33224-18-9

Basic information

• Product Name: 3,5-DICYANONITROBENZENE
• Synonyms: 3,5-DICYANONITROBENZENE;5-nitroisophthalonitrile
• CAS NO: 33224-18-9
• Molecular Formula: C₈H₃N₃O₂
• Molecular Weight: 173.12832
• Mol File: 33224-18-9.mol

Chemical Properties

• Boiling Point: 279.6 °C at 760 mmHg
• Flash Point: 122.9 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 0.00399mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 3,5-DICYANONITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DICYANONITROBENZENE(33224-18-9)
• EPA Substance Registry System: 3,5-DICYANONITROBENZENE(33224-18-9)

Safety Data

• Hazardous Substances Data: 33224-18-9(Hazardous Substances Data)

Usage

Uses

Used in Dye and Pigment Manufacturing:
3,5-Dicyanonitrobenzene is used as a key intermediate in the production of dyes and pigments for various applications, including textiles, plastics, and printing inks. Its ability to undergo chemical reactions allows for the creation of a wide range of colorants with different properties.
Used in Pharmaceutical Industry:
3,5-Dicyanonitrobenzene is utilized as a starting material in the synthesis of various pharmaceutical compounds. Its reactivity and capacity to form derivatives make it a valuable component in the development of new drugs with specific therapeutic properties.
Used in Chemical Research:
Due to its ability to participate in multiple chemical reactions, 3,5-Dicyanonitrobenzene is also employed in chemical research for studying reaction mechanisms, exploring new synthetic pathways, and developing novel compounds with potential applications in various fields.

InChI:InChI=1/C8H3N3O2/c9-4-6-1-7(5-10)3-8(2-6)11(12)13/h1-3H

Upstream product

• 50826-03-4 3-cyano-5-nitro-benzoic acid amide 
• 38177-07-0 5-nitro-1,3-benzenedicarboxamide 
• 13438-30-7 5-nitro-1,3-benzenedicarbonylchloride 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 618-88-2 5-nitrobenzene-1,3-dicarboxylic acid 
• 23218-93-1 3-amino-5-nitro-benzoic acid methyl ester 
• 99066-80-5 methyl 3-cyano-5-nitrobenzoate 

Downstream Products

• 111902-85-3 C₁₂H₉ClN₃O₄^(1-)*Na⁽¹⁺⁾ 
• 20033-48-1 1-amino-2,6-dicyano-4-nitrobenzene 
• 101-63-3 bis(4-nitrophenyl)ether 
• 79370-78-8 5-hydroxyisophthalonitrile 
• 188998-65-4 5-(4-Nitro-phenoxy)-isophthalonitrile 
• 188998-64-3 5-(4-Cyano-phenoxy)-isophthalonitrile 

Relevant articles and documents

Corresponding amine nitrile and method of manufacturing thereof

The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Corresponding amine nitrile and method of manufacturing thereof (by machine translation)

The invention relates to a method of manufacturing one kind of nitrile, compared with the prior art, has significantly reduced the amount of ammonia, the environmental pressure of the small, low energy consumption, low production cost, nitrile product purity and yield and the like, and can obtain more complex structure of the nitriles. The invention also relates to the corresponding amine by the nitrile manufacture method. (by machine translation)

Formation constants in C-H hydrogen bonding. 4. Effects of cyano, nitro, and trifluoromethyl substituents in aromatic compounds

Formation constants ( Keq) have been measured using 1H NMR for H-bond complexes with HMPA in CCl 4of 35 aromatic compounds variously substituted with cyano, nitro, and trifluoromethyl groups; several compounds contained F and Cl. The three strongly polar groups enhance H-bonding significantly, usually in the order NO2 > CN > CF3; all are superior to Cl and F. 1,3,5-Trinitrobenzene fails to H-bond at all; however, TNT, its tert-butyl analog, and trinitro-m-xylene show significant Keq values. Coplanarity of nitro groups with the ring blocks approach of HMPA, probably via intramolecular H-bonds. The buttressing effect is evident in some crowded compounds.

Synthesis and photophysical properties of 2,6-dicyano-p-phenylenediamine

The photophysical and electrochemical properties of p-phenylenediamine (PPD) are strongly affected by the addition of cyano groups to the aromatic ring. In 2,3,5,6-tetracyano-p-phenylenediamine (TCPPD) the photophysics is governed mostly by the solvent basicity (β) whereas in 2,6-dicyano-N,N, N′,N′-tetramethyl-p-phenylenediamine (DCTMPPD) by the solvent polarity/polarizability (π*). In order to study the interactions of cyano-substituted PPDs with the solvent molecules in more detail as well as to clarify the role and origin of hydrogen bonding differences for TCPPD and DCTMPPD, another cyano substituted PPD, 2,6-dicyano-p-phenylenediamine (DCPPD) has been synthesized. The photophysical properties have been measured in a wide range of solvents. The fluorescence lifetimes (from 14 ns to 20 ns) and quantum yields (from 0.7 to 0.85) are not very sensitive to the environment. The solvatochromism is analyzed by a linear solvation energy relationship (LSER) using parameters developed by Kamlet, Taft and co-workers. It has been found that both absorption and emission of DCPPD depend on specific as well as non-specific interactions of the solute with the solvent molecules. The ground and excited state pKa values for DCPPD have also been determined.

Water-induced fluorescence quenching of mono- and dicyanoanilines

Photophysical properties of monocyano- (2-, 3-, and 4-cyano) and dicyano- (3,4-, 3,5-, 2,3-, 2,4-, 2,5-, and 2,6-dicyano) anilines are investigated by fluorescence measurements. All the monocyanoanilines are virtually nonfluorescent in water (quantum yield 0.01); however, in nonaqueous solvents (cyclohexane, acetonitrile and ethanol), the fluorescence quantum yield is enhanced substantially. In contrast, dicyanoanilines investigated are highly fluorescent both in aqueous and nonaqueous environments. The photophysical data and MO calculations suggest that conformational changes in the amino group and variation of hydrogen-bonding interactions between the solute and solvent water upon electronic excitation are responsible for the water quenching in the monocyanoanilines.

Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and molecular oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodology based on nitric and sulfuric acids. In some cases, the minor isomer became favoured to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products.

Synthesis of 5-Aryloxyisophthalonitriles by Nitro Group Substitution in 5-Nitrosophthalonitrile under the Action of Phenols

A series of 5-aryloxyisophthalodinitrile is obtained by the nitro group substitution in the reaction of either unsubstituted phenole, or substituted phenoles with 5-nitroisophthalodinitrile in the presence of potassium carbonate in DMF or in toluene under conditions of phase-transfer catalysis.

Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series

53 Donor-acceptor substituted azo dyes of the benzene series were prepared by diazonium-coupling reactions (1a-s) or halogen-cyanide exchange (->2a-x, 3a-j).Described are the preparation of the amines 4a-m and the coupling compounds 5a-t and the procedure of diazotizing and coupling.The colouristic and spectroscopic data show that compounds of the general formula 1 are excellent brilliant blue azo dyes usefull for dyeing polyester material.