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Phthalonitrile

Base Information
  • Chemical Name:Phthalonitrile
  • CAS No.:91-15-6
  • Molecular Formula:C8H4N2
  • Molecular Weight:128.133
  • Hs Code.:29269095
  • European Community (EC) Number:202-044-8
  • ICSC Number:0670
  • NSC Number:17562
  • UN Number:3276
  • UNII:978627YAJU
  • DSSTox Substance ID:DTXSID8029604
  • Nikkaji Number:J3.921G
  • Wikipedia:Phthalonitrile
  • Wikidata:Q408783
  • ChEMBL ID:CHEMBL3185350
  • Mol file:91-15-6.mol
Phthalonitrile

Synonyms:1,2-benzenedicarbonitrile;1,2-dicyanobenzene;o-phthalodinitrile

Suppliers and Price of Phthalonitrile
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • 1,2-Dicyanobenzene
  • 10g
  • $ 305.00
  • TRC
  • 1,2-Dicyanobenzene
  • 25g
  • $ 55.00
  • TRC
  • 1,2-Dicyanobenzene
  • 50g
  • $ 70.00
  • TCI Chemical
  • Phthalonitrile >99.0%(GC)
  • 500g
  • $ 112.00
  • TCI Chemical
  • Phthalonitrile >99.0%(GC)
  • 25g
  • $ 14.00
  • TCI Chemical
  • Phthalonitrile >99.0%(GC)
  • 100g
  • $ 25.00
  • Sigma-Aldrich
  • Phthalonitrile for synthesis. CAS 91-15-6, EC Number 202-044-8, chemical formula C H -1,2-(CN) ., for synthesis
  • 8005930100
  • $ 28.90
  • Sigma-Aldrich
  • Phthalonitrile for synthesis
  • 100 g
  • $ 27.66
  • Sigma-Aldrich
  • 1,2-Dicyanobenzene 98%
  • 100g
  • $ 23.90
  • Sigma-Aldrich
  • 1,2-Dicyanobenzene 98%
  • 500g
  • $ 81.00
Total 114 raw suppliers
Chemical Property of Phthalonitrile
Chemical Property:
  • Appearance/Colour:off-white to tan powder 
  • Vapor Pressure:0.000865mmHg at 25°C 
  • Melting Point:137-139 °C(lit.) 
  • Refractive Index:1.565 
  • Boiling Point:304.6 °C at 760 mmHg 
  • Flash Point:153.3 °C 
  • PSA:47.58000 
  • Density:1.24 g/cm3 
  • LogP:1.42996 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:benzene: 50 mg/mL, clear 
  • Water Solubility.:0.56 g/L (25 ºC) 
  • XLogP3:1
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:128.037448136
  • Heavy Atom Count:10
  • Complexity:178
Purity/Quality:

99.9% *data from raw suppliers

1,2-Dicyanobenzene *data from reagent suppliers

Safty Information:
  • Pictogram(s): Toxic
  • Hazard Codes:
  • Statements: 25-23/24/25 
  • Safety Statements: 36/37/39-45-28A 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Nitrogen Compounds -> Nitriles
  • Canonical SMILES:C1=CC=C(C(=C1)C#N)C#N
  • Inhalation Risk:A harmful concentration of airborne particles can be reached quickly when dispersed.
  • Effects of Short Term Exposure:The substance may cause effects on the central nervous system.
  • General Description Phthalonitrile, also known by various names such as 1,2-dicyanobenzene or o-benzenedinitrile, is a key precursor in the synthesis of phthalocyanines and related compounds, which are widely used in optoelectronic applications due to their unique optical and electronic properties. It serves as a versatile building block in organic synthesis, enabling the formation of complex structures like subphthalocyanine dimers and metal complexes with catalytic activity. Phthalonitrile's reactivity allows for modifications under mild conditions, as demonstrated by palladium-catalyzed cyanation methods, which offer high yields and functional group tolerance. Its derivatives, such as oxadiazolines and palladium complexes, further highlight its utility in cross-coupling reactions and materials science.
Technology Process of Phthalonitrile

There total 102 articles about Phthalonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With potassium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 12h;
DOI:10.1016/j.tetlet.2015.12.019
Guidance literature:
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride; In 1,2-dichloro-ethane; at 20 - 50 ℃; for 16h;
DOI:10.1016/j.tetlet.2019.04.043
Guidance literature:
With palladium diacetate; sodium carbonate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In N,N-dimethyl acetamide; at 120 ℃; for 3h;
DOI:10.1055/s-0034-1379899
Refernces

Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules

10.2298/JSC150430063O

The research presents the synthesis and evaluation of new cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea-based groups for their potential as antimalarial agents against chloroquine-resistant and susceptible Plasmodium falciparum strains, and as anti-cancer molecules. The study involved the synthesis of derivatives using reactants such as gem-dihydroperoxide, benzyl 4-oxocyclohexanecarboxylate, and various coupling agents, followed by comprehensive analyses including NMR, IR, MS, and HPLC to characterize the compounds. The antimalarial activity was assessed using the Malaria SYBR Green I based fluorescence assay against different P. falciparum strains, while cytotoxicity was determined on human normal peripheral blood mononuclear cells (PBMC). Additionally, select compounds were tested for in vitro cytotoxic activity against various human cancer cell lines and in vivo activity against Toxoplasma gondii in a murine model. The experiments utilized techniques like MTT tests for cell survival, flow cytometry for cell cycle analysis, and microscopic examination for morphological assessment of cell death. The study identified derivative 24 as the most promising candidate with low nanomolar antimalarial activities, high selectivity indices, and significant in vivo potential against T. gondii.

Synthesis of phthalonitriles using a palladium catalyst

10.1055/s-2008-1078269

The research presents an innovative and efficient method for synthesizing phthalonitriles from o-dibromobenzenes under mild conditions. The purpose of this study is to develop an alternative to the traditional Rosenmund–von Braun reaction, which often suffers from low yields and harsh reaction conditions. The researchers utilized key chemicals such as Zn(CN)?, tris(dibenzylideneacetone)dipalladium (Pd?(dba)?), and 1,1′-bis(diphenylphosphino)ferrocene (DPPF) as catalysts in dimethylacetamide (DMAC) solvent. The method demonstrated high yields (between 62% and 97%) and was effective for various o-dibromobenzenes with different substituents, including electron-donating and electron-withdrawing groups. The study concluded that this palladium-catalyzed cyanation method is a significant improvement over existing methods, offering milder conditions, higher yields, and the ability to tolerate a wide range of functional groups without the formation of unwanted byproducts.

Synthesis of symmetrical and unsymmetrical subphthalocyanine dimers containing a hydroquinone bridge

10.1142/S1088424613500909

This study focuses on the synthesis and characterization of three novel hydroquinone-based subphthalocyanine (SubPc) dimers. The researchers used phthalonitriles and BCl? to synthesize chloro-subphthalocyanines (Cl-SubPcs), which then underwent axial substitution with hydroquinone to form hydroquinone-substituted SubPcs (Hq-SubPcs). These Hq-SubPcs acted as nucleophiles and reacted with Cl-SubPcs to create symmetrical and unsymmetrical dimers. The synthesis involved reacting hydroquinone and the respective SubPcs in a 1:1 molar ratio in toluene at 180 °C in a pressure vessel. The resulting dimers were characterized using 1H NMR, 13C NMR, UV-vis, fluorescence, and mass spectral analysis. The study highlights the potential of these dimers for applications in optoelectronic devices due to their enhanced solubility and tailored absorption properties.

Metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles: Syntheses of oxadiazolines as well as phthalamide-PdII and dihydropyrrolyl-iminoisoindolinone-Pd II complexes with high catalytic activity in suzuki-miyaura cross-coupling reactions

10.1002/chem.200800510

The research focuses on metal-free and PdII-promoted [2+3] cycloadditions of a cyclic nitrone to phthalonitriles, leading to the synthesis of oxadiazolines, phthalamide-PdII complexes, and dihydropyrrolyl-iminoisoindolinone-PdII complexes. These compounds were characterized using IR, 1H, and 13C NMR spectroscopy, ESI MS or FAB+ MS, elemental analyses, and X-ray diffraction analysis. The study also explores the high catalytic activity of these complexes in Suzuki-Miyaura cross-coupling reactions. The experiments involved heating mixtures of phthalonitriles and a cyclic nitrone in a sealed tube, and in some cases, the presence of palladium(II) chloride was used to facilitate the reaction. The reactants included various substituted phthalonitriles and a cyclic nitrone, while the analyses were employed to confirm the structures and properties of the synthesized compounds.

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