777897-67-3

Basic information

• Product Name: 2-fluoro-6-{[(4-methylphenyl)sulfonyl]amino}benzoic acid
• CAS NO: 777897-67-3
• Molecular Formula: C₁₄H₁₂FNO₄S
• Molecular Weight: 309.3128
• Mol File: 777897-67-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 470.1°C at 760 mmHg
• Flash Point: 238.1°C
• Density: 1.462g/cm³
• Vapor Pressure: 1.22E-09mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: 2-fluoro-6-{[(4-methylphenyl)sulfonyl]amino}benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-fluoro-6-{[(4-methylphenyl)sulfonyl]amino}benzoic acid(777897-67-3)
• EPA Substance Registry System: 2-fluoro-6-{[(4-methylphenyl)sulfonyl]amino}benzoic acid(777897-67-3)

Safety Data

• Hazardous Substances Data: 777897-67-3(Hazardous Substances Data)

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 445-29-4 o-fluoro-benzoic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 189075-69-2 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-fluorobenzamide 
• 1570135-07-7 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-fluoro-6-(4-methylphenylsulfonamido)benzamide 
• 393-52-2 2-Fluorobenzoyl chloride 
• 434-76-4 2-amino-6-fluorobenzoic acid 

Downstream Products

• 13198-87-3 N-(3-fluorophenyl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Late-Stage Amination of Drug-Like Benzoic Acids: Access to Anilines and Drug Conjugates through Directed Iridium-Catalyzed C?H Activation

The functionalization of C?H bonds, ubiquitous in drugs and drug-like molecules, represents an important synthetic strategy with the potential to streamline the drug-discovery process. Late-stage aromatic C?N bond–forming reactions are highly desirable, but despite their significance, accessing aminated analogues through direct and selective amination of C?H bonds remains a challenging goal. The method presented herein enables the amination of a wide array of benzoic acids with high selectivity. The robustness of the system is manifested by the large number of functional groups tolerated, which allowed the amination of a diverse array of marketed drugs and drug-like molecules. Furthermore, the introduction of a synthetic handle enabled expeditious access to targeted drug-delivery conjugates, PROTACs, and probes for chemical biology. This rapid access to valuable analogues, combined with operational simplicity and applicability to high-throughput experimentation has the potential to aid and considerably accelerate drug discovery.

Direct C-H amidation of benzoic acids to introduce meta- and para-amino groups by tandem decarboxylation

The Ir-catalyzed mild C-H amidation of benzoic acids with sulfonyl azides was developed to give reactions with high efficiency and functional-group compatibility. Subsequent protodecarboxylation of ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)aniline derivatives, the latter being inaccessible by other C-H functionalization approaches. The decarboxylation step was compatible with the amidation conditions, enabling a convenient one-pot, two-step process. Without a trace: Carboxylic acids are used as traceless directing groups in the Ir-catalyzed direct C-H amidation of arenes with sulfonyl azides under mild conditions. The tandem protodecarboxylation of the ortho-amidated benzoic acid products afforded meta- or para-substituted (N-sulfonyl)anilines, which are difficult to obtain by other C-H functionalization approaches.

Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles

A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.