946423-58-1

Basic information

• Product Name: 9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt
• Synonyms: 9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt;9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt (>90%)
• CAS NO: 946423-58-1
• Molecular Formula: C₂₆H₂₃NO₇S
• Molecular Weight: 493.52832
• Product Categories: Aromatics, Heterocycles, Labeling and Diagnostics Reagents, Sulfur & Selenium Compounds
• Mol File: 946423-58-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: 9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt(946423-58-1)
• EPA Substance Registry System: 9-[(4-Carboxy-2,6-diMethylphenoxy)carbonyl]-10-(3-sulfopropyl)acridiniuM Inner Salt(946423-58-1)

Safety Data

• Hazardous Substances Data: 946423-58-1(Hazardous Substances Data)

Upstream product

• 946423-59-2 2'-6'-dimethyl-4'-methoxycarbonylphenyl 10-sulfopropylacridinium-9-carboxylate 

Downstream Products

• 194357-64-7 NSP-DMAE-NHS ester 
• 1307864-42-1 C₃₆H₄₄N₄O₈S 
• 1307864-43-2 NSP-DMAE-ZCB-NHS 
• 1307864-26-1 C₃₆H₄₆N₄O₉S₂ 
• 1307864-27-2 C₄₁H₅₂N₄O₁₂S₂ 
• 1307864-28-3 NSP-DMAE-Z-NHS 
• 1307864-37-4 C₃₅H₄₄N₄O₉S₂ 
• 1307864-38-5 C₄₀H₅₀N₄O₁₂S₂ 
• 1307864-39-6 NSP-DMAE-Z₂-NHS 

Relevant articles and documents

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.