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Phthalonitrile

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Identification
Molecular formula
C8H4N2
CAS number
91-15-6
IUPAC name
phthalonitrile
State
State

Phthalonitrile is a solid at room temperature.

Melting point (Celsius)
139.00
Melting point (Kelvin)
412.15
Boiling point (Celsius)
294.00
Boiling point (Kelvin)
567.15
General information
Molecular weight
128.13g/mol
Molar mass
128.1310g/mol
Density
1.1904g/cm3
Appearence

Phthalonitrile is a white to light yellow crystalline solid. It appears as needle-like crystals and is often used as a precursor to phthalocyanine dyes and pigments.

Comment on solubility

Solubility of Phthalonitrile

Phthalonitrile, with the chemical formula C8H4N2, exhibits unique solubility characteristics that are essential for its applications in various chemical processes. Understanding its solubility can aid in optimizing its use in different scenarios.

Solubility Characteristics:

  • Solvent Dependence: Phthalonitrile is known to be soluble in organic solvents such as acetonitrile, ethanol, and dimethylformamide (DMF). However, it is generally insoluble in water, which is a common feature of many nitrile compounds due to the lack of hydrogen bonding.
  • Temperature Effect: Like many organic compounds, the solubility of phthalonitrile tends to increase with temperature. This can be advantageous when higher concentrations are necessary for specific reactions.
  • Intermolecular Interactions: The solubility behavior can be attributed to specific intermolecular forces, including dipole-dipole interactions and van der Waals forces. Its rigid structure limits its flexibility, impacting how well it can dissolve in various solvents.

In summary, while phthalonitrile demonstrates limited solubility in polar solvents like water, it readily dissolves in a range of organic solvents, providing a useful toolkit for chemists working with this compound. Understanding these solubility properties is crucial for effective application in synthesis and industrial processes.

Interesting facts

Interesting Facts about Phthalonitrile

Phthalonitrile, a fascinating compound in the realm of organic chemistry, holds significant importance due to its versatile applications and unique structural properties. Here are some engaging facts about this intriguing compound:

  • Structure: Phthalonitrile features a rigid and planar structure, characterized by two cyano groups attached to a aromatic ring. This structure enhances its stability and reactivity, making it suitable for various chemical transformations.
  • Applications: This compound serves as a key building block in the synthesis of polymers, dyes, and various pharmaceuticals. Its derivatives play crucial roles in the production of high-performance materials, including resins and coatings.
  • Formation of Phthalocyanines: One remarkable aspect of phthalonitrile is its ability to react and form phthalocyanines, which are complex macrocyclic compounds extensively used as dyes and pigments in the textile and printing industries.
  • Electrochemical Properties: Phthalonitrile exhibits interesting electrochemical properties, enabling its use in the development of sensors and electrochromic devices. These characteristics allow for innovative applications in environmental monitoring and advanced electronic systems.
  • Sustainability: Research is ongoing to explore more sustainable methods of synthesizing phthalonitrile and its derivatives, promoting ecological awareness in chemical manufacturing processes.

As a versatile compound with a rich chemistry, phthalonitrile continues to offer opportunities for research and development, solidifying its place in both organic synthesis and industrial applications. As chemists strive for greater sustainability, compounds like phthalonitrile could play a pivotal role in advancing greener technologies.

Synonyms
Phthalonitrile
1,2-Dicyanobenzene
91-15-6
Phthalodinitrile
o-Phthalodinitrile
1,2-BENZENEDICARBONITRILE
o-Dicyanobenzene
1,2-Benzodinitrile
benzene-1,2-dicarbonitrile
o-Cyanobenzonitrile
o-Benzenedinitrile
o-Benzenedicarbonitrile
o-Pdn
Phthalic acid dinitrile
Ftalodinitril
Ftalonitril
USAF ND-09
ortho-Dicyanobenzene
Ftalonitril [Czech]
Ftalodinitril [Czech]
1,2-Benzendikarbonitril
NSC 17562
CCRIS 8898
HSDB 5273
EINECS 202-044-8
1,2-BIS(CYANO)BENZENE
DTXSID8029604
AI3-00049
978627YAJU
NSC-17562
DTXCID709604
EC 202-044-8
1,2-BENZENEDICARBONITRILE [HSDB]
O-PHTHALONITRILE
1,2-Benzendikarbonitril [Czech]
oDicyanobenzene
UNII-978627YAJU
o-benzodinitrile
oBenzenedinitrile
oPhthalodinitrile
oCyanobenzonitrile
orthodicyanobenzene
1,2Benzodinitrile
1,2Dicyanobenzene
MFCD00001771
oBenzenedicarbonitrile
1, 2-Dicyanobenzene
1,2Benzendikarbonitril
WLN: NCR BCN
SCHEMBL57480
1,2-Dicyanobenzene, 98%
PHTHALIC ACID, DINITRILE
CHEMBL3185350
CHEBI:232056
NSC17562
Tox21_200999
STK802328
AKOS000120698
CS-W016553
FP62498
CAS-91-15-6
NCGC00248893-01
NCGC00258552-01
AC-14597
DB-030219
NS00009417
P0404
EN300-21053
D70390
Q408783
F0001-2216
Z104486876
202-044-8