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Sigma-Aldrich

1,2,4,5-Tetracyanobenzene

97%

Synonym(s):

1,2,4,5-Benzenetetracarbonitrile, Pyromellitic acid tetranitrile

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About This Item

Linear Formula:
C6H2(CN)4
CAS Number:
712-74-3
Molecular Weight:
178.15
Beilstein:
1875027
MDL number:
MFCD00043481
UNSPSC Code:
12352100
PubChem Substance ID:
24864415
NACRES:
NA.22

Assay

97%

form

solid

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).

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300,H311 + H331

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nanosized crystallites of charge-transfer complex of 9-methylanthracene and 1, 2, 4, 5-tetracyanobenzene for bright and optically anisotropic fluorescent probes.
Hosaka N, et al.
Applied Physics Letters, 92(11), 113305-113305 (2008)
Synthesis and structure of high-quality films of copper polyphthalocyanine-2D conductive polymer.
Sedlovets DM, et al.
Materials Research Bulletin, 48(10), 3955-3960 (2013)
Radiative exciplexes of 1, 2, 4, 5-Tetracyanobenzene with sterically hindered alkylbenzenes.
Zhou J, et al.
The Journal of Physical Chemistry A, 107(40), 8319-8326 (2003)
Application of time-resolved linear dichroism spectroscopy: Relaxation of excited hexamethylbenzene/1, 2, 4, 5-tetracyanobenzene charge-transfer complexes.
Arnold BR, et al.
The Journal of Physical Chemistry A, 105(3), 537-543 (2001)
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
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