31643-49-9

Basic information

• Product Name: 5-Nitrobenzene-1,2-dicarbonitrile
• Synonyms: 4-nitro-2-benzenedicarbonitrile;4-nitro-phthalonitril;4-NITRO-1,2-BENZENE DICARBONITRILE;4-NITRO-1,2-DICYANOBENZENE;4-NITRO-O-BENZENEDINITRILE;4-NITROBENZENE-1,2-DINITRILE;4-NITROPHTHALIC ACID DINITRILE;4-NITROPHTHALONITRILE
• CAS NO: 31643-49-9
• Molecular Formula: C₈H₃N₃O₂
• Molecular Weight: 173.13
• EINECS: 250-748-9
• Product Categories: Fluorobenzene;Aromatic Nitriles;Benzene derivates;Nitriles;Functional Materials;Phthalonitriles & Naphthalonitriles;Phthalonitriles (Building Blocks for Phthalocyanines);N;Stains and Dyes;Stains&Dyes, A to;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Aromatic
• Mol File: 31643-49-9.mol

Chemical Properties

• Melting Point: 142-144 °C(lit.)
• Boiling Point: 303.75°C (rough estimate)
• Flash Point: 189.6 °C
• Appearance: Light yellow, light greenish or light gray to beige/Crystalline Powder, Crystals and/or Chunks
• Density: 1.4553 (rough estimate)
• Vapor Pressure: 2.76E-06mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
• BRN: 1877554
• CAS DataBase Reference: 5-Nitrobenzene-1,2-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Nitrobenzene-1,2-dicarbonitrile(31643-49-9)
• EPA Substance Registry System: 5-Nitrobenzene-1,2-dicarbonitrile(31643-49-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: TI8576000
• TSCA: Yes
• Hazardous Substances Data: 31643-49-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-Nitrobenzene-1,2-dicarbonitrile is used as an intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for the creation of a wide range of molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Dye Production:
In the dye industry, 5-Nitrobenzene-1,2-dicarbonitrile is utilized as a key component in the production of various dyes. Its chemical properties enable the development of dyes with specific color characteristics and stability, making it a valuable asset in this application.
Used in Metabolite Research:
5-Nitrobenzene-1,2-dicarbonitrile is also employed in the study of metabolites, which are the byproducts of cellular processes. Its use in this field aids in the understanding of metabolic pathways and the development of targeted therapies for various diseases.

Preparation

Synthesis of 4-Nitrophthalonitrile: SOCl2 (83.5 mL. 1.144 mol) was added dropwise under nitrogen purge to dry DMF (200 mL) which had been cooled to 0-5 °C. The solution was allowed to stir for 15 min at 0-5 °C. The 4-nitrophthalamide (60.1 g, 0.286 mol) was then added and the solution was allowed to slowly warm to room temperature and react for 18 h under nitrogen purge. The solution was then slowly added to ice water to crystallize and precipitate the product. The 4-nitrophthalonitrile was collected using vacuum filtration, washed with ice cold water, and allowed to air dry overnight; yield: 45.2 g (92%); m.p.: 141 °C (det. by DSC) 1 H NMR((CD3)2SO): 8.41 (dd, 1H), 8.67 (dd, 1H), 9.03 (dd, 1H) FTIR: 3091 (m, aromatic C-H stretch), 2242 (d, CN stretch), 1534 (s, asymmetric N=O stretch), 1349 (s, symmetric N=O stretch), 853 (s, C-N stretch)

Synthesis

4-Nitrophthalonitrile synthesized from phthalimide in three steps. The reaction time of ruthenium chloride and HZSM-5 catalysts was very shorter than ammonium molybdate and Hβ catalysts. The yield while we used ruthenium chloride and HZSM-5 catalysts were very higher than another.In a three necked flask, 70 mL of dry dimethylformamide (DMF) was cooled to 0 °C under a stream of nitrogen and 7.3 mL of thionyl chloride was added so that the internal temperature did not go beyond 5 °C. After addition, nitrogen flow was ceased and a calcium chloride tube was added to the top of flask. Meanwhile, the color of the medium was observed to be yellow. Then, 10 g (0.048 mol) of 4- nitrophthalamide was slowly added so that the internal temperature did not go beyond 5 °C. The mixture was stirred over ice bath for 1 hour. The mixture was stirred at room temperature for 2 hours and then poured over 500 g of ice-water. The precipitate was filtered and washed successively with water, 250 mL 5% sodium hydrogencarbonate solution, and water again and dried in a vacuum oven at 110-120 °C. Molecular formula: C8H3N3O2. Yield: 7.4 g (90%). Mp: 141 °C.

