19336-77-7

Basic information

• Product Name: 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID
• Synonyms: 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID;N-(4-Fluorophenyl)phthalamidic acid;2-{[(4-fluorophenyl)amino]carbonyl}benzoic acid
• CAS NO: 19336-77-7
• Molecular Formula: C₁₄H₁₀FNO₃
• Molecular Weight: 259.24
• Mol File: 19336-77-7.mol

Chemical Properties

• Boiling Point: 356.4°Cat760mmHg
• Flash Point: 169.4°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 1.07E-05mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID(19336-77-7)
• EPA Substance Registry System: 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID(19336-77-7)

Safety Data

• Hazardous Substances Data: 19336-77-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID is used as a chemical intermediate for the development of anti-inflammatory and analgesic drugs due to its structural features that may contribute to these therapeutic effects.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID is used as a starting material for the synthesis of more complex molecules with enhanced therapeutic applications, leveraging its unique structural elements to create novel pharmaceutical agents.
Used in Drug Discovery:
2-[(4-FLUOROPHENYL)CARBAMOYL]-BENZOIC ACID is utilized in drug discovery processes to explore its potential as a lead compound for the treatment of various conditions, given its capacity to be modified and optimized for specific biological targets.

InChI:InChI=1/C14H10FNO3/c15-9-5-7-10(8-6-9)16-13(17)11-3-1-2-4-12(11)14(18)19/h1-8H,(H,16,17)(H,18,19)

Upstream product

• 85-44-9 phthalic anhydride 
• 371-40-4 4-fluoroaniline 
• 88-99-3 benzene-1,2-dicarboxylic acid 

Relevant articles and documents

Synthetic strategy and antiviral evaluation of diamide containing heterocycles targeting dengue and yellow fever virus

High-Throughput screening of a subset of the CD3 chemical library (Centre for Drug Design and Discovery; KU Leuven) provided us with a lead compound 1, displaying low micromolar potency against dengue virus and yellow fever virus. Within a project aimed at discovering new inhibitors of flaviviruses, substitution of its central imidazole ring led to synthesis of variably substituted pyrazine dicarboxylamides and phthalic diamides, which were evaluated in cell-based assays for cytotoxicity and antiviral activity against the dengue virus (DENV) and yellow fever virus (YFV). Fourteen compounds inhibited DENV replication (EC50 ranging between 0.5 and 3.4 1/4M), with compounds 6b and 6d being the most potent inhibitors (EC50 0.5 1/4M) with selectivity indices (SI) > 235. Compound 7a likewise exhibited anti-DENV activity with an EC50 of 0.5 1/4M and an SI of >235. In addition, good antiviral activity of seven compounds in the series was also noted against the YFV with EC50 values ranging between 0.4 and 3.3 1/4M, with compound 6n being the most potent for this series with an EC50 0.4 1/4M and a selectivity index of >34. Finally, reversal of one of the central amide bonds as in series 13 proved deleterious to the inhibitory activity.

Compounds and methods for inducing chondrogenesis

The present invention provides compounds and compositions for the amelioration of arthritis and joint injuries by inducing mesenchymal stem cells into chondrocytes.

Water mediated, environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamides

Water mediated and environmentally friendly, step-wise, tandem & one-pot syntheses of 2-(1H-benzo[d]imidazole-2-yl)-N-arylbenzamide derivatives have been developed by simply combining phthalic anhydride, anilines and phenylenediammonium dihydrogenphosphate. This reaction has an easy workup, provides excellent yields, and uses water as the solvent which is considered to be relatively environmentally benign.

Chemoselective acylation of amines in aqueous media

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Microwave assisted synthesis of N-Arylphthalamic acids with hyperlipidemic activity

A series of substituted N-arylphthalamic acids 3a-i has been synthesized by the reaction of phthalic anhydride 1 and aryl- or heterocyclic amines 2a-i, in the absence of solvents, in a domestic microwave oven. The formation of nine N-arylphthalamic acids was accomplished in 1-3 min giving excellent yields for compounds 3a-g, but moderate yield of compounds 3h and 3i, respectively. Compounds 3h and 3i are new. Interestingly, N-arylphthalamic acids 3a-i induced hyperlipidemia in Swiss white mice and also increased animals' body weight.