712-74-3

Basic information

• Product Name: benzene-1,2,4,5-tetracarbonitrile
• Synonyms: 1,2,4,5-Benzenetetranitrile;1,2,4,5-Benzentetrakarbonitril;Benzene, 1,2,4,5-tetracyano-;Pyromellitic nitrile;Pyromellitic tetranitrile;pyromelliticnitrile;pyromellitictetranitrile;Pyromellitotetranitrile
• CAS NO: 712-74-3
• Molecular Formula: C₁₀H₂N₄
• Molecular Weight: 178.15
• Product Categories: Aromatic Nitriles;Functional Materials;Phthalonitriles & Naphthalonitriles;Phthalonitriles (Building Blocks for Phthalocyanines);Building Blocks;C10 to C27;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 712-74-3.mol

Chemical Properties

• Melting Point: 265-268 °C(lit.)
• Boiling Point: 300.36°C (rough estimate)
• Flash Point: 235.3 °C
• Appearance: white crystalline solid
• Density: 1.35 g/cm3
• Vapor Pressure: 3.74E-08mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: acetone: soluble25mg/mL, clear, colorless to yellow
• Water Solubility: Soluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 1875027
• CAS DataBase Reference: benzene-1,2,4,5-tetracarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: benzene-1,2,4,5-tetracarbonitrile(712-74-3)
• EPA Substance Registry System: benzene-1,2,4,5-tetracarbonitrile(712-74-3)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: UN 3439 6.1/PG 2
• WGK Germany: 3
• RTECS: DB9100000
• TSCA: N
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 712-74-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1,2,4,5-Tetracyanobenzene is used as a suitable reagent for 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. This application is crucial for the development of new compounds and materials with potential applications in various industries.
Used in Solid-state Diffusion Studies:
In the field of materials science, 1,2,4,5-tetracyanobenzene is used for solid-state diffusion into 9-methylanthracene molecular crystal nanorods, forming cocrystal nanorods. This process is essential for understanding the behavior of molecules in solid-state environments and their potential applications in nanotechnology.
Used in Thin Film Synthesis:
1,2,4,5-Tetracyanobenzene is utilized in the synthesis of copper polyphthalocyanine (CuPPC) thin films, an elementoorganic semiconductor. These thin films have potential applications in electronic devices, sensors, and other advanced technologies.
Used in Charge Transfer Nanocrystallite Preparation:
1,2,4,5-TETRACYANOBENZENE is used in the preparation of charge transfer (CT) nanocrystallites, which may have potential use in nanofluidics to observe the rotational motion of nanoobjects. This application contributes to the advancement of nanotechnology and the development of new materials with unique properties.
Used in Hydrothermal Synthesis:
1,2,4,5-Tetracyanobenzene is employed in the hydrothermal synthesis of Co2(terpy)2(btec)?H2O (terpy = 2,2′:6′,2"-terpyridine, btec = 1,2,4,5-benzenetetracarboxylate). This process is vital for the creation of new compounds with potential applications in various fields, including pharmaceuticals, materials science, and electronics.

Synthesis Reference(s)

The Journal of Organic Chemistry, 27, p. 3520, 1962 DOI: 10.1021/jo01057a028

Purification Methods

Crystallise the tetra-nitrile from EtOH and sublime in vacuo. [Lawton & McRitchie J Org Chem 24 26 1959, Bailey et al. Tetrahedron 19 161 1963, Beilstein 9 IV 3800.]

InChI:InChI=1/C10H2N4/c11-3-7-1-8(4-12)10(6-14)2-9(7)5-13/h1-2H

Upstream product

• 6183-35-3 1,2,4,5-Benzenetetracarboxylic acid tetraamide 
• 281-23-2 adamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 20440-81-7 1-tert-butyladamantane 
• 23074-42-2 1-adamantanecarbonitrile 
• 21898-97-5 adamantan-1-ylmethyl methyl ether 
• 770-71-8 1-adamantanemethanol 
• 6221-74-5 1-methoxyadamantane 
• 557-21-1 zinc(II) cyanide 
• 86938-64-9 4,5-dibromobenzene-1,2-dicarbonitrile 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 89-05-4 1,2,4,5-benzenetetracarboxylic acid 
• 2550-73-4 pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 89-32-7 Pyromellitic dianhydride 

Downstream Products

• 10347-14-5 2-cyano-1,4-benzenedicarbonitrile 
• 105465-33-6 2,4,5-tricyanoaniline 
• 105465-34-7 5-(1-Methyl-pyrrolidin-2-yl)-benzene-1,2,4-tricarbonitrile 
• 139071-46-8 2-(2,4,5-Tricyanophenyl)-1,3-dioxolane 
• 19798-71-1 2-methyl-2-methoxy-1,3-dioxolane 
• 132381-82-9 5-tert-Butyl-1,2,4-Benzenetricarbonitrile 
• 542-59-6 2-hydroxyethyl acetate 
• 97419-14-2 2-(2,2,2-trifluoroethoxy)-2-methyl-1,3-dioxolane 
• 139071-39-9 5-Hexyl-1,2,4-benzenetricarbonitrile 
• 464-07-3 3,3-dimethyl-2-butanol 
• 139071-40-2 1,4-dicyano-2,5-bis(1,1-dimethylethyl)benzene 
• 139100-52-0 2,4-dicyano-1,5-bis(1,1-dimethylethyl)benzene 
• 16179-36-5 2-Hydroxyethyl pentanoate 
• 106-73-0 methyl heptanoate 

