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Michler's base

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Identification
Molecular formula
C17H20N2
CAS number
101-61-1
IUPAC name
4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethyl-aniline
State
State

Michler's base is typically in a solid state at room temperature, appearing as crystalline solid that may darken over time if exposed to environmental conditions such as light or air.

Melting point (Celsius)
84.00
Melting point (Kelvin)
357.15
Boiling point (Celsius)
192.00
Boiling point (Kelvin)
465.15
General information
Molecular weight
268.36g/mol
Molar mass
268.3630g/mol
Density
1.2400g/cm3
Appearence

Michler's base appears as colorless to pale yellow crystals or crystalline powder. It tends to darken upon exposure to light. Due to its chromophoric properties, it is often associated with dyes and colorants as an intermediate, but the compound itself is not strongly colored.

Comment on solubility

Solubility of 4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethyl-aniline

The solubility of 4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethyl-aniline is influenced by several factors, primarily due to its structural characteristics.

Typically, the solubility of organic compounds, such as this one, can be affected by:

  • Polarity: Compounds containing polar functional groups tend to be more soluble in polar solvents.
  • Molecular Weight: Higher molecular weights may result in decreased solubility due to increased van der Waals interactions.
  • Hydrogen Bonding: The ability to form hydrogen bonds can enhance solubility in specific solvents, particularly water.

This compound possesses dimethylamino and carboximidoyl groups, which might suggest moderate to high solubility in polar solvents such as water or alcohols. However, its overall solubility profile may also reflect its less polar regions, which can hinder solubility depending on the solvent choice.

In general, it could be hypothesized that:

  • In water: Moderate solubility expected due to potential hydrogen bonding.
  • In organic solvents: Reactivity-driven solubility could vary based on solvent polarity.
  • In acidic or basic solutions: Altered solubility based on protonation or deprotonation of functional groups.

As a final note, experimental data is crucial to accurately determine solubility, as theoretical estimations may not capture all nuances of solubility behavior in real-world scenarios.

Interesting facts

Interesting Facts about 4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethyl-aniline

This compound, often found in various chemical studies, possesses a unique combination of structural features that make it particularly fascinating for both research and application. Below are some intriguing aspects of this compound:

  • Diverse Applications: Due to its structural properties, this compound can serve as a building block in organic synthesis, particularly in the development of dyes and pigments.
  • Photophysical Properties: The presence of the dimethylamino group often imparts interesting electronic properties, allowing this compound to exhibit significant fluorescence characteristics, which are valuable in various sensing applications.
  • Therapeutic Potential: Compounds that feature similar amine structures have been studied for their biological activities, suggesting potential for development in pharmaceuticals as well as biological probes.
  • Chemical Reactivity: This compound can engage in various chemical reactions, including nucleophilic substitutions, leading to versatile products that are important in materials science.
  • Historical Context: Compounds with similar frameworks have been instrumental in the chemical revolution, contributing to advancements in synthetic methodologies and expanding the horizons of organic chemistry.
  • Challenges in Synthesis: The multi-step synthesis of this compound can be complex, making it a subject of study for aspiring chemists seeking to understand reaction mechanisms and methodologies.

In conclusion, 4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethyl-aniline stands out as a compelling example of how fundamental chemical principles can lead to a wealth of applications and research opportunities. Its intricate design invites exploration and study, supporting the continued evolution of chemical science.

Synonyms
AURAMINE
Auramine base
Auramine O base
Auramine N base
Auramine OO
Auramine SS
Auramine OAF
C.I. Solvent Yellow 34
Waxoline Yellow O
Solvent Yellow 34
RCRA waste number U014
Caswell No. 063A
4,4'-Carbonimidoylbis(N,N-dimethylaniline)
CCRIS 58
auramine O free base
Auremine
HSDB 2935
EINECS 207-762-5
EPA Pesticide Chemical Code 039501
BRN 2215338
Benzenamine, 4,4'-carbonimidoylbis(N,N-dimethyl-
UNII-73O74R443B
CHEBI:51874
AI3-17282
AURAMINE [IARC]
C.I. Basic Yellow 2, Free Base
Benzenamine, 4,4'-carbonimidoylbis[N,N-dimethyl-
Benzophenoneidum (Salt/Mix)
Auramine Yellow (Salt/Mix)
Basic Yellow 2 (Salt/Mix)
DTXSID7043821
Tetramethyldiaminodiphenylacetimine
Auramine hydrochloride (Salt/Mix)
4-14-00-00256 (Beilstein Handbook Reference)
AURAMINE (IARC)
Auramine (VAN)
4,4'-carbonimidoylbis[N,N-dimethylaniline]
BENZENAMINE, 4,4'-(CARBONIMIDOYLBIS(N,N-DIMETHYL-
BENZENAMINE, 4,4'-(CARBONIMIDOYLBIS[N,N-DIMETHYL-
DTXCID5023821
4,4'Dimethylaminobenzophenonimide
Tetramethylpdiaminoimidobenzophenone
Bis(pdimethylaminophenyl)methyleneimine
Aniline, 4,4'imidocarbonylbis(N,Ndimethyl
4,4'(Imidocarbonyl)bis(N,Ndimethylaniline)
4,4'Carbonimidoylbis(N,Ndimethylbenzenamine)
Benzenamine, 4,4'carbonimidoylbis(N,Ndimethyl
4,4-(IMIDOCARBONYL)BIS(N,N-DIMETHYLANILINE)
ANILINE, 4,4'-IMINOCARBONYLBIS(N,N-DIMETHYL-
jpiyztwmugtehx-uhfffaoysa-n
un3077
492-80-8
Yellow pyoctanine
Glauramine
Apyonine auramine base
Auramine (free base)
4,4'-Dimethylaminobenzophenonimide
4,4'-(Imidocarbonyl)bis(N,N-dimethylaniline)
CI Solvent Yellow 34
CI Basic Yellow 2, free base
Bis(p-dimethylaminophenyl)methyleneimine
Tetramethyl-p-diamino-imido-benzophenone
4-[4-(dimethylamino)benzenecarboximidoyl]-N,N-dimethylaniline
C.I. 41000B
CI 41000B
Aniline, 4,4'-imidocarbonylbis(N,N-dimethyl-
4,4'-Carbonimidoylbis(N,N-dimethylbenzenamine)
Aniline, 4,4'-(imidocarbonyl)bis(N,N-dimethyl-
73O74R443B
4,4'-(Iminomethylene)bis(N,N-dimethylaniline)
Auramine manufacture
Auramine, manufacture of
Auramine, technical-grade
RCRA waste no. U014
Yellowpyoctanine
Auramine free base
Oprea1_256545
SCHEMBL95306
Auramine, analytical standard
CHEMBL1626329
4,4'-Dimethylaminobenzophenone imine
MFCD00036224
STK525871
AKOS003193920
NCGC00091235-02
PD171473
NS00079853
EN300-33932
C19193
BIS(P-DIMETHYLAMINOPHENYL)METHYLENEIMINE [HSDB]
Q26840770