185116-43-2

Basic information

• Product Name: FMOC-4-AMINOBENZOIC ACID
• Synonyms: FMOC-PABA-OH;FMOC-P-ABZ-OH;FMOC-4-AMINOBENZOIC ACID;FMOC-4-ABZ-OH;4-(FMOC-AMINO)BENZOIC ACID;4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINO-BENZOIC ACID;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-4-AMINOBENZOIC ACID;N-ALPHA-9-FLUORENYLMETHOXYCARBONYL-P-AMINOBENZOIC ACID
• CAS NO: 185116-43-2
• Molecular Formula: C₂₂H₁₇NO₄
• Molecular Weight: 359.37
• Product Categories: FMOC;Amino Acids;Unusual Amino Acids
• Mol File: 185116-43-2.mol
• Article Data: 10

Chemical Properties

• Melting Point: ~277 °C (dec.)
• Boiling Point: 544.854 °C at 760 mmHg
• Flash Point: 283.318 °C
• Appearance: /
• Density: 1.352 g/cm³
• Vapor Pressure: 1.05E-12mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: 2-8°C
• PKA: 4.29±0.10(Predicted)
• BRN: 7722986
• CAS DataBase Reference: FMOC-4-AMINOBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-4-AMINOBENZOIC ACID(185116-43-2)
• EPA Substance Registry System: FMOC-4-AMINOBENZOIC ACID(185116-43-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 185116-43-2(Hazardous Substances Data)

Usage

Description

FMOC-4-AMINOBENZOIC ACID, also known as 9-fluorenylmethoxycarbonyl-4-aminobenzoic acid, is a chemical compound that serves as a key building block in the synthesis of various organic molecules, particularly in the field of polymer chemistry. It is a white powder with unique chemical properties that make it suitable for use in the creation of complex molecular structures.

Uses

Used in Polymer Synthesis:
FMOC-4-AMINOBENZOIC ACID is used as a monomer in the improved rapid synthesis of oligo(benzamide) block copolymers. Its incorporation into these polymers enhances their structural diversity and functional properties, making them suitable for various applications in materials science and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, FMOC-4-AMINOBENZOIC ACID is used as a protecting group for the synthesis of various drugs and bioactive compounds. Its ability to protect specific functional groups during chemical reactions allows for the selective modification of target molecules, leading to the development of more effective and targeted therapeutic agents.
Used in Chemical Research:
FMOC-4-AMINOBENZOIC ACID is also utilized in chemical research as a versatile reagent for the synthesis of complex organic molecules. Its unique chemical properties enable the development of novel synthetic routes and methodologies, contributing to the advancement of organic chemistry and the discovery of new compounds with potential applications in various fields.

InChI:InChI=1/C22H17NO4/c24-21(25)14-9-11-15(12-10-14)23-22(26)27-13-20-18-7-3-1-5-16(18)17-6-2-4-8-19(17)20/h1-12,20H,13H2,(H,23,26)(H,24,25)

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 150-13-0 4-amino-benzoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 52407-60-0 dimethyl N-(4-amino-benzoyl)-L-glutamate 
• 218603-30-6 N-<4-carbonyl>pyridin-2-ylmethyl)>aminobenzoyl>-L-glutamate 
• 218603-08-8 dimethyl N-<4-benzoyl>-L-glutamate 
• 1011719-40-6 C₂₉H₂₇N₃O₅ 
• 1011719-43-9 C₃₅H₃₈N₄O₆ 
• 1011719-39-3 C₂₉H₂₇N₃O₅ 
• 1031755-95-9 pentafluorophenyl 4-[(9H-fluoren-9-yl)methoxycarbonylamino]benzoate 

Relevant articles and documents

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives

A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

Solid-phase synthesis of coralmycin A/epi-coralmycin A and desmethoxycoralmycin A

The total synthesis of the natural product coralmycin A/epi-coralmycin A, as well as a desmethoxy analogue is described. Synthesis was achievedviaa divergent, bidirectional solid-phase strategy, including a key on-resinO-acylation,OtoNacyl shift, andO-alkylation protocol to incorporate the unusual 4-amino-2-hydroxy-3-isopropoxybenzoic acid motifs. The synthetic natural product was generated as a 1?:?1 mixture of epimers at the central β-methoxyasparagine residue and exhibited potent antibacterial activity against a panel of ten Gram-negative and seven Gram-positive organisms. The desmethoxy analogue possessed significantly more potent antimicrobial activity against this panel with minimal inhibitory concentrations (MICs) as low as 50 nM.

Synthesis, biological evaluation, and docking studies of PAR2-AP-derived pseudopeptides as inhibitors of kallikrein 5 and 6

A series of protease activated receptor 2 activating peptide (PAR2-AP) derivatives (1-15) were designed and synthesized. The obtained compounds were tested on a panel of human kallikreins (hKLK1, hKLK2, hKLK5, hKLK6, and hKLK7) and were found completely i