126695-58-7

Basic information

• Product Name: 4-Azido-2,3,5,6-tetrafluorobenzoicacid
• Synonyms: Succinimidylester(ATFB,SE);4-Azido-2,3,5,6-tetrafluorobenzoic Acid, N-Succinimidyl Ester, ATFB SE;ATFB, SE [4-Azido-2,3,5,6-tetrafluorobenzoic acid, succiniMidyl ester]
• CAS NO: 126695-58-7
• Molecular Formula: C₁₁H₄F₄N₄O₄
• Molecular Weight: 0
• Product Categories: Nitric Oxide Reagents;Cross Linking Reagents;Photoaffinity Labels
• Mol File: 126695-58-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 104-105°C
• Appearance: /
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Stability: Light and Moisture Sensitive. Store in freezer
• CAS DataBase Reference: 4-Azido-2,3,5,6-tetrafluorobenzoicacid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Azido-2,3,5,6-tetrafluorobenzoicacid(126695-58-7)
• EPA Substance Registry System: 4-Azido-2,3,5,6-tetrafluorobenzoicacid(126695-58-7)

Safety Data

• RIDADR: UN 1325 4.1/PG III
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 126695-58-7(Hazardous Substances Data)

Usage

Description

4-Azido-2,3,5,6-tetrafluorobenzoic acid is a fluorinated aryl azide that exists as colorless needles. It is characterized by its photoreactive properties and strong absorption at 273 nm with an extinction coefficient (e) of 23 x 10^-3.

Uses

Used in Photofunctionalization Applications:
4-Azido-2,3,5,6-tetrafluorobenzoic acid is used as a photofunctionalization agent for polymer surfaces. Its strong absorption at 273 nm allows for efficient photochemical reactions on the surface, enabling the creation of new functional groups or the attachment of other molecules.
Used in Chemical Research:
4-Azido-2,3,5,6-tetrafluorobenzoic acid is used as a non-fluorescent heterobifunctional, photoreactive crosslinking probe in chemical research. Its photoreactive properties allow for the formation of covalent bonds between molecules upon exposure to light, making it a valuable tool for studying molecular interactions and structures.
Used in Material Science:
In the field of material science, 4-Azido-2,3,5,6-tetrafluorobenzoic acid is used for the photofunctionalization of polymer surfaces. This allows for the modification of surface properties, such as wettability, adhesion, or biocompatibility, which can be crucial for various applications, including sensors, coatings, or biomedical devices.

InChI:InChI=1/C11H4F4N4O4/c12-6-5(7(13)9(15)10(8(6)14)17-18-16)11(22)23-19-3(20)1-2-4(19)21/h1-2H2

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 122590-77-6 4-azido-2,3,5,6-tetrafluorobenzoic acid 
• 122590-75-4 methyl 4-azidotetrafluorobenzoate 
• 122616-98-2 4-azidotetrafluorobenzamide 
• 36629-42-2 methyl pentafluorobenzoate 
• 602-94-8 Pentafluorobenzoic acid 
• 652-31-3 2,3,4,5,6-pentafluorobenzamide 
• 773-82-0 Pentafluorobenzonitrile 
• 715-37-7 methyl 4-amino-2,3,5,6-tetrafluorobenzoate 

Downstream Products

• 254968-74-6 12-[N-(4-azido-2,3,5,6-tetrafluorobenzoyl)]amidododecanoic acid 
• 215873-25-9 (C₄H₄NO₂OOC)C₆F₄NP(C₆H₅)2CH₂P(C₆H₅)2 
• 165898-22-6 2-(4-azido-2,3,5,6-tetrafluorobenzamido)-6-[5-(hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-6-yl)pentanamido]hexanoic acid 
• 158871-73-9 C₇₁H₄F₄N₂O₄ 
• 146672-33-5 N^ε-(4-azido-2,3,5,6-tetrafluorobenzoyl)-N^α-Boc-L-lysine 
• 249749-25-5 (S)-2-(4-Azido-2,3,5,6-tetrafluoro-benzoylamino)-6-[5-((3aR,6S,6aS)-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-hexanoic acid 2,5-dioxo-pyrrolidin-1-yl ester 

Relevant articles and documents

Design and synthesis of a highly efficient labelling reagent for incorporation of tetrafluorinated aromatic azide into proteins

Chemical labelling can significantly extend the structures and functions of proteins for advanced applications. Herein, a highly efficient bench-stable reagent diazo-azide was designed and synthesized for the incorporation of tetrafluorinated aromatic azi

A Potent Halogen-Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis

The covalent attachment of electron deficient perfluoroaryl substituents to a bis-iodotriazole pyridinium group produces a remarkably potent halogen bonding donor motif for anion recognition in aqueous media. Such a motif also establishes halogen bonding anion templation as a highly efficient method for constructing a mechanically interlocked molecule in unprecedented near quantitative yield. The resulting bis-perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by a factor of at least three orders of magnitude greater in comparison to a hydrogen bonding rotaxane host analogue. These observations further champion and advance halogen bonding as a powerful tool for recognizing anions in aqueous media.

Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction

We report a fast Staudinger reaction between perfluoroaryl azides (PFAAs) and aryl phosphines, which occurs readily under ambient conditions. A rate constant as high as 18 m?1 s?1 was obtained between methyl 4-azido-2,3,5,6-tetrafluorobenzoate and methyl 2-(diphenylphosphanyl)benzoate in CD3CN/D2O. Furthermore, the iminophosphorane product was stable toward hydrolysis and aza-phosphonium ylide reactions. This PFAA Staudinger reaction proved to be an excellent bioothorgonal reaction. PFAA-derivatized mannosamine and galactosamine were successfully transformed into cell-surface glycans and efficiently labeled with phosphine-derivatized fluorophore-conjugated bovine serum albumin.