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Michler's ketone

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Identification
Molecular formula
C17H20N2
CAS number
90-94-8
IUPAC name
N,N,N',N'-tetramethyl-1,1-diphenyl-methanediamine
State
State
At room temperature, it is found as a solid.
Melting point (Celsius)
179.50
Melting point (Kelvin)
452.65
Boiling point (Celsius)
399.90
Boiling point (Kelvin)
673.05
General information
Molecular weight
268.39g/mol
Molar mass
268.3890g/mol
Density
1.0740g/cm3
Appearence

The compound typically appears as a colorless to pale yellow crystalline solid.

Comment on solubility

Solubility of N,N,N',N'-Tetramethyl-1,1-diphenyl-methanediamine

N,N,N',N'-Tetramethyl-1,1-diphenyl-methanediamine, often abbreviated as TMEDA, exhibits intriguing solubility characteristics that make it an interesting compound in chemical applications. Here are some key points regarding its solubility:

  • Polar and Nonpolar Solvents: TMEDA is soluble in a variety of organic solvents, primarily due to its nonpolar alkyl segments and polar amine functionalities.
  • Aromatic Solubility: It shows good solubility in aromatic hydrocarbons, such as toluene and xylene, which is advantageous for reactions requiring nonpolar environments.
  • Water Solubility: TMEDA's solubility in water is limited owing to its hydrophobic character, making it less favorable for aqueous applications.
  • Temperature Effects: Solubility can also depend on temperature; generally, increasing temperature enhances solubility for many organic compounds, including TMEDA.

To summarize, while TMEDA is relatively soluble in organic solvents, its limited water solubility reflects its overall hydrophobic nature. In application, the choice of solvent largely influences its usability, making a proper selectivity for solvents crucial in chemical reactions and processes.

Interesting facts

Interesting Facts about N,N,N',N'-Tetramethyl-1,1-diphenyl-methanediamine

N,N,N',N'-Tetramethyl-1,1-diphenyl-methanediamine, often abbreviated as TMDPA, is a fascinating compound that has captured the attention of chemists due to its unique structural features and diverse applications. Here are some intriguing insights:

  • Structure and Symmetry: TMDPA features a central methanediamine core flanked by two diphenyl groups. This structure contributes to its interesting electronic properties, making it a subject of study in organic and materials chemistry.
  • Redox Properties: The compound is known for its redox-active nature. It can undergo oxidation and reduction processes, which is particularly useful in the development of organic electronics and as a component in electrochemical sensors.
  • Applications in Dyes: Due to its chromophoric properties, TMDPA has potential applications in the dye industry. Its ability to absorb and emit light makes it suitable for use in various coloring agents and fluorescent materials.
  • Role in Polymer Science: TMDPA is often used as an antioxidant in rubber and plastic formulations. Its ability to scavenge free radicals helps in prolonging the life and stability of these materials.
  • Research Interest: Scientists are investigating its potential roles in biological systems, particularly as a redox catalyst. This opens avenues for exploring greener synthesis techniques in organic chemistry.
  • Quote from Research: “The unique properties of TMDPA make it a valuable asset in both industrial applications and scientific research, bridging the gap between organic chemistry and material science.”

This compound not only enhances our understanding of chemical interactions but also serves as a multifaceted tool for innovation. Its versatility is a testament to the complexity and interconnectivity of chemical science.

Synonyms
BRN 2053121
N,N,N',N'-Tetramethyl-1,1-diphenylmethanediamine
METHANEDIAMINE, 1,1-DIPHENYL-N,N,N',N'-TETRAMETHYL-
N,N,N',N'-Tetramethyldiaminodiphenylmethane
DTXSID00172635
DTXCID0095126
RefChem:352166
19111-89-8
SCHEMBL2478431
N,N'-tetramethyldiamino-diphenylmethane