106308-60-5

Basic information

• Product Name: 2,6-difluorobenzyl azide
• Synonyms: 2-(Azidomethyl)-1,3-difluorobenzene; 2,6-Difluorobenzyl azide; benzene, 2-(azidomethyl)-1,3-difluoro-
• CAS NO: 106308-60-5
• Molecular Formula: C₇H₅F₂N₃
• Molecular Weight: 169.1315
• Mol File: 106308-60-5.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: 2,6-difluorobenzyl azide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-difluorobenzyl azide(106308-60-5)
• EPA Substance Registry System: 2,6-difluorobenzyl azide(106308-60-5)

Safety Data

• Hazardous Substances Data: 106308-60-5(Hazardous Substances Data)

Usage

General Description

2,6-difluorobenzyl azide, also known as 2,6-difluorophenyl azide, is a chemical compound with the molecular formula C7H5FN3. It is commonly used in organic synthesis, particularly for the creation of aziridines, which can be used as building blocks for a variety of pharmaceutical and agrochemical products. Additionally, 2,6-difluorobenzyl azide is a versatile reagent in click chemistry reactions, where it is used to modify biomolecules and create new materials. It is important to handle this chemical with care, as azides are known to be potentially explosive and should be handled with caution.

Upstream product

• 443-84-5 2,6-difluorotoluene 
• 13671-00-6 methyl 2,6-difluorobenzoate 
• 13648-23-2 methyl 3,5-dichloro-2,4,6-trifluorobenzoate 
• 19064-18-7 2,6-difluorobenzyl alcohol 
• 697-73-4 2,6-difluorobenzyl chloride 
• 85118-00-9 2,6-Difluorobenzyl bromide 

Downstream Products

• 202003-06-3 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carbonitrile 
• 106308-44-5 rufinamide 
• 217448-86-7 methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 

Relevant articles and documents

From alcohol to 1,2,3-triazole: Via a multi-step continuous-flow synthesis of a rufinamide precursor

Rufinamide is an antiepileptic drug used to treat the Lennox-Gastaut syndrome. It comprises a relatively simple molecular structure. Rufinamide can be synthesized from an organohalide in three steps. Recently we have shown that microreactor flow networks have better sustainability profiles in terms of life-cycle assessment than the respective consecutive processing in a batch. The analysis was based on the results of a single step conversion from batch to continuous mode. An uninterrupted continuous process towards rufinamide was developed, starting from an alcohol precursor, which is converted to the corresponding chloride with hydrogen chloride gas. The chloride is then converted to the corresponding organoazide that yields the rufinamide precursor via cycloaddition to the greenest and cheapest dipolarophile available on the market. The current process demonstrates chemical and process-design intensification aspects encompassed by novel process windows. Single reaction steps are chemically intensified via a wide range of conditions available in a microreactor environment. Meanwhile, the connection of reaction steps and separations results in process-design intensification. With two in-line separations the process consists of five stages resulting in a total yield of 82% and productivity of 9 g h-1 (11.5 mol h-1 L-1). The process minimizes the isolation and handling of strong alkylating or energetic intermediates, while minimizing water and organic solvent consumption.

Hydrogen Bond Directed Photocatalytic Hydrodefluorination and Methods of Use Thereof

Methods of synthesizing compounds comprising fluorinated aryl groups are disclosed, wherein said methods utilize hydrogen bond directed photocatalytic hydrodefluorination.

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

Highly regioselective and sustainable solar click reaction: A new post-synthetic modified triazole organic polymer as a recyclable photocatalyst for regioselective azide-alkyne cycloaddition reaction

The synthesis of pharmaceutically active 1,2,3-triazoles has been continuously scrutinized in the search for unique and effective catalysts to make the process efficient, green, and sustainable. Here, we are presenting a new visible light active Ni(ii) cyclam-integrated triazole-linked organic polymer (Ni-TLOP) photocatalyst for the synthesis of 1,2,3-triazole compounds with excellent efficiency and regioselectivity. The reaction was studied for a series of substrates and the absolute regioselectivity of a representative triazole product has also been confirmed by X-ray crystallography. The proficiency and chemical orthogonality of the Ni-TLOP are remarkable and it shows enhanced efficiency and regioselectivity. The use of a recyclable photocatalyst and non-hazardous reagents makes the catalytic system sustainable and environmentally friendly. This photocatalyzed click reaction technique has been successfully applied to the expedient synthesis of one of the most sold anti-epileptic drugs rufinamide.