946423-59-2

Upstream product

• 1120-71-4 1,3-propanesultone 
• 1156506-80-7 2',6'-dimethyl-4'-methoxycarbonylphenyl acridine-9-carboxylate 
• 1536146-87-8 2'-6'-dimethyl-4'-methoxycarbonylphenyl acridan-9-carboxylate 

Downstream Products

• 946423-58-1 2',6'-dimethyl-4'-carboxyphenyl-10-sulfopropylacridinium-9-carboxylate 
• 1307864-44-3 C₃₁H₃₆N₃O₆S⁽¹⁺⁾ 
• 1307864-45-4 C₃₄H₄₂N₃O₉S₂⁽¹⁺⁾ 
• 1307864-50-1 C₃₇H₄₃N₄O₁₁S₂⁽¹⁺⁾ 
• 1307864-47-6 C₄₃H₆₃N₆O₁₁S₃⁽¹⁺⁾ 
• 1307864-49-8 CN-NSP-DM AE-Z₃-NHS 

Relevant academic research and scientific papers

SYNTHESIS OF ACRIDINIUM COMPOUNDS BY N-ALKYLATION OF ACRIDANS

A method is provided for N-alkylation of acridine compounds by reduction of acridines to corresponding acridans to improve the reactivity of the acridine nitrogen, and subsequent N-alkylation of the acridans in ionic liquid solvents to provide the corresp

Facile N-alkylation of acridine esters with 1,3-propane sultone in ionic liquids

Hydrophilic chemiluminescent acridinium esters containing N-sulfopropyl groups are extremely useful labels in the clinical diagnostics industry. The synthesis of these labels is normally accomplished by N-alkylation of the acridine ester precursors with the carcinogenic reagent 1,3-propane sultone in neat reactions where the alkylating reagent also serves as the solvent. Product yields are often poor, the reactions are not reproducible and are also difficult to scale-up. In our efforts to develop a greener and a more efficient synthesis of N-sulfopropyl acridinium esters, we have discovered that commonly used room temperature ionic liquids such as [BMIM][BF4] and [BMIM][PF 6] are excellent media for the N-alkylation of poorly reactive acridine esters with 1,3-propane sultone. Advantages include a significant reduction in the amount of toxic 1,3-propane sultone needed for good conversion to product, and minimal formation of polysulfonated products. The alkylation reaction in ionic liquids is amenable to scale-up for the synthesis of gram quantities of hydrophilic, chemiluminescent acridinium esters. The Royal Society of Chemistry.

FACILE N-ALKYLATION OF ACRIDINE COMPOUNDS IN IONIC LIQUIDS

A method is provided for N-alkylation of acridine compounds, typically with a 1,3- propane sultone alkylating reagent, in ionic liquid solvents to provide the corresponding acridinium compounds in high yeild.