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

Upstream product

• 13138-53-9 4-nitrophthalic amide 
• 108-24-7 acetic anhydride 
• 91-15-6 phthalonitrile 
• 1033995-63-9 oxonium 
• 136918-14-4 phthalimide 
• 89-40-7 4-nitrophthalimide 
• 99-51-4 4-nitro-o-xylene 
• 99-96-7 4-hydroxy-benzoic acid 
• 610-27-5 4-nitrophthalic acid 
• 24564-72-5 4-nitrophthalic acid chloride 

Downstream Products

• 56765-79-8 3,4-dicyanoaniline 
• 17615-42-8 1-pyrrolidino-4-nitro-2-cyanobenzene 
• 123647-06-3 1-pyrrolidino-2,3,5-tricyanobenzene 
• 123647-05-2 1-pyrrolidino-2,4,5-tricyanobenzene 
• 79319-35-0 4-piperidinophthalonitrile 
• 130028-42-1 4-([1,3]Dioxolan-4-ylmethoxy)-phthalonitrile 
• 93485-73-5 4-(pyridin-3-yloxy)phthalonitrile 
• 130028-43-2 4-(2,2-Diethyl-[1,3]dioxolan-4-ylmethoxy)-phthalonitrile 
• 83577-72-4 4-[6-(tetrahydro-pyran-2-yloxy)hexyloxy]phthalonitrile 
• 80323-72-4 4-methoxyphthalonitrile 
• 109702-53-6 4-(4-ethylphenoxy) phthalonitrile 
• 93672-98-1 1,2-dicyano-4-(neopentyloxy)benzene 
• 30757-50-7 4-hydroxy-1,2-benzenedicarbonitrile 
• 93673-02-0 1,3-bis(3',4'-dicyanophenyl)-2-ethyl-2-methylpropane 

Relevant articles and documents

Synthesis method of 4-nitrophthalonitrile

The invention discloses a synthesis method of 4-nitrophthalonitrile, which comprises the following steps: by using 4-nitrophthalonitrile, ammonia gas and air as raw materials, reacting in a fluidizedbed reactor in the presence of a catalyst to obtain 4-nitrophthalonitrile, mixing the 4-nitrophthalonitrile, ammonia gas and air in a mixer, and introducing into a reaction bed, and carrying out a contact reaction with a catalyst in a reaction bed to obtain the 4-nitrophthalonitrile. The synthesis method of the 4-nitrophthalonitrile provided by the invention is simple in process, can realize continuous reaction, is low in production cost, reduces the amount of three wastes, and can be applied to industrial production.

A 2-pyridone modified zinc phthalocyanine with three-in-one multiple functions for photodynamic therapy

A 2-pyridone modified zinc phthalocyanine (denoted ZnPc-PYR) achieves a one stone for three birds outcome in the photodynamic therapy (PDT) treatment of cancer. ZnPc-PYR can be excited by both 665 and 808 nm light to treat superficial and deep tumors, store and slowly release singlet oxygen (1O2) to improve its utilization and downregulate the HIF-1 (hypoxia-inducible factor 1) expression level to enhance the tumor cell's sensitivity to PDT treatment under hypoxic conditions.

Palladium(II) phthalocyanines efficiently promote phosphine-free Sonogashira cross-coupling reaction at room temperature

Herein we report that exceptionally simple and inexpensive Pd(II) complexes of phthalocyanines efficiently catalyze direct formation of diphenylacetylenes at ambient conditions with low loading of catalyst (0.5 mol%). Results of this study demonstrate that terminal alkynes reacted mildly with p-substituted aryl bromides at room temperature under Pd and Cu-cocatalysis to give the corresponding phenylacetylenes in yields up to 98%. Also we have examined this catalyst in Sonogashira cross-coupling with aryl chlorides and it was very effective and this reaction at room temperature that there is no examples in recent articles. This protocol represents the first use of palladium phthalocyanine as homogeneous catalyst in the Pd/Cu-promoted Sonogashira reaction. The palladium(II) phthalocyanine complex is significantly more active in Sonogashira cross-coupling between aryl halides and terminal alkynes as compared with traditional catalysts because of absence of palladium black formation through agglomeration of metal particles and deactivation of catalyst.

