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

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

Downstream Products

• 202003-06-3 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carbonitrile 
• 106308-44-5 rufinamide 
• 106308-50-3 1-(2,6-difluorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid 
• 217448-86-7 methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 166196-11-8 CGP 47292 
• 1314172-35-4 2-chloro-6-benzylamino-9-[1-(2,6-difluorobenzyl)-1H-1,2,3-triazol-4-yl-methyl]purine 
• 1020717-77-4 1-[(2,6-difluorophenyl)methyl]-1H-1,2,3-triazole-4-carbonyl chloride 
• 1596118-87-4 4-acetyl-1-(2,6-difluorobenzyl)-5-methyl-1H-1,2,3-triazole 
• 1622071-44-6 benzotriazolyl-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 1622071-45-7 4-nitrophenyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 1622071-46-8 N-benzotriazolyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate 
• 1622071-43-5 N-succinimidyl 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.

Design and synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives via click reactions

The synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives at the 4-OH via click reactions is accomplished, and a total of 16 novel sinomenine double N-heterocyclic derivatives are obtained in 74%–95% yields. The C-ring is first transformed into a 1,2-diketone structure under the action of hydrochloric acid, and then reacted with o-phenylenediamine to obtain a C-ring quinoxaline-substituted structure. The 4-OH of sinomenine reacts with chloropropyne to give an alkynyl sinomenine, and then reacts with sodium azide and various benzyl chlorides to give the target compounds. All the synthesized derivatives are characterized by Fourier-transform infrared spectrometry, high resolution mass spectrometry, 1H NMR, and 13C NMR spectroscopy.

Organic synthesis in a modular robotic system driven by a chemical programming language

The synthesis of complex organic compounds is largely a manual process that is often incompletely documented. To address these shortcomings, we developed an abstraction that maps commonly reported methodological instructions into discrete steps amenable to automation. These unit operations were implemented in a modular robotic platform by using a chemical programming language that formalizes and controls the assembly of the molecules. We validated the concept by directing the automated system to synthesize three pharmaceutical compounds, diphenhydramine hydrochloride, rufinamide, and sildenafil, without any human intervention. Yields and purities of products and intermediates were comparable to or better than those achieved manually. The syntheses are captured as digital code that can be published, versioned, and transferred flexibly between platforms with no modification, thereby greatly enhancing reproducibility and reliable access to complex molecules.