712-74-3

Basic information

• Product Name: 1,2,4,5-TETRACYANOBENZENE
• 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
• Article Data: 8

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: 1,2,4,5-TETRACYANOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4,5-TETRACYANOBENZENE(712-74-3)
• EPA Substance Registry System: 1,2,4,5-TETRACYANOBENZENE(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

Chemical Properties

solid

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).

Synthesis Reference(s)

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

General Description

1,2,4,5-Tetracyanobenzene (TCNB, TCB) is a tetra substituted benzene. The IR and raman spectra of TCNB and its 1:1 complex with durene has been recorded. The time-resolved linear dichroism spectroscopic study of hexamethylbenzene-1,2,4,5-tetracyanobenzene charge-transfer complex has been investigated. The influence of magnetic field on the charge-transfer fluorescence of 1,2,4,5-tetracyanobenzene-doped poly(N-vinylcarbazole) thin film has been studied.

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 
• 557-21-1 zinc(II) cyanide 
• 636-28-2 1,2,4,5-tetrabromobenzene 
• 86938-64-9 4,5-dibromobenzene-1,2-dicarbonitrile 
• 21898-97-5 adamantan-1-ylmethyl methyl ether 
• 23074-42-2 1-adamantanecarbonitrile 
• 20440-81-7 1-tert-butyladamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 281-23-2 adamantane 
• 770-71-8 1-adamantanemethanol 
• 6221-74-5 1-methoxyadamantane 
• 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

• 110-54-3 hexane 
• 542-59-6 2-hydroxyethyl acetate 
• 139071-39-9 5-Hexyl-1,2,4-benzenetricarbonitrile 
• 88830-21-1 5-isopropylbenzene-1,2,4-tricarbonitrile 
• 10347-14-5 2-cyano-1,4-benzenedicarbonitrile 
• 88830-20-0 5-Methyl-1,2,4-benzenetricarbonitrile 
• 7677-24-9 trimethylsilyl cyanide 
• 132381-81-8 5-butylbenzene-1,2,4-tricarbonitrile 
• 935-67-1 Cumyl methyl ether 
• 110596-37-7 5-(2,4,6-trimethylbenzyl)-1,2,4-benzenetricarbonitrile 
• 110596-39-9 5-(3,4,5-trimethylbenzyl)-1,2,4-benzenetricarbonitrile 
• 110596-38-8 5-(2,3,5-trimethylbenzyl)-1,2,4-benzenetricarbonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 90-96-0 bis(p-methoxyphenyl)methanone 

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 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.

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.