· CAS Number: 10252-63-8
· Chemical Name: 4-(Methylamino sulfonyl)benzoic acid
· Common Name: N-Methylsulfanilobenzoic acid
· Molecular Formula: C₈H₉NO₄S
· Molecular Weight: 215.22 g/mol
Chemical structure and properties
· Structural features: The molecular structure consists of three key parts:
1. A phenylacetic group: It provides a carboxylic acid (-COOH) functional group, giving it acidity and serving as a derivatization site.
2. A sulfonamide group: It is the bridge connecting the benzene ring and the methyl group, with a structure of -SO₂NHCH₃, which is a key pharmacophore in many drug molecules.
3. A methyl group: It is attached to the nitrogen atom of the sulfonamide.
· Appearance: It is usually white or off-white crystalline powder.
· Melting point: Literature reports a melting point of approximately 238-240 °C.
· Solubility:
· Due to the presence of the carboxyl group, it is soluble in alkaline aqueous solutions (such as sodium hydroxide, sodium bicarbonate solutions), forming water-soluble salts.
· It may precipitate in strong acids.
· It has some solubility in common organic solvents (such as ethanol, dimethyl sulfoxide, DMF), but its solubility in water is very low.
Main Uses and Applications
4-(Methylamino sulfonyl)benzoic acid is an important pharmaceutical intermediate and chemical building block.
1. Pharmaceutical synthetic intermediates:
· This is its most core and important application. Its structure combines the sulfonamide and benzoic acid functional groups, which are two extremely important functional groups in medicinal chemistry.
· The sulfonamide group is a characteristic structure of many carbonic anhydrase inhibitors and sulfonamide drugs. These drugs have various pharmacological activities such as diuresis, lowering intraocular pressure (for glaucoma), and anti-epilepsy.
· This compound can serve as a key starting material or intermediate for the synthesis of more complex active pharmaceutical molecules. Researchers can use its carboxyl group for esterification, amidation, etc., or utilize the sulfonamide nitrogen atom for further alkylation to optimize the physicochemical properties and biological activity of the drug.
2. Chemical research:
· In academic and industrial research and development, it is used as a key structural unit for constructing complex molecules.
· It can be used for structure-activity relationship studies to help understand how sulfonamide compounds produce pharmacological effects by interacting with enzymes (such as carbonic anhydrase).
Safety and Storage
· Hazard: As a chemical substance, it is presumed to have potential irritancy to the body. It may cause irritation to the eyes, skin and respiratory tract. Swallowing or inhaling it may be harmful.
· Stability: It is stable at normal temperature and pressure in a dry environment.
· Storage: It should be stored sealed in a cool, dry and well-ventilated place, away from fire sources and incompatible strong oxidants.
Summary
CAS 10252-63-8 (4-(Methylamino sulfonyl)benzoic acid) is an important pharmaceutical intermediate with dual functional groups of sulfonamide and benzoic acid. It is not usually used directly as a drug, but its structure serves as the core framework for designing and synthesizing various pharmacologically active molecules (especially carbonic anhydrase inhibitor drugs). It has clear application value in pharmaceutical chemistry laboratories and fine chemical production.
