55383-76-1

Basic information

• Product Name: Propanenitrile, 3-[[(4-methoxyphenyl)methyl]amino]-
• CAS NO: 55383-76-1
• Molecular Formula: C11H14N2O
• Molecular Weight: 190.245
• Mol File: 55383-76-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Propanenitrile, 3-[[(4-methoxyphenyl)methyl]amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanenitrile, 3-[[(4-methoxyphenyl)methyl]amino]-(55383-76-1)
• EPA Substance Registry System: Propanenitrile, 3-[[(4-methoxyphenyl)methyl]amino]-(55383-76-1)

Safety Data

• Hazardous Substances Data: 55383-76-1(Hazardous Substances Data)

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 107-13-1 acrylonitrile 

Downstream Products

• 1036733-20-6 (S)-3-((4-methoxybenzyl)(4-(5-phenylpent-4-yn-2-yloxy)but-2-ynyl)amino)propanenitrile 
• 394211-31-5 N-(3-aminopropyl)-N-(4-aminobutyl)-4-methoxybenzylamine 
• 394211-26-8 N₁-(3-amino-propyl)-N₁-(3-methoxy-benzyl)-propane-1,3-diamine 
• 35303-28-7 1-(4-methoxy-benzyl)-aziridine-2-carbonitrile 
• 916759-34-7 C₁₁H₁₃ClN₂O 
• 394211-25-7 3-[(2-cyano-ethyl)-(4-methoxy-benzyl)-amino]-propionitrile 
• 394211-30-4 N-(2-cyanoethyl)-N-(3-cyanopropyl)-4-methoxybenzylamine 

Relevant articles and documents

Aza-Michael mono-addition using acidic alumina under solventless conditions

Aza-Michael reactions between primary aliphatic and aromatic amines and various Michael acceptors have been performed under environmentally-friendly solventless conditions using acidic alumina as a heterogeneous catalyst to selectively obtain the corresponding mono-adducts in high yields. Ethyl acrylate was the main acceptor used, although others such as acrylonitrile, methyl acrylate and acrylamide were also utilized successfully. Bi-functional amines also gave the mono-adducts in good to excellent yields. Such compounds can serve as intermediates for the synthesis of anti-cancer and antibiotic drugs.

Synthesis of acridine-based DNA bis-intercalating agents

Methods for the synthesis of N1, N8-bis(9-acridinyl)- N4-(4-hydroxybenzyl)-spermidine and N1, N 7-(hydroxybenzyl)-bis-(3-aminopropyl)amine were investigated. Thus monocyanoethylation of 4-methoxybenzylamine followed by treatment with 4-chlorobutyronitrile gave the dinitrile N-(2-cyanoethyl)-N-(3-cyanopropyl)-4- methoxy-benzylamine. Subsequent in situ reduction with lithium aluminium hydride gave the corresponding diamine. Biscyanoethylation of 4-methoxybenzylamine with 2 mole of acrylonitrile followed by reduction yielded the diamine N, N-bis-(3-aminopropyl)-4-methoxybenzylamine. Both diamines reacted smoothly with 9-methoxyacridine to give the bis-(9-acridinyl) compounds 11 and 15 but with 4,5-dimethyl-9-methoxyacridine, the bis compound 16 was produced in only low yields. Demethylation of the dinitriles by a variety of approaches all failed to give the corresponding hydroxybenzyl derivatives. These studies yielded useful methylated tyrosine derivatives which could also be iodinated. This study has been useful for elucidating chemical methods needed for the synthesis of the desired tyrosine-based bis acridine compound and for alerting us to the need to synthesise a more labile protected tyrosine intermediate which will be easily deprotected to afford the desired tyrosine-based bis acridine compound.