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391980

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

functional group

nitrile

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000231507
BGBB7993V
BGBB4344V
04412TH
07112MH

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Inelastic and quasielastic neutron scattering and IR and R spectroscopic studies of 1, 2, 4, 5-tetracyanobenzene (TCNB)-1, 2, 4, 5-tetramethylbenzene (durene) complex.
Bator G, et al.
Phase Transitions, 80(6-7), 489-500 (2007)
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)
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)
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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