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, which was protonated with acetic acid to give the corresponding nitro ketone.Treatment of the sodium salt with clorine and bromine gave 12-chloro-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one and 12-bromo-12-nitro-9,10-dihydro-9,10-ethanoanthracen-11-one, respectively.

NITRATION

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.

Nitration of arenes by 1-sulfopyridinium nitrate as an ionic liquid and reagent by in situ generation of NO2

1-Sulfopyridinium nitrate was synthesized as a potent nitrating agent for the nitration of arenes without the need for any co-catalysts. A variety of nitro compounds were synthesized and fully characterized by IR, 1H NMR, 13C NMR, thermal gravimetric analysis (TGA), differential thermal gravimetry (DTG), CHN analysis and mass spectroscopy. Mechanistically, in situ generated nitrogen dioxide as a radical from the reagent is proposed for the presented nitration protocol.

Phosphoric acid modified montmorillonite clay: A new heterogeneous catalyst for nitration of arenes

The easily available montmorillonite clay is treated with phosphoric acid and 10 wt.% is found to be the optimum concentration of phosphoric acid that can be adsorbed chemically on the surface of the clay. Acidity of this phosphoric acid treated montmorillonite clay (PAM) is determined by volumetric as well as potentiometric titration and characterized. Catalytic efficacy of PAM in nitration of various aromatic compounds is reported.