1,2,4,5-Tetracyanobenzene

Base Information

• Chemical Name: 1,2,4,5-Tetracyanobenzene
• CAS No.: 712-74-3
• Molecular Formula: C10H2N4
• Molecular Weight: 178.153
• Hs Code.: 29269090
• European Community (EC) Number: 627-771-1
• DSSTox Substance ID: DTXSID00221399
• Nikkaji Number: J54.508B
• Wikidata: Q72445127
• Mol file: 712-74-3.mol

Synonyms:1,2,4,5-tetracyanobenzene;p-dicyanobenzene;tetracyanobenzene

Chemical Property of 1,2,4,5-Tetracyanobenzene

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 3.74E-08mmHg at 25°C
• Melting Point: 265-268 °C(lit.)
• Refractive Index: 1.61
• Boiling Point: 446.1 °C at 760 mmHg
• Flash Point: 235.3 °C
• PSA: 95.16000
• Density: 1.37 g/cm³
• LogP: 1.17332
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: acetone: soluble25mg/mL, clear, colorless to yellow
• Water Solubility.: Soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 178.027946081
• Heavy Atom Count: 14
• Complexity: 332

Purity/Quality:

97% ^*data from raw suppliers

Benzene-1,2,4,5-tetracarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C(=CC(=C1C#N)C#N)C#N)C#N
• Uses: 1,2,4,5-Tetracyanobenzene (TCB, TCNB) is suitable reagent used in the synthesis of o-3,4-dimethyltetrathiafulvalene (o-Me2TTF)-1,2,4,5-tetracyanobenzene (TCNB) 1:1 complex and radiative exciplexes of TCB in non-polar solvents.1,2,4,5-Tetracyanobenzene (Pyromellitic acid tetranitrile, PMTN, TCB, TCNB, 1,2,4,5-benzenetetracarbonitrile ) may be used in the following studies:Solid-state diffusion of TCNB into 9-methylanthracene molecular crystal nanorods forming cocrystal nanorods.Synthesis of copper polyphthalocyanine (CuPPC) thin films, an elementoorganic semiconductor.Preparation of charge transfer (CT) nanocrystallites which may have a potential use in nanofluidics to observe the rotational motion of nanoobjects.Hydrothermal synthesis of Co2(terpy)2(btec)?H2O (terpy = 2,2′:6′,2"-terpyridine, btec = 1,2,4,5-benzenetetracarboxylate).

Technology Process of 1,2,4,5-Tetracyanobenzene

There total 15 articles about 1,2,4,5-Tetracyanobenzene 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:

Reference yield: 73.0%

zinc(II) cyanide (557-21-1) + 4,5-dibromobenzene-1,2-dicarbonitrile (86938-64-9) → 1,2,4,5-tetracyanobenzene (712-74-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; polymethylhydroxysilane; In N,N-dimethyl acetamide; at 100 ℃; for 4h;

DOI:10.1055/s-2008-1078269

Reference yield: 72.0%

1,2,4,5-Benzenetetracarboxylic acid tetraamide (6183-35-3) → 1,2,4,5-tetracyanobenzene (712-74-3)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

Reference yield: 72.0%

zinc(II) cyanide (557-21-1) + 1,2,4,5-tetrabromobenzene (636-28-2) → 1,2,4,5-tetracyanobenzene (712-74-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; polymethylhydroxysilane; In N,N-dimethyl acetamide; at 100 ℃; for 8h;

DOI:10.1055/s-2008-1078269

upstream raw materials:

1,2,4,5-Benzenetetracarboxylic acid tetraamide

Pyromellitic dianhydride

pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone

1,2,4,5-benzenetetracarboxylic acid

Downstream raw materials:

2-cyano-1,4-benzenedicarbonitrile

2,4,5-tricyanoaniline

5-(1-Methyl-pyrrolidin-2-yl)-benzene-1,2,4-tricarbonitrile

5-Methyl-1,2,4-benzenetricarbonitrile

Refernces

Phenyl-substituted planar binuclear phthalo- and naphthalocyanines: Synthesis and investigation of physicochemical properties

10.1016/j.dyepig.2011.10.012

The study explores the synthesis and properties of phenyl-substituted planar binuclear phthalocyanine and naphthalocyanine magnesium complexes with extended π-conjugation systems. The researchers synthesized these compounds using various chemical reactions, including Suzuki-Miyaura cross-coupling and condensation reactions. Key chemicals involved include pyromellitonitrile, 2,3,6,7-tetracyanonaphthaline, 1,2-dicyano-4,5-diphenylbenzene, and 6,7-diphenylnaphthalene-2,3-dicarbonitrile, which served as starting materials or intermediates. Magnesium acetate was used as a metal source, and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) was employed as a base to facilitate the formation of the binuclear complexes. The synthesized compounds were characterized using techniques such as MALDI-TOF mass spectrometry, UV/Vis/NIR spectroscopy, and 1H NMR spectroscopy. The study investigates the correlation between the extension of the aromatic system and the position of absorption in the near-IR region, as well as the electrochemical properties of these binuclear complexes. The results show that extending the π-system leads to significant red-shifts in absorption maxima, with the Q2-band of a binuclear naphthalocyanine complex reaching up to 972 nm. The study also examines the aggregation behavior of these compounds in different solvents and their redox properties using cyclic voltammetry and square-wave voltammetry.