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1,4-Bis(isocyanatomethyl)benzene

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Identification
Molecular formula
C10H8N2O2
CAS number
2778-42-9
IUPAC name
1,4-bis(isocyanatomethyl)benzene
State
State

At room temperature, 1,4-Bis(isocyanatomethyl)benzene is in a solid state. However, it may exist in other forms such as a viscous liquid when slightly heated. It is important to maintain appropriate storage conditions to preserve its solid state at ambient temperatures.

Melting point (Celsius)
36.00
Melting point (Kelvin)
309.15
Boiling point (Celsius)
110.00
Boiling point (Kelvin)
383.15
General information
Molecular weight
174.18g/mol
Molar mass
174.1840g/mol
Density
1.1291g/cm3
Appearence

1,4-Bis(isocyanatomethyl)benzene is typically observed as a colorless to pale yellow solid. It forms crystalline structures and is characterized by a distinctive odor commonly associated with isocyanates. The appearance may slightly vary depending on its storage conditions.

Comment on solubility

Solubility of 1,4-bis(isocyanatomethyl)benzene

1,4-bis(isocyanatomethyl)benzene, also known as 4,4'-bis(isocyanatomethyl)diphenylmethane, exhibits interesting solubility characteristics in various solvents. Given its chemical structure, this compound is primarily characterized by the presence of isocyanate functional groups, which significantly influence its solubility profile.

Key points regarding the solubility of 1,4-bis(isocyanatomethyl)benzene include:

  • Solubility in Polar Solvents: This compound is generally soluble in polar solvents such as dimethyl sulfoxide (DMSO) and N,N-dimethylformamide (DMF), primarily due to the ability of the isocyanate groups to form hydrogen bonds with the solvent molecules.
  • Limited Solubility in Nonpolar Solvents: Conversely, it exhibits limited solubility in nonpolar solvents like hexane or benzene. The large aromatic structure contributes to its hydrophobic character, making it less compatible with nonpolar environments.
  • Influence of Temperature: The solubility of this compound can significantly vary with temperature, where higher temperatures generally enhance the solubility in both polar and nonpolar solvents due to increased molecular motion.
  • Reactivity Considerations: Due to the reactive nature of isocyanate groups, care must be taken when dissolving this compound, as it can react with moisture or amines present in some solvents, leading to the formation of urea derivatives.

In summary, the solubility of 1,4-bis(isocyanatomethyl)benzene is primarily dictated by its chemical structure and functional groups, presenting unique opportunities for its use in various chemical applications, especially in polymer and coating industries. Understanding the solubility behavior of this compound is essential for effective handling and application in research and industrial processes.

Interesting facts

Interesting Facts About 1,4-bis(isocyanatomethyl)benzene

1,4-bis(isocyanatomethyl)benzene, also known as m-bis(isocyanatomethyl)benzene, is a fascinating organic compound that belongs to the family of isocyanates. This compound is notable for several reasons:

  • Molecular Structure: The compound features a benzene ring substituted by two isocyanatomethyl groups at the 1 and 4 positions. This unique arrangement contributes to its reactivity and properties.
  • Applications: 1,4-bis(isocyanatomethyl)benzene is primarily used in the synthesis of polyurethanes and various other polymers. Its isocyanate functional groups are essential for cross-linking, which enhances the mechanical properties of these materials.
  • Industrial Relevance: Because of its application in the production of rigid and flexible foams, coatings, and elastomers, this compound plays a significant role in the construction, automotive, and furniture industries.
  • Toxicity: Like many isocyanates, 1,4-bis(isocyanatomethyl)benzene can be hazardous. Its vapors may be irritating to the respiratory tract, and therefore, proper safety measures should be implemented during handling.
  • Reactivity: The isocyanate group is highly reactive, making this compound a key player in various chemical reactions. It can react with amines, alcohols, and even water, leading to the formation of urea, carbamate, or even polyurethane linkages.

In summary, 1,4-bis(isocyanatomethyl)benzene is not just another compound; it's a building block in the realm of polymer chemistry. Its unique structure and reactivity make it an interesting subject of study for chemists and a vital ingredient in many industrial applications.

Synonyms
ISOCYANIC ACID, p-XYLYLENE ESTER
1014-98-8
1,4-xylylene diisocyanate
p-Xylylene isocyanate
p-xylylene diisocyanate
SCHEMBL21089
DTXSID60143907
NS00023060