6952-12-1

Basic information

• Product Name: 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID
• Synonyms: 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID;4-(Methylamino)salicylic acid;NSC 63019;Benzoic acid,2-hydroxy-4-(methylamino)-
• CAS NO: 6952-12-1
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.163
• Mol File: 6952-12-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 126-127℃ (benzene )
• Boiling Point: 368°Cat760mmHg
• Flash Point: 176.3°C
• Appearance: /
• Density: 1.394g/cm³
• Vapor Pressure: 4.6E-06mmHg at 25°C
• Refractive Index: 1.668
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID(6952-12-1)
• EPA Substance Registry System: 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID(6952-12-1)

Safety Data

• Hazardous Substances Data: 6952-12-1(Hazardous Substances Data)

Usage

General Description

2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID, also known as p-Toluic acid, is a chemical compound with the molecular formula C8H9NO3. It is a white crystalline solid that is often used in the production of pharmaceuticals, dyes, and pigments. It is a derivative of benzoic acid and contains a hydroxyl group and a methylamino group on the benzene ring. 2-HYDROXY-4-(METHYLAMINO)BENZOIC ACID has a wide range of applications in various industries and is an important building block in organic synthesis. It is also used in the production of hair dyes and some cosmetic products.

InChI:InChI=1/C8H9NO3/c1-9-5-2-3-6(8(11)12)7(10)4-5/h2-4,9-10H,1H3,(H,11,12)

Upstream product

• 14703-69-6 3-(N-methylamino)phenol 
• 65-49-6 4-Aminosalicylic acid 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1246518-47-7 1-(4-carboxy-3-hydroxy-N-methylphenylaminomethyl)-benzotriazole 

Relevant articles and documents

Synthesis and biological evaluation of orally active prodrugs and analogs of para-aminosalicylic acid (PAS)

Tuberculosis (TB) is one of the world's most deadly infectious diseases resulting in nearly 1.3 million deaths annually and infecting nearly one-quarter of the population. para-Aminosalicylic acid (PAS), an important second-line agent for treating drug-resistant Mycobacterium tuberculosis, has moderate bioavailability and rapid clearance that necessitate high daily doses of up to 12 g per day, which in turn causes severe gastrointestinal disturbances presumably by disruption of gut microbiota and host epithelial cells. We first synthesized a series of alkyl, acyloxy and alkyloxycarbonyloxyalkyl ester prodrugs to increase the oral bioavailability and thereby prevent intestinal accumulation as well as undesirable bioactivation by the gut microbiome to non-natural folate species that exhibit cytotoxicity. The pivoxyl prodrug of PAS was superior to all of the prodrugs examined and showed nearly quantitative absorption. While the conceptually simple prodrug approach improved the oral bioavailability of PAS, it did not address the intrinsic rapid clearance of PAS mediated by N-acetyltransferase-1 (NAT-1). Thus, we next modified the PAS scaffold to reduce NAT-1 catalyzed inactivation by introduction of groups to sterically block N-acetylation and fluorination of the aryl ring of PAS to attenuate N-acetylation by electronically deactivating the para-amino group. Among the mono-fluorinated analogs prepared, 5-fluoro-PAS, exhibited the best activity and an 11-fold decreased rate of inactivation by NAT-1 that translated to a 5-fold improved exposure as measured by area-under-the-curve (AUC) following oral dosing to CD-1 mice. The pivoxyl prodrug and fluorination at the 5-position of PAS address the primary limitations of PAS and have the potential to revitalize this second-line TB drug.