391980

Sigma-Aldrich

1,2,4,5-Tetracyanobenzene

97%

Synonym(s):
Pyromellitic acid tetranitrile, 1,2,4,5-Benzenetetracarbonitrile
Linear Formula:
C6H2(CN)4
CAS Number:
Molecular Weight:
178.15
Beilstein/REAXYS Number:
1875027
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

97%

mp

265-268 °C (lit.)

solubility

acetone: soluble 25 mg/mL, clear, colorless to yellow

SMILES string

N#Cc1cc(C#N)c(cc1C#N)C#N

InChI

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

InChI key

FAAXSAZENACQBT-UHFFFAOYSA-N

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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.

Application

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).

Packaging

1, 5 g in glass bottle

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

23/24/25

Safety Statement

36/37/39-45

RIDADR

UN 3439 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Fuyuki Ito et al.
Journal of the American Chemical Society, 125(16), 4722-4723 (2003-04-17)
Magnetic field effects on the charge-transfer (CT) fluorescence of a 1,2,4,5-tetracyanobenzene-doped poly(N-vinylcarbazole) thin film were investigated to clarify the primary process in photoconductive organic amorphous solid. The CT fluorescence increased with increasing magnetic field until 10 mT, and then it...
Formation of cocrystal nanorods by solid-state reaction of tetracyanobenzene in 9-methylanthracene molecular crystal nanorods.
Al-Kaysi RO, et al.
Crystal Growth & Design, 9(4), 1780-1785 (2009)
Hydrothermal Synthesis of a 3D Polymeric Cobalt (II) Carboxylate Derivative from 1, 2, 4, 5-Benzenetetracarbonitrile.
Sun B, et al.
Zeitschrift fur Anorganische und Allgemeine Chemie, 635(15), 2375-2377 (2009)
Structural Studies of the 1: 1 Complex of o-3, 4-Dimethyltetrathiafulvalene (o-Me2TTF) and 1, 2, 4, 5-Tetracyanobenzene (TCNB).
Reinheimer EW, et al.
Journal of Chemical Crystallography, 40(6), 514-519 (2010)
Xin Ye et al.
Nature communications, 10(1), 761-761 (2019-02-17)
Organic cocrystals possess valuable properties owing to the synergistic effect of the individual components. However, the growth of molecular cocrystals is still in its primary stage. Here we develop a microspacing in-air sublimation method to grow organic cocrystals, and furthermore...

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