1266134-54-6

Basic information

• Product Name: 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate
• Synonyms: 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate;2-Azido-4,5-dihydro-1,3-dimethyl-1H-imidazolium hexafluorophosphate;2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate - A6170;2-azido-1,3-dimethyl-4,5-dihydroimidazol-1-ium:hexafluorophosphate
• CAS NO: 1266134-54-6
• Molecular Formula: C₅H₁₀N₅*F₆P
• Molecular Weight: 285.1305802
• Mol File: 1266134-54-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 205-210°C
• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate(1266134-54-6)
• EPA Substance Registry System: 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate(1266134-54-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 1266134-54-6(Hazardous Substances Data)

Usage

Description

2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate is a chemical compound that serves as an efficient diazo transfer reagent. It is used for the preparation of azides from primary amines and is considered an alternative to tosyl azide due to its easier-to-separate water-soluble by-product.

Uses

Used in Chemical Synthesis:
2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate is used as an efficient diazo transfer reagent for the preparation of azides from primary amines. This application is particularly useful in chemical synthesis processes where azides are required as intermediates or final products.
Used as an Alternative to Tosyl Azide:
In the chemical industry, 2-Azido-1,3-diMethyliMidazoliniuM Hexafluorophosphate is used as an alternative to tosyl azide. This is because it offers an easier-to-separate water-soluble by-product, which simplifies the purification process and reduces the complexity of the overall synthesis.

Upstream product

• 80-73-9 1,3-dimethyl-2-imidazolidinone 
• 101385-69-7 2-chloro-1,3-dimethyl-2-imidazolinium hexafluorophosphate 

Downstream Products

• 6926-44-9 phenethyl azide 
• 592489-25-3 1,3-dimethyl-2-(phenethylimino)imidazolidine 
• 611-70-1 phenyl isopropyl ketone 
• 1309976-99-5 C₁₉H₂₁N₃O 
• 1309977-10-3 C₁₄H₁₉N₃O 
• 2142-68-9 1-(2-chlorophenyl)ethanone 
• 577-16-2 2-Methylacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1309977-13-6 C₁₃H₁₇N₃O 
• 98-86-2 acetophenone 
• 1309977-12-5 C₂₁H₂₃N₃O 
• 1309977-03-4 C₁₉H₂₀ClN₃O 
• 1309977-00-1 C₂₀H₂₃N₃O 

Relevant articles and documents

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

Synthesis of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP)

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Protecting-group-free one-pot synthesis of glycoconjugates directly from reducing sugars

The conversion of sugars into glycomimetics typically involves multiple protecting-group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high-yielding and stereoselective process is highly desirable. The combined use of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and the Cu-catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one-step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole-linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one-pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.