56765-79-8

Basic information

• Product Name: 4-Aminophthalonitrile
• Synonyms: 3,4-DICYANOANILINE;4-AMINOPHTHALONITRILE;4-AMINO-1,2-BENZENEDICARBONITRILE;4-amino-2-benzenedicarbonitrile;3,4-Dicyanoanline;4-AMINOPHTALONITRILE;1,2-Benzenedicarbonitrile, 4-amino-;3,4-Dicyanoaniline4-amino-1,2-benzenedicarbonitrile
• CAS NO: 56765-79-8
• Molecular Formula: C₈H₅N₃
• Molecular Weight: 143.15
• EINECS: 260-370-6
• Product Categories: Aromatic Nitriles;Phthalonitriles & Naphthalonitriles;Phthalonitriles (Building Blocks for Phthalocyanines);Functional Materials
• Mol File: 56765-79-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 179-181 °C(lit.)
• Boiling Point: 251.23°C (rough estimate)
• Flash Point: 204.7 °C
• Appearance: Orange/Crystalline Powder
• Density: 1.2597 (rough estimate)
• Vapor Pressure: 4.34E-07mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: -0.09±0.10(Predicted)
• Water Solubility: Insoluble
• BRN: 2937382
• CAS DataBase Reference: 4-Aminophthalonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aminophthalonitrile(56765-79-8)
• EPA Substance Registry System: 4-Aminophthalonitrile(56765-79-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 24/25-36/37/38-25-24
• Safety Statements: 45-36/37-28A-22-36-26
• RIDADR: 3439
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 56765-79-8(Hazardous Substances Data)

Usage

Chemical Properties

orange crystalline powder

Flammability and Explosibility

Notclassified

Synthesis

45 mL of methanol and 9.6 mL of concentrated HCl were stirred in a round-bottomed flask. 2.02 g (145 mmol) of 4-nitrophthalonitrile was added into this medium. The mixture was heated to reflux. 4-Nitrophthalonitrile dissolved in this step. Iron powder (2.21 g, 39.2 mmol) was added in portions within an hour. The color of solution changed to yellow-brown. After the addition of iron has been completed, the reaction medium was continued to stir at reflux temperature for another hour. The reaction medium was cooled to room temperature. It was precipitated with 60 mL of water. The precipitate was filtered and washed with copious amount of water. Molecular formula: H2NC6H3-1,2-(CN)2. Yield: 1.4 g (81.59%).

InChI:InChI=1/C8H5N3/c9-4-6-1-2-8(11)3-7(6)5-10/h1-3H,11H2

Upstream product

• 31643-49-9 4-Nitrophthalonitrile 
• 89-40-7 4-nitrophthalimide 
• 136918-14-4 phthalimide 
• 557-21-1 zinc(II) cyanide 
• 615-55-4 3,4-dibromoaniline 
• 1033995-63-9 oxonium 
• 24564-72-5 4-nitrophthalic acid chloride 
• 13138-53-9 4-nitrophthalic amide 
• 610-27-5 4-nitrophthalic acid 

Downstream Products

• 125103-70-0 N-(3,4-Dicyano-phenyl)-4-(4-methoxy-phenyl)-2,4-dioxo-butyramide 
• 125103-69-7 N-(3,4-Dicyano-phenyl)-2,4-dioxo-4-p-tolyl-butyramide 
• 170697-25-3 3,4-dicyanobenzenesulfonyl chloride 
• 170697-23-1 3,4-dicyanobenzenesulfonic acid 
• 1141444-52-1 4-(2-cyclohexyl-1H-imidazo[4,5-c]quinolin-4-ylamino)phthalonitrile 
• 170697-26-4 (3,4-dicyano)phenyldiazonium chloride 
• 1237531-87-1 3-(3',4'-dicyanophenylazo)-2-hydroxy-9-carbazole 

Relevant articles and documents

Azo-coupled zinc phthalocyanines: Towards broad absorption and application in dye-sensitized solar cells

The synthesis of symmetrical azo-coupled zinc phthalocyanines (7, 8, 10 and 11) incorporating two spectrally complementary photogenerators (azo dyes and phthalocyanines) by NN double bonds in a single structure was described. The four sensitizers were fully characterized by Fourier Transform infrared spectroscopy, UV-Vis spectroscopy, proton nuclear magnetic resonance, mass spectrometry, elemental analyses, thermogravimetric analysis and cyclic voltammetry. All the azo-coupled phthalocyanines exhibited broad absorptions covering the range 300-800 nm. The cyclic voltammetry studies indicated that the LUMO and HOMO energy levels of four synthesized azo-coupled phthalocyanines could ensure efficient electron injection and thermodynamically favorable dye regeneration. Thermal stability studies showed that the four sensitizers were stable above 200 °C. The new compounds were tested in dye-sensitized solar cells and compound 8 showed the best photovoltaic performance, yielding 2.7% power conversion efficiency.

