63760-17-8

Basic information

• Product Name: 4-[(4-METHOXYBENZYL)AMINO]PHENOL
• Synonyms: 4-[(4-METHOXYBENZYL)AMINO]PHENOL;phenol, 4-[[(4-methoxyphenyl)methyl]amino]-;4-(p-methoxybenzylamino)phenol
• CAS NO: 63760-17-8
• Molecular Formula: C₁₄H₁₅NO₂
• Molecular Weight: 229.27
• Mol File: 63760-17-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-[(4-METHOXYBENZYL)AMINO]PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4-METHOXYBENZYL)AMINO]PHENOL(63760-17-8)
• EPA Substance Registry System: 4-[(4-METHOXYBENZYL)AMINO]PHENOL(63760-17-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 63760-17-8(Hazardous Substances Data)

Upstream product

• 67097-24-9 4-[(4-methoxybenzylidene)amino]phenol 
• 123-11-5 4-methoxy-benzaldehyde 
• 123-30-8 4-amino-phenol 

Downstream Products

• 1169411-61-3 ethyl 1-(4-methoxybenzyl)-2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carboxylate 
• 1613063-37-8 2-cyano-N-(4-hydroxyphenyl)-N-(4-methoxybenzyl)acetamide 
• 1613063-69-6 1-(4-methoxybenzyl)-2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitrile 
• 1169411-31-7 ethyl 3-((4-hydroxyphenyl)(4-methoxybenzyl)amino)-3-oxopropanoate 

Relevant articles and documents

Versatile synthesis of 4-spiro-β-lactam-3-carbonitriles via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides

A series of 4-spiro-cyclohexadienonyl-β-lactam-3-carbonitriles, 2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitriles, was synthesized in satisfactory to excellent yields via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides with iodobenzene diacetate (IBD) as oxidant and potassium hydroxide as base. Acetic 4-spiro-cyclohexadienonyl- β-lactam-3-carbimidic anhydrides were obtained when organic base triethylamine was applied instead of potassium hydroxide. The mechanisms of the intramolecular nucleophilic cyclization and formation of acetic β-lactam-3-carbimidic anhydrides were proposed. The cyclization is a sequence of nucleophilic ipso addition and oxidative dearomatization. The formation of acetic carbimidic anhydrides is an acid-catalyzed acetate addition to the nitriles.

Enhancement of antioxidant activity of p-alkylaminophenols by alkyl chain elongation

The initial finding that the p-methylaminophenol (6) exhibited antioxidant activity led us to investigate whether the length of alkyl chains linked to the aminophenol residue might affect antioxidative activity. Therefore, we synthesized p-butylaminophenol (5), p-hexylaminophenol (4), p-octylaminophenol (3), and p-methoxybenzylaminophenol (7). All p-alkylaminophenols quenched α,α-diphenyl-β-picrylhydrazyl (DPPH) radicals, with 7 being the most potent DPPH radical scavenger. Lipid peroxidation by rat liver microsomes was reduced by p-alkylaminophenols in dose- and aminophenol alkyl chain length-dependent fashion (3>4>5>6), with 3 being the most potent lipid peroxidation inhibitor, at approximately 350-fold higher potency than 6. These results indicate that elongation of alkyl chains in p-alkylaminophenols may increase antioxidative activity, and that p-alkylaminophenols may potentially be useful in the development of antioxidants.