102185-28-4

Basic information

• Product Name: 4-AMINOPHENYLPHOSPHORYLCHOLINE
• Synonyms: 4-AMINOPHENYLPHOSPHORYLCHOLINE;p-aminophenylphosphorylcholine;4-Aminophenyl 2-(trimethylammonio)ethyl phosphate;2-[[(4-AMinophenoxy)hydroxyphosphinyl]oxy]-N,N,N-triMethyl-ethanaMiniuM;APPC *100 Mg* [4-AMinophenylphosphorylcholine];p-aminophenylphosphocholine;APPC [4-Aminophenylphosphorylcholine];Ethanaminium,2-[[(4-aminophenoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-, inner salt
• CAS NO: 102185-28-4
• Molecular Formula: C₁₁H₁₉N₂O₄P
• Molecular Weight: 310.71
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Amines;Aromatics;Miscellaneous Reagents
• Mol File: 102185-28-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 270-273
• Appearance: Off white powder
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly, Heated), Water (Slightly)
• Stability: Hygroscopic, Light Sensitive
• CAS DataBase Reference: 4-AMINOPHENYLPHOSPHORYLCHOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOPHENYLPHOSPHORYLCHOLINE(102185-28-4)
• EPA Substance Registry System: 4-AMINOPHENYLPHOSPHORYLCHOLINE(102185-28-4)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 102185-28-4(Hazardous Substances Data)

Usage

Chemical Properties

Off White Powder

Definition

ChEBI: A phosphocholine that is the 4-aminophenyl ester of choline phosphate.

InChI:InChI=1/C11H19N2O4P/c1-13(2,3)8-9-16-18(14,15)17-11-6-4-10(12)5-7-11/h4-7H,8-9,12H2,1-3H3

Synthetic route

p-nitrophenyl phosphorylcholine (21064-69-7) → p-aminophenylphosphorylcholine (102185-28-4)

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol for 0.0166667h;

1-dichlorophosphoryloxy-4-nitro-benzene (777-52-6) → p-aminophenylphosphorylcholine (102185-28-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) quinoline; 2.) IWT<*>TMD-8 ion exchange resin / 1.) acetonitrile, 0 deg C, 5 h; 2.) acetonitrile-pyridine-water 2: ammonium formate / 10percent Pd/C / methanol / 0.02 h View Scheme

choline iodide (17773-10-3) → p-aminophenylphosphorylcholine (102185-28-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) quinoline; 2.) IWT<*>TMD-8 ion exchange resin / 1.) acetonitrile, 0 deg C, 5 h; 2.) acetonitrile-pyridine-water 2: ammonium formate / 10percent Pd/C / methanol / 0.02 h View Scheme

4-(bromomethyl)benzo-15-crown-5 (74046-55-2) + p-aminophenylphosphorylcholine (102185-28-4) → 4-<(p-aminophenyl)phosphocholine> methyl benzo-15-crown-5

Conditions	Yield
With sodium hydrogencarbonate In methanol; butan-1-ol at 45℃; for 48h;	43 mg

p-aminophenylphosphorylcholine (102185-28-4) → p-diazophenylphosphorylcholine

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 20℃;

Upstream product

• 17773-10-3 choline iodide 
• 777-52-6 1-dichlorophosphoryloxy-4-nitro-benzene 
• 21064-69-7 p-nitrophenyl phosphorylcholine 

Downstream Products

• 61114-50-9 p-diazophenylphosphorylcholine 

Relevant articles and documents

Facile reduction in the synthesis of phosphorylcholine affinity columns

Reduction of p-nitrophenylphosphorylcholine to the amine utilizing ammonium formate and 10% Pd/C in methanol, followed by in situ generation of the diazonium salt resulted in the synthesis of p-diazophenylphosphorylcholine. This reaction was simpler than the usual approach utilizing hydrogen gas for the reduction to p-aminophenylphosphorylcholine. The diazonium salt then successfully reacted with the amino acid tyrosine, which had been previously attached to an agarose bead. Alternatively the diazonium salt was coupled to BSA and the resulting conjugate used to coat ELISA plates. Selective PC-binding antibodies recognized the antigen, and bound specifically to both the column and plates.