4-[methyl(phenyl)carbamoyl]benzoic acid cas 153849-57-1

Physical and chemical properties

· Appearance: Usually a white to off-white crystalline powder.
· Melting point: The reported melting points in the literature are typically within the range of 185-190°C.
· Solubility:
· Due to its polar carboxylic acid and amide functional groups, it has a certain degree of solubility in polar organic solvents, such as dimethyl sulfoxide and N,N-dimethylformamide.
· Its solubility in alcohols such as methanol and ethanol is generally low.
· Its solubility in water is relatively low, but its carboxyl group can form salts with bases (such as sodium hydroxide) to form water-soluble salts.
· Acid-base property: The carboxyl group in the molecule gives it acidity, making it an organic acid.
Main purpose

4-[Methyl(phenyl)aminoformyl]benzoic acid is mainly used as an organic synthesis intermediate. Its value lies in the fact that the functional groups at both ends of the molecule can undergo different chemical reactions, thereby constructing more complex molecules.
1. Pharmaceutical Chemistry Intermediate:
· This structure is a key fragment for constructing certain kinase inhibitors (particularly for cancer treatment) and signal transduction inhibitors.
· One of the most notable applications is as an important intermediate in the synthesis of the anti-cancer drug dasatinib. Dasatinib is a multi-target tyrosine kinase inhibitor used to treat chronic myeloid leukemia and acute lymphoblastic leukemia. In the synthesis route of this drug, this compound or its derivatives undergo acylation or condensation reactions with another molecular fragment (such as 2-amino-6-chlorothiazole) through their carboxyl groups, forming the core skeleton of the drug molecule.
2. Materials Chemistry:
· It can be used as a building block for synthesizing liquid crystal materials or polymer polymers with specific functions. Its rigid rod-like structure and reactive termini make it suitable as a mesogenic element.
3. Ligand Chemistry:
· Both carboxylic acid and amide functional groups can serve as coordination sites and coordinate with metal ions, used for synthesizing metal-organic frameworks or other coordination compounds.
Chemical properties and reactions
· Reaction of carboxyl groups:
· Esterification/Acylamidation: The carboxyl group can undergo esterification reaction with alcohols, or form a new amide bond through condensation reaction with amines. This is the most crucial reaction as an intermediate.
· Salting: Reacting with inorganic bases to form water-soluble salts.
· Characteristics of amide bonds:
· The amide bond in this molecule is a tertiary amide, which has relatively stable chemical properties and is not prone to hydrolysis. This provides the possibility for selective modification of the carboxyl terminus.
Safety and Storage
· Hazard: Currently, there may not be fully detailed and publicly available toxicity data. As a chemical, it should be assumed to have some irritancy. Avoid inhaling dust and keep away from skin and eyes.
· Procedure: The operation must be carried out in a well-ventilated chemical fume hood and appropriate personal protective equipment should be worn, such as protective glasses, gloves and laboratory coat.
· Storage: It should be stored in a sealed manner in a cool, dry and dark place. It is usually recommended to store at room temperature or 2-8°C.
Summary
4-[Methyl(benzyl)aminoformyl]benzoic acid is a clearly defined and versatile organic synthetic building block. Its significance lies mainly in its role as a key intermediate for the potent anti-cancer drug dasatinib. The differential reactivity at both ends of its molecule (one end is an active carboxylic acid, and the other end is a stable tertiary amide) enables it to be efficiently and selectively used for the construction of complex drug molecules, making it a representative advanced intermediate in modern pharmaceutical industry.