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Phenylenediamine

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Identification
Molecular formula
C6H8N2
CAS number
95-54-5 (o-phenylenediamine); 108-45-2 (m-phenylenediamine); 106-50-3 (p-phenylenediamine)
IUPAC name
benzene-1,2-diamine;benzene-1,3-diamine;benzene-1,4-diamine
State
State

At room temperature, phenylenediamines are solid. They are typically handled in the form of crystals or flakes, and are stable under normal conditions.

Melting point (Celsius)
63.00
Melting point (Kelvin)
336.15
Boiling point (Celsius)
267.00
Boiling point (Kelvin)
540.15
General information
Molecular weight
108.15g/mol
Molar mass
108.1540g/mol
Density
1.2410g/cm3
Appearence

Phenylenediamines are usually white to slightly colored crystalline solids. They may appear as needles or prisms, and can turn reddish upon exposure to air and light due to oxidation.

Comment on solubility

Solubility of Benzene-1,2-diamine, Benzene-1,3-diamine, and Benzene-1,4-diamine

The solubility of a compound plays a crucial role in determining its practical applications, particularly in the fields of pharmaceuticals and organic synthesis. For the diamines derived from benzene, namely benzene-1,2-diamine, benzene-1,3-diamine, and benzene-1,4-diamine, the solubility characteristics can be summarized as follows:

  • General Trend: The presence of amino groups in these compounds enhances their ability to interact with polar solvents, contributing to their solubility in certain conditions.
  • Solvent Specificity:
    • Benzene-1,2-diamine: Offers moderate solubility in water, primarily due to its two amino groups.
    • Benzene-1,3-diamine: Exhibits similar solubility patterns, easily dissolving in polar solvents while remaining less soluble in nonpolar solvents.
    • Benzene-1,4-diamine: Displays a slightly lower solubility in water compared to the other two due to differences in molecular structure affecting hydrogen bonding capabilities.
  • Temperature Influence: Increased temperature generally enhances solubility for these diamines in polar solvents, making them more accessible for reactions and formulations.

In conclusion, while all three compounds show reasonable solubility in polar solvents, their specific solubility can differ significantly based on the positional isomerism of the amino groups. Understanding these variations is essential for their effective use in industrial and laboratory settings.

Interesting facts

Benzene-1,2-diamine (o-phenylenediamine)

Benzene-1,2-diamine, commonly known as o-phenylenediamine, is a fascinating compound with significant applications in various fields:

  • Industrial Use: It is widely utilized in the production of dyes and pigments, especially in the textile and rubber industries.
  • Health Applications: O-phenylenediamine is also used in the manufacturing of certain pharmaceuticals and as a component in hair dyes.
  • Safety Considerations: This compound exhibits properties that can cause skin and respiratory irritation; thus, proper safety measures are crucial when handling it.

As reported in chemical literature, "Its ability to act as a reducing agent contributes to its utility across various synthesis processes." This feature allows for its involvement in redox reactions, making it an interesting compound for study.

Benzene-1,3-diamine (m-phenylenediamine)

Benzene-1,3-diamine, or m-phenylenediamine, has distinct properties that make it particularly interesting:

  • Versatility: This compound is employed in the production of rubber accelerators and anti-ozonants, which enhance the durability of rubber products.
  • Applications in Colorants: It is also a precursor to various food colorants and is utilized in textile dye manufacturing.
  • Research Resilience: Known for its resilience in chemical processes, m-phenylenediamine has been the subject of numerous studies exploring its reactivity and properties.

In the words of chemists, "Understanding the reactivity of m-phenylenediamine opens up avenues for innovative synthetic pathways." This highlights its importance in organic synthesis.

Benzene-1,4-diamine (p-phenylenediamine)

Benzene-1,4-diamine, or p-phenylenediamine, is another notable compound in the realm of organic chemistry:

  • Cosmetic Uses: This compound is famously used in many hair dye formulations due to its excellent color stability.
  • Polymer Formation: It serves as a building block for producing polyamide fibers, which are valued for their strength and resilience.
  • Caution Required: Similar to its isomers, p-phenylenediamine poses health risks, including potential allergenic reactions, underlining the importance of safety assessment in its use.

As noted in safety studies, "The structural characteristics of p-phenylenediamine enhance its bonding capabilities, making it crucial for various industrial applications." This underscores its vital role in material science and chemistry.

Synonyms
25265-76-3
TJX894Z2PK
BENZENE, DIAMINO
RefChem:861724
PHENYLENEDIAMINE [VANDF]
CHEBI:51402
DTXSID901057112
607-676-1
25265-76-3 108-45-2
BENZENEDIAMINE
Diaminobenzene
Phenylenediamine
UNII-TJX894Z2PK
benzene-1,2-diamine;benzene-1,3-diamine;benzene-1,4-diamine
SCHEMBL37040
LGZPGNGUUUOHAI-UHFFFAOYSA-N