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1,2,4,5-TETRACYANOBENZENE

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1,2,4,5-TETRACYANOBENZENE 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:
712-74-3
MF:
C10H2N4
MW:
178.15
Product Categories:
  • Building Blocks
  • C10 to C27
  • Chemical Synthesis
  • Cyanides/Nitriles
  • Nitrogen Compounds
  • Organic Building Blocks
  • Aromatic Nitriles
  • Functional Materials
  • Phthalonitriles & Naphthalonitriles
  • Phthalonitriles (Building Blocks for Phthalocyanines)
Mol File:
712-74-3.mol
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1,2,4,5-TETRACYANOBENZENE Chemical Properties

Melting point:
265-268 °C(lit.)
Boiling point:
300.36°C (rough estimate)
Density 
1.35 g/cm3
refractive index 
1.5200 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
acetone: soluble25mg/mL, clear, colorless to yellow
form 
powder to crystal
color 
White to Almost white
Water Solubility 
Soluble in water.
BRN 
1875027
Stability:
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
712-74-3(CAS DataBase Reference)
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Safety Information

Hazard Codes 
T
Risk 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
HS Code 
29269090

MSDS

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1,2,4,5-TETRACYANOBENZENE Usage And Synthesis

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.]

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