Relevant articles and documents

Observation of a Symmetry-Forbidden Excited Quadrupole-Bound State

We report the observation of a symmetry-forbidden excited quadrupole-bound state (QBS) in the tetracyanobenzene anion (TCNB-) using both photoelectron and photodetachment spectroscopies of cryogenically-cooled anions. The electron affinity of TCNB is accu

Corresponding amine nitrile and method of manufacturing thereof

The present invention relates to a nitrile manufacturing method, which has characteristics of significantly-reduced ammonia source consumption, low environmental pressure, low energy consumption, low production cost, high nitrile purity, high nitrile yield and the like compared with the method in the prior art, wherein nitrile having a complicated structure can be obtained through the method. The present invention further relates to a method for producing a corresponding amine from the nitrile.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a preparation method of nitrile. Compared with the prior art, the preparation method has the characteristics of obvious reduction of the usage amount of ammonia sources, low environmental pressure, low energy consumption, low production cost, high purity and yields of nitrile products, and the like, and can be used for obtaining nitrile with a more complex structure. The invention also relates to a method for preparing corresponding amine with nitrile.

Corresponding amine nitrile and method of manufacturing thereof (by machine translation)

The invention relates to a method of manufacturing one kind of nitrile, compared with the prior art, has significantly reduced the amount of ammonia, the environmental pressure of the small, low energy consumption, low production cost, nitrile product purity and yield and the like, and can obtain more complex structure of the nitriles. The invention also relates to the corresponding amine by the nitrile manufacture method. (by machine translation)

Synthesis of phthalonitriles using a palladium catalyst

An easy synthetic method to obtain phthalonitriles from o-dibromobenzenes under mild conditions in high yields using Zn(CN)2 and a catalytic amount of tris(dibenzylideneacetone)dipalladium and 1,1′- bis(diphenylphosphino)ferrocene is described. Georg Thieme Verlag Stuttgart.

Oxidative functionalization of adamantane and some of its derivatives in solution

1,2,4,5-Benzenetetracarbonitrile (TCB) is irradiated in the presence of adamantane (1) and some of its derivatives. The singlet excited state of TCB is a strong oxidant, and there is various evidence, including time-resolved spectroscopy, to prove that SET from the alkane to TCB1* takes place and yields the corresponding radical ions. The adamantane radical cation deprotonates from the bridgehead position, and the resulting radical couples with TCB-*. Deprotonation via the radical cation occurs with a number of substituted adamantanes and remains the exclusive or predominating reaction also with derivatives containing a potential electrofugal group, such as one of the following carbocations: t-Bu, CH2OMe, CH2OH (notable here is that C-H deprotonation is more efficient than O-H deprotonation). A carboxy group is lost more efficiently than a proton, however. In contrast, detaching of such cations is the main process when the radical cations of substituted adamantanes is produced anodically. This different behavior is explained on the basis of thermochemical calculation and of the different environments experienced by the radical cation in the two cases, viz reaction from the solvated radical cation in the first case and from the substrate adsorbed on the anode in the latter one. 1-Methoxyadamantane deprotonates from the methyl group, a reaction explained by the different structure of the radical cation. On the other hand, the radical NO3*, conveniently produced by photolysis of cerium(IV) ammonium nitrate, reacts by hydrogen abstraction with selective attack at the bridgehead position and little interference by substituents and thus offers a useful way for the selective oxidative functionalization of adamantanes.

Electron Transfer Photoinduced Cleavage of Acetals. A Mild Preparation of Alkyl Radicals

Electron transfer from 2-alkyl- and 2,2-dialkyldioxolanes as well as from open-chain ketals to singlet excited benzene-1,2,4,5-tetracarbonitrile (TCNB) is followed by fragmentation of the donors radical cation to yield alkyl radicals and dialkoxy carbocations.The first species are trapped by TCNB to yield alkylbenzenetricarbonitriles (substitution of a second cyano group can be obtained sequentially) and in a minor path are reduced to alkanes, while the latter ones react with nucleophiles to give ortho acid derivatives.In view of the results of radical clock experiments, it is assumed that part of the process is a concerted (radical cation cleavage-addition to the aromatic) reaction, while another part involves the free-radical cation.On the other hand, intersystem crossing from the singlet radical ion pair to the triplet manifold causes cleavage of the acetal to the corresponding carbonyl derivative.This reaction offers a mild method for the preparation of alkyl radicals via C-C bonds cleavage.

Octaalkyl Esters of 2,3,9,10,16,17,23,24-(29H,31H)-Phthalocyanineoctacarboxylic Acid: A New Homologous Series of Discotis Liquid Crystals

The synthesis of a homologous series of octaalkoxycarbonyl-substitued metal-free phthalocyanines (Pc) is described.The mesomorphic properties of these new materials were studied by differential scanning calorimetry (DSC), optical microscopy and X-ray investigations.All compounds show a discotic mesophase in an extremely large temperature interval including room temperature.X-ray diffraction patterns of the mesophases confirm that all compounds form a hexagonal columnar mesophase of the type Dho.