The new ball-type zinc phthalocyanine with S[sbnd]S bridge; Synthesis, computational and photophysicochemical properties

In this study, the starting compound 4,4′-disulfanediyldiphthalonitrile (1) and its ball-type zinc phthalocyanine (2) were synthesized and characterized by standard spectroscopic methods. The molecular structure and supramolecular dynamics of the compound (1) have been investigated by the analysis of the single crystal X-ray diffraction data. To further understand the intermolecular interactions of compound (1), the Hirshfeld surface analysis has been carried out. The compound (1) and (2) were investigated by quantum chemical calculations. Their quantum chemical parameters such as highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), chemical hardness were performed by B3lyp, HF, M062x method. The ΔG values of the compound (1) and (2) were calculated by using the obtained results. The calculated Infrared spectroscopy, Nuclear Magnetic Resonance, and UV–vis spectra of the compounds were investigated. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized ball-type zinc phthalocyanine (2) were investigated in dimethyl sulfoxide (DMSO) solutions. We obtained very high singlet oxygen quantum yields as 0.89, suggesting its potential as photosensitizer in PDT treatment.

Axial and peripheral tetraarylethylene-modified subphthalocyanines with distinctive fluorescent performances

Special aromatic structure and unique geometric characteristics make subphthalocyanines possess distinctive electronic structures and physicochemical properties. In this paper, tetraarylethylenes with aggregation-induced emission were introduced to subphthalocyanine macrocycles at the axial direction and the periphery to improve the fluorescence emission properties. Results show that the modification at the two different positions of the subphthalocyanines has different effects on regulating the fluorescence performances. The subphthalocyanine modified axially by tetraphenylethylene shows outstanding fluorescence resonance energy transfer (FRET) phenomenon, and the modification on the periphery of subphthalocyanine is conducive to enhance the fluorescence intensity. These distinctive performances have the potential applications in fluorescence sensor and probe.

Preparation method of diamine containing phthalonitrile group

The invention relates to a preparation method of a diamine containing phthalonitrile group. , 4 - Aminophthalonitrile is prepared from 4 -nitrophthalonitrile by reducing the nitro group, then a phthalonitrile group-containing dinitro compound is prepared by reaction of benzoquinone containing phthalonitrile group, and the dinitro compound containing phthalonitrile group is obtained through reaction of the dihydric phenol with 4 - 4 -nitrofluorobenzene. The method can be used for preparing binary amines containing phthalonitrile groups on a scale. The product is single. When the overall conversion rate reaches 50% or more, a phthalonitrile group-containing diamine having a high purity 90% or more can be obtained. The method is simple in production operation and low in equipment requirement.

Subphthalocyanines as Efficient Photosensitizers with Nanomolar Photodynamic Activity against Cancer Cells

Because cancer is the second leading cause of death globally, investigation of new photosensitizers for photodynamic therapy is highly desirable. In this work, different peripherally substituted subphthalocyanines (SubPcs) with either a benzocrown moiety (CE-) or a tyrosine methyl ester (Tyr-) as the axial ligand have been prepared. Target SubPcs showed high φΔ values, >0.50 in EtOH. Both CE- and Tyr- moieties increased substantially the hydrophilicity of the compounds (log P = 1.79-2.63, n-octanol/PBS). Uptake to cells, subcellular localization, and monitoring of the progression of cell death over time are described. Improved spectroscopic behavior of the CE- series in cell culture medium resulted in higher photodynamic activity versus that of the Tyr- series. In particular, the peripherally triethylsulfanyl SubPc-CE exhibited extraordinarily low EC50 values of 2.3 and 4.4 nM after light activation and high TC50 values of 14.49 and 5.25 μM (i.e., dark toxicity without activation) on SK-MEL-28 and HeLa cells, respectively, which rank it among the best photosensitizers ever.