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
• Article Data: 4

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

Chemical Properties

light yellow powder

Uses

3-Nitrophthalonitrile can be used in solar cells. Dyes and metabolites.

Application

3-Nitrophthalonitrile belongs to nitrile derivatives and can be used as pesticide and pharmaceutical intermediates. It is an important intermediate for the synthesis of nitrophthalocyanine, nitrometallophthalocyanine or other phthalocyanine derivatives.

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

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

Downstream Products

• 61109-17-9 2,3-dicyano-N,N-dimethylaniline 
• 19056-23-6 3-methoxybenzene-1,2-dicarbonitrile 
• 77474-62-5 1,2-dicyano-3-phenoxybenzene 
• 51762-68-6 3-(phenylthio)-phthalonitrile 
• 130107-88-9 (R,S)-1,2-dicyano-3-(2-ethylhexyloxy)benzene 
• 201480-81-1 3-(4-tert-butylphenoxy)phthalonitrile 
• 60016-67-3 3,3'-[4,4'-(propane-2,2-diyl)bis(4,1-phenylene)]bis(oxy)diphthalonitrile 
• 760206-85-7 3-[4-(bromomethyl)phenoxy]phthalonitrile 
• 760206-83-5 3-[4-(methansulfonylmethyl)phenoxy]phthalonitrile 
• 159189-27-2 3-(imidazol-2-ylthio)phthalodinitrile 
• 919766-59-9 serinol bisphthalonitrile 

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.

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).