51762-67-5

Basic information

• Product Name: 3-Nitrophthalonitrile
• Synonyms: 2,3-DICYANONITROBENZENE;1,2-DICYANO-3-NITROBENZENE;3-NITRO-PHTHALODINITRILE;3-NITROPHTHALONITRILE;3-nitro-1,2-benzenedicarbonitrile;3-nitro-2-benzenedicarbonitrile;2,3-Dicyano-1-nitrobenzene;Nitrophthalonitrile
• CAS NO: 51762-67-5
• Molecular Formula: C₈H₃N₃O₂
• Molecular Weight: 173.13
• EINECS: -0
• Product Categories: Aromatic Nitriles;Benzene derivates;Functional Materials;Phthalonitriles & Naphthalonitriles;Phthalonitriles (Building Blocks for Phthalocyanines);N;Stains and Dyes;Stains&Dyes, A to
• Mol File: 51762-67-5.mol

Chemical Properties

• Melting Point: 162-165 °C(lit.)
• Boiling Point: 386.1 °C at 760 mmHg
• Flash Point: 187.3 °C
• Appearance: light yellow powder
• Density: 1.41 g/cm³
• Vapor Pressure: 3.63E-06mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: room temp
• Water Solubility: Soluble in methanol. Insoluble in water.
• BRN: 2263686
• CAS DataBase Reference: 3-Nitrophthalonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitrophthalonitrile(51762-67-5)
• EPA Substance Registry System: 3-Nitrophthalonitrile(51762-67-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36-45-37/39
• WGK Germany: 3
• RTECS: CZ1953200
• Hazardous Substances Data: 51762-67-5(Hazardous Substances Data)

Usage

Uses

Used in Solar Cells:
3-Nitrophthalonitrile is used as a key component in the development of solar cells due to its ability to enhance the efficiency and performance of these energy-harvesting devices.
Used in Dyes and Metabolites:
3-Nitrophonitrile serves as an intermediate in the production of various dyes and metabolites, contributing to the diversity and functionality of these compounds in different industries.
Used in Pesticide Industry:
3-Nitrophthalonitrile is used as a pesticide intermediate, playing a crucial role in the development of effective and environmentally friendly pest control solutions.
Used in Pharmaceutical Industry:
3-Nitrophthalonitrile is utilized as a pharmaceutical intermediate, contributing to the synthesis of various drugs and medications that address a wide range of health issues.

Preparation

The synthesis of 3-nitrophthalonitrile started with the nitration in position 3 of phthalimide followed by the formation of 3-nitrophthalamide; then dehydration by the thionyl chloride in N, N-dimethylformamide leads to 3-nitrophthalonitrile.Synthesis of 3-Nitrophthalonitrile

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 32, p. 495, 1995 DOI: 10.1002/jhet.5570320219

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

Upstream product

• 24564-71-4 3-Nitrophthaloyl dichloride 
• 91-15-6 phthalonitrile 
• 96385-50-1 3-nitrophthalamide 
• 75-44-5 phosgene 
• 603-11-2 3-nitrophthalic acid 

Downstream Products

• 130107-86-7 3-(2,4-dimethyl-3-pentyloxy)phthalonitrile 
• 60016-67-3 3,3'-[4,4'-(propane-2,2-diyl)bis(4,1-phenylene)]bis(oxy)diphthalonitrile 
• 19056-23-6 3-methoxybenzene-1,2-dicarbonitrile 
• 243144-84-5 3-(2-ferrocenylethoxy)phtalonitrile 
• 853309-16-7 3-[5-methyl-2-(propan-2-yl)phenoxy]benzene-1,2-dicarbonitrile 
• 201480-81-1 3-(4-tert-butylphenoxy)phthalonitrile 
• 797757-63-2 2,7-di-tert-butyl-9,9-bis(2,3-dicyanophenoxymethyl)fluorene 
• 649553-08-2 3-[4-(hydroxymethyl)phenoxy]phthalonitrile 
• 277309-61-2 1,2-dicyano-3-propylthiobenzene 

Relevant articles and documents

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 3-Nitrophthalonitrile and Tetra-α-substituted

An efficient synthesis of phthalocyanines prepared from ortho-substituted phthalonitriles is described.The precursor to these phthalocyanines, 3-nitrophthalonitrile, is a key reagent for syntheses of phthalonitriles substituted at the 3-position by means of nucleophilic aromatic substitutions.An example of this type of phthalocyanine, prepared from 3-(4-cumylphenoxy)phthalonitrile, is compared with the phthalocyanine derived from 4-(4-cumylphenoxy)phthalonitrile.Substitution of the phthalocyanine at this more sterically crowded site causes a 20 nm bathochromic shift of the Q-band (?-?* transition).

Carboxylic acids and derivates thereof

Carboxylic acids and derivatives having a general formula X-O-Ar-O-Y in which X and Y are aromatic mono or di-basic carboxylic acid groups of derivatives which may be the same or different. Ar is a divalent aromatic group having at least one tertiary alkyl substituent and not more than one such substituent ortho to each of its bonds to the ether groups. A polyetherimide is prepared by reacting an anhydride derivative of the above formula with a diamine. Gas separation membranes can be fabricated from the resultant polyetherimides.