Preparation of new biologically active and water soluble dyes: Characterization, aggregation and extraction of metal ions from solutions

The synthesis of metallo-phthalocyanines complexes (M = Co, Ni, Cu, Zn) containing azo dye were described in this study. The metallophthalocyanines have been supported by elemental analysis, UV-visible, FT-IR and NMR. The aggregation of phthalocyanine compounds was investigated in different solvents and concentrations. The newly synthesized metallophthalocyanines possess modest antibacterial activity against various Gram-positive and Gram-negative bacteria. Moreover, these complexes have been tested as antioxidant and presented remarkable activities by two different in vitro chemical assays. They were able to reduce DPPH % radical with IC50 values ranging from 3.8 to 7.5 μmol L-1 and some of them also reduced ABTS % radical cation.

New anthracene-based-phtalocyanine semi-conducting materials: Synthesis and optoelectronic properties

A new anthracene-based semi-conducting phtalocyanines AnPc and AnPc-Tr were synthesized in solvent-free conditions. The supramolecular structure of these compounds was confirmed by NMR and FT-IR spectroscopies. Their optical properties were investigated by UV-vis and photoluminescence spectroscopies. The optical gaps were estimated from the absorption-onsets films, and the obtained values were of 1.50 eV and 1.47 eV for AnPc-Tr and AnPc respectively. In solid state, a weaker π-π-interactions of conjugated systems were obtained in the case of AnPc-Tr in comparison with AnPc. This behavior was explained by steric hindrance of triazol groups, which decrease the planarity of macromolecular structure. The HOMO and LUMO levels were estimated using cyclic voltammetry analysis; two phtalocyanine derivatives show a comparable ionization potential. The phtalacyanine containing triazole groups (AnPc-Tr) reveals a higher electron affinity in comparison with AnPc. Single-layer diode devices were fabricated and showed relatively low turn-on voltages.

Novel aqueous soluble cobalt(II) phthalocyanines of tetracarboxyl-substituted: Synthesis and catalytic activity on oxidation of sodium diethyldithiocarbamate

Enhancement of the catalytic activity of phthalocyanine catalysts by immobilizing them on polymer matrix has been studied. It has been found that the immobilization of cobalt(II) phthalocyanines on polymers enhances their catalytic activity in the oxidation of sodium diethyldithiocarbamate by air oxygen under mild conditions.

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.

UV-visible spectral study on the stability of lead phthalocyanine complexes

UV-visible electronic spectral study has been done on lead phthalocyanine (PbPc), lead tetranitro phthalocyanine (PbTNP) and lead tetraamino phthalocyanine (PbTAP) in dimethyl sulphoxide (DMSO) and H2SO4 media. Metal free phthalocyanine (H2Pc) is insoluble in DMSO and soluble in conc. H2SO4. The study has been extended to H2Pc to compare the stability of phthalocyanine structure with the PbPc complexes in H2SO4 medium. PbPc complexes are stable in DMSO, and all the complexes are more stable in 36 N H2SO4 than in 30 N and 28 N H2SO4 media. Further, complete demetallation and degradation of the phthalocyanine structure have been observed for all the PbPc complexes in 36 N H2SO4 medium within a week's time. The stability of these complexes is compared with H2Pc in H2SO4 medium. The decomposition reactions in H2SO4 media for H2Pc, PbPc, PbTNP and PbTAP are followed spectrophotometrically and rate constants were calculated. The decomposition reactions were found to follow the first-order kinetics with respect to the concentration of their respective phthalocyanine derivatives.

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 and properties of new binuclear nickel(II) phthalocyanines

New binuclear nickel(II) phthalonitrile complexes, viz., NiII 2,2′,9(10),9′(10′),17(18),17′(18′),24(25), 24′(25′)-tetra(phenylene-1,2-dioxy)bisphthalocyanine and Ni II 2,2′,9(10),9′(10′),17(18),17′(18′), 24(25),24′(25′)-tetra(4-tert-butyl-phenylene-1,2-dioxy) bisphthalocyanine, were synthesized. The complexes were characterized by electronic spectroscopy and MALDI-TOF mass spectrometry and studied as active components for membranes of ion-selective electrodes in solutions of dicarboxylic acids.