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Schiff base

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Identification
Molecular formula
C13H10BrNO
IUPAC name
2-[(4-bromophenyl)iminomethyl]phenol
State
State
Solid at room temperature as it is generally found in crystalline form.
Melting point (Celsius)
173.00
Melting point (Kelvin)
446.15
Boiling point (Celsius)
363.00
Boiling point (Kelvin)
636.15
General information
Molecular weight
278.13g/mol
Molar mass
278.1180g/mol
Density
1.6503g/cm3
Appearence

This compound typically appears as a yellow crystalline solid.

Comment on solubility

Solubility of 2-[(4-bromophenyl)iminomethyl]phenol

The solubility of 2-[(4-bromophenyl)iminomethyl]phenol is quite intriguing, given its unique structural features. This compound tends to exhibit limited solubility in water, which can be attributed to the presence of both hydrophobic aromatic rings and the polar functional groups in its structure. Key factors influencing its solubility include:

  • Hydrophobic Interactions: The two phenolic groups contribute to strong hydrophobic interactions, which often hinder solubility in polar solvents like water.
  • Hydrogen Bonding: The hydroxyl (-OH) group can form hydrogen bonds, making the compound more soluble in non-polar or slightly polar organic solvents.
  • Temperature Dependency: Increasing temperature may enhance solubility, as the kinetic energy helps overcome intermolecular interactions.

In practical terms, this means that while 2-[(4-bromophenyl)iminomethyl]phenol is not readily soluble in water, it can dissolve effectively in organic solvents such as ethanol, methanol, or chloroform. Therefore, for experimental purposes, using the appropriate solvent for dissolution is crucial.

As a guiding principle, it is often said that “like dissolves like,” and this compound exemplifies that notion. If one is working with 2-[(4-bromophenyl)iminomethyl]phenol, it is essential to choose solvents wisely to obtain the desired concentration and stability.

Interesting facts

Interesting Facts about 2-[(4-bromophenyl)iminomethyl]phenol

2-[(4-bromophenyl)iminomethyl]phenol is a fascinating compound that merges the worlds of organic chemistry and medicinal research, leading to various intriguing applications. Here are some notable aspects of this chemical:

  • Structure and Function: This compound features a distinctive imino group (–C=N–), which is crucial for its reactivity and potential biological activity. The presence of the bromine substituent on the aromatic ring enhances the compound's electronic properties, making it an interesting target for synthesis and study.
  • Pharmaceutical Relevance: The phenolic compound framework is crucial in drug discovery. Compounds like 2-[(4-bromophenyl)iminomethyl]phenol may serve as starting points for the development of new pharmaceuticals, especially in the area of antimicrobial therapies.
  • Versatile Applications: Beyond pharmaceuticals, such compounds can be utilized in various fields such as:
    • **Dyes and pigments** - due to the presence of conjugated systems.
    • **Agricultural chemicals** - as potential fungicides or herbicides.
    • **Polymeric materials** - by serving as monomers or additives that enhance material properties.
  • Synthetic Pathways: The synthesis of this compound often involves intricate organic reactions, showcasing the beauty of organic chemistry. Methods may include:
    1. Direct amidation reactions.
    2. Condensation techniques yielding imines.
    3. Bromination of phenolic substrates.
  • Research Potential: With ongoing studies into the biological activities of related compounds, 2-[(4-bromophenyl)iminomethyl]phenol may become a key player in understanding therapeutic mechanisms and exploring new pathways for treatment.

Overall, the exploration of 2-[(4-bromophenyl)iminomethyl]phenol can lead to exciting discoveries in chemistry and medicine. The compound stands as a testament to the intricate connections within organic compounds and their potential roles in advancing scientific knowledge and application.

Synonyms
2-(((4-Bromophenyl)imino)methyl)phenol
2-{[(4-bromophenyl)imino]methyl}phenol
2-[[(4-Bromophenyl)imino]methyl]phenol
654-940-7
alpha-(4-bromophenylimino)-ortho-cresol
886-34-0
Salicylidene p-bromoaniline
Phenol, o-(p-bromophenylformimidoyl)-
N-SALICYLIDENE P-BROMOANILINE
Salicylaldehyde 4-bromanil
2-{(E)-[(4-bromophenyl)imino]methyl}phenol
o-CRESOL, alpha-(p-BROMOPHENYLIMINO)-
2-[(4-bromophenyl)iminomethyl]phenol
53565-63-2
Phenol, o-(N-(p-bromophenyl)formimidoyl)-
Phenol, 2-(((4-bromophenyl)imino)methyl)-
2,4-Cyclohexadien-1-one, 6-[[(4-bromophenyl)amino]methylene]-
NSC-526319
.alpha.-(4-bromophenylimino)-o-cresol
82306-72-7
o-Cresol, .alpha.-(p-bromophenylimino)-
.alpha.-(4-Bromophenylimino)-ortho-cresol
Phenol, 2-[[(4-bromophenyl)imino]methyl]-
2-[(E)-[(4-bromophenyl)imino]methyl]phenol
Salicylidene-p-bromoaniline
Salicylidene-(p-bromoanil)
alpha-(4-Bromophenylimino)-o-cresol
NSC 526319
o-(N-(p-Bromophenyl)formimidoyl)phenol
MFCD00020088
NSC526319
Enamine_001248
WLN: QR B1UNR DE
8M9U8EX2WE
N-salicylidene-4-bromoaniline
SCHEMBL5784154
N-(p-Bromophenyl)salicylaldimine
DTXSID00419774
VWAMOQWOPYDCQR-OQLLNIDSSA-N
VWAMOQWOPYDCQR-UHFFFAOYSA-N
DTXSID601282790
HMS1397I16
STK926113
AKOS000591435
AKOS004906530
4-Bromo-N-(2-hydroxybenzylidene)aniline
BS-10363
Phenol, o-[N-(p-bromophenyl)formimidoyl]
CS-0326085
(E)-2-(((4-Bromophenyl)imino)methyl)phenol
2-((E)-[(4-Bromophenyl)imino]methyl)phenol #
phenol, 2-[(E)-[(4-bromophenyl)imino]methyl]-
Z56791249