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Tetracyanoquinodimethane (TCNQ)

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Identification
Molecular formula
C12H4N4
CAS number
1518-16-7
IUPAC name
4-[4-(4-hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol
State
State

At room temperature, Tetracyanoquinodimethane is a solid. It's noted for its stability and ability to form various salts with intriguing conducting properties.

Melting point (Celsius)
286.00
Melting point (Kelvin)
559.15
Boiling point (Celsius)
355.00
Boiling point (Kelvin)
628.15
General information
Molecular weight
204.19g/mol
Molar mass
204.1900g/mol
Density
1.5060g/cm3
Appearence

Tetracyanoquinodimethane is a bright red crystalline solid. It is used in organic chemistry as a building block for charge-transfer complexes.

Comment on solubility

Solubility of 4-[4-(4-hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol

The solubility of 4-[4-(4-hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol can be influenced by several factors:

  • Polarity: The presence of functional groups like hydroxyl (-OH) and isocyano (−N≡C) may contribute to polarity, enhancing solubility in polar solvents.
  • Hydrogen Bonding: The -OH group can engage in hydrogen bonding, increasing solubility in both water and alcohols.
  • Solvent Compatibility: Typically, compounds with extensive aromatic systems may have better solubility in organic solvents such as ethanol, acetone, or dimethyl sulfoxide (DMSO) than in water.

However, it's important to note that due to the complex structure of this compound, solvent systems may yield varied solubility results depending on concentration and temperature. In general:

  1. The compound is expected to be sparingly soluble in water.
  2. It is likely to have higher solubility in organic solvents.

Understanding the solubility behavior of 4-[4-(4-hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol is key for its applications in various chemical processes, including synthesis and formulation of products.

Interesting facts

Interesting Facts About 4-[4-(4-Hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol

This compound is a fascinating example of a phenolic derivative, which plays a significant role in various chemical processes and applications. Here are some engaging insights:

  • Diverse Applications: Compounds like this one are often utilized in the production of polymers, fungicides, and pesticides, showcasing their versatility in both industrial and agricultural sectors.
  • Structure and Reactivity: The unique presence of both hydroxyl and isocyanide functional groups in its structure contributes to distinctive chemical reactivities. This opens the door for various transformation reactions that are of great interest in synthetic organic chemistry.
  • Biological Activity: Phenolic compounds are known for their significant biological activities, including antioxidant properties. Research into similar compounds has indicated potential therapeutic effects, making them of interest in medicinal chemistry.
  • Studying Isocyanides: The isocyanide moieties in this compound are particularly notable. Isocyanides are unique building blocks in organic synthesis; they participate in reactions like the Emmanuel reaction, which allows for the construction of complex molecular architectures.
  • Synthetic Pathways: Creating complex structures like this may involve multistep synthetic processes, often requiring innovative strategies that highlight a chemist's ingenuity in the lab.

In summary, 4-[4-(4-hydroxyphenyl)-2,3-diisocyano-buta-1,3-dienyl]phenol stands out not just for its intricate molecular framework but also for its potential applications and the rich chemistry it encapsulates. Exploring such compounds can reveal much about the interface of organic synthesis, materials science, and pharmaceutical development.

Synonyms
4-[4-(4-hydroxyphenyl)-2,3-diisocyanobuta-1,3-dienyl]phenol
AAA58074
NCI60_001506