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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000231507
BGBB7993V
BGBB4344V
04412TH
07112MH

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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)
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)
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