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Lutidine

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Identification
Molecular formula
C9H13N
CAS number
2837-58-3
IUPAC name
2,3,5,6-tetramethylpyridine
State
State

At room temperature, 2,3,5,6-tetramethylpyridine is in a liquid state. It transitions from liquid to gas upon reaching its boiling point.

Melting point (Celsius)
-6.00
Melting point (Kelvin)
267.15
Boiling point (Celsius)
181.00
Boiling point (Kelvin)
454.15
General information
Molecular weight
135.22g/mol
Molar mass
135.2150g/mol
Density
0.8968g/cm3
Appearence

2,3,5,6-Tetramethylpyridine, also known as a type of lutidine, appears as a colorless liquid. It is a derivative of pyridine with four methyl groups attached at the 2, 3, 5, and 6 positions of the pyridine ring. The compound is generally colorless but can appear slightly yellowish due to impurities.

Comment on solubility

Solubility of 2,3,5,6-tetramethylpyridine

2,3,5,6-tetramethylpyridine, a member of the pyridine family, exhibits notable solubility characteristics that can be attributed to its molecular structure. Here are some key points regarding its solubility:

  • Solvent Preferences: 2,3,5,6-tetramethylpyridine is generally soluble in organic solvents such as ethanol, methanol, and chloroform.
  • Water Solubility: The compound has limited solubility in water. This is mainly due to its hydrophobic methyl groups, which make it less compatible with polar solvents.
  • Temperature Impact: As with many organic compounds, solubility may improve with increasing temperature, allowing for higher concentrations in suitable organic solvents.

“Like dissolves like” is a principle that holds true for 2,3,5,6-tetramethylpyridine; thus, it is more readily soluble in non-polar or slightly polar environments. Understanding the solubility of this compound helps in predicting its behavior in various chemical reactions and applications.

Interesting facts

Interesting Facts about 2,3,5,6-Tetramethylpyridine

2,3,5,6-tetramethylpyridine, often referred to as TMP, is an intriguing nitrogen-containing heterocyclic compound that showcases several fascinating characteristics.

Key Features of 2,3,5,6-Tetramethylpyridine:

  • Structural Versatility: This compound features a pyridine ring with four methyl groups occupying the 2, 3, 5, and 6 positions, enhancing its reactivity and solubility in various solvents.
  • Biochemical Significance: As a derivative of pyridine, TMP plays an important role in the synthesis of various pharmaceuticals and agrochemicals, making it a valuable compound in medicinal chemistry.
  • Catalytic Applications: Due to its unique electronic properties, 2,3,5,6-tetramethylpyridine is often used as a catalyst or a ligand in coordination chemistry, facilitating a range of organic reactions.
  • Analytical Use: This compound serves as a model compound for studying molecular interactions and is sometimes used in analytical techniques to evaluate the behavior of similar compounds.

Unique Characteristics:

The presence of methyl substituents enhances not only the steric profile of the compound but also its chemical stability, which is crucial for various industrial applications. The substituents can impact the electronic density of the nitrogen atom within the ring, influencing reactivity and interactions with other molecules.

As noted by several chemists, “the versatility of tetramethylpyridine makes it a compound of particular interest in both academic and industrial research.” This aligns with the ongoing investigations aimed at exploiting its unique properties in diverse areas of chemistry.

Conclusion:

2,3,5,6-tetramethylpyridine is more than just a simple organic compound; it represents a bridge between structure and function in the realm of chemistry. Its applications in synthesis, catalysis, and beyond make it a rich subject for further study and exploration.

Synonyms
2,3,5,6-TETRAMETHYLPYRIDINE
3748-84-3
Pyridine, 2,3,5,6-tetramethyl-
EINECS 223-149-5
SCHEMBL694204
DTXSID60190916
DB-391910
NS00030204