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

Uses

Efficient diazo transfer reagent for the preparation of azides from primary amines. An alternative to tosyl azide with an easier-to-separate water soluble by-product.

Upstream product

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

Downstream Products

• 1309976-99-5 C₁₉H₂₁N₃O 
• 1309977-01-2 C₂₀H₂₃N₃O₂ 
• 1309977-09-0 C₂₂H₂₇N₃O 
• 1309977-10-3 C₁₄H₁₉N₃O 
• 1309977-04-5 C₁₉H₂₀BrN₃O 
• 1309977-08-9 C₂₃H₂₃N₃O 
• 1309977-02-3 C₂₁H₂₅N₃O₃ 
• 1309977-13-6 C₁₃H₁₇N₃O 
• 1309977-05-6 C₂₁H₂₃N₃O₃ 
• 1309977-00-1 C₂₀H₂₃N₃O 
• 1309977-03-4 C₁₉H₂₀ClN₃O 
• 1309977-12-5 C₂₁H₂₃N₃O 
• 6926-44-9 phenethyl azide 
• 592489-25-3 1,3-dimethyl-2-(phenethylimino)imidazolidine 

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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A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.