128396-72-5

Basic information

• Product Name: Alanine, N-(2-hydroxybenzoyl)-2-methyl-
• Synonyms: Alanine, N-(2-hydroxybenzoyl)-2-methyl-
• CAS NO: 128396-72-5
• Molecular Formula: C₁₁H₁₃NO₄
• Molecular Weight: 0
• Mol File: 128396-72-5.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Alanine, N-(2-hydroxybenzoyl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Alanine, N-(2-hydroxybenzoyl)-2-methyl-(128396-72-5)
• EPA Substance Registry System: Alanine, N-(2-hydroxybenzoyl)-2-methyl-(128396-72-5)

Safety Data

• Hazardous Substances Data: 128396-72-5(Hazardous Substances Data)

Upstream product

• 57224-51-8 N-benzoyl-2-methylalanine 
• 192046-36-9 2-hydroxy-N-[1-methyl-1-(N-methyl-N-phenylcarbamoyl)ethyl]benzamide 
• 98-88-4 benzoyl chloride 
• 128396-71-4 (OC₆H₄C(O)NHC(CH₃)2CO₂)Cu 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 208121-81-7 2-(2-methoxybenzoyl)-amino-2-methylpropionic acid 
• 208121-60-2 2-(2-methoxybenzoyl)-amino-2-methylpropionic acid methyl ester 

Downstream Products

• 192046-41-6 2-Hydroxy-N-{1-methyl-1-[1-methyl-1-(methyl-phenyl-carbamoyl)-ethylcarbamoyl]-ethyl}-benzamide 
• 192046-42-7 2-Hydroxy-N-{1-methyl-1-[1-(methyl-phenyl-carbamoyl)-cyclopentylcarbamoyl]-ethyl}-benzamide 
• 69-72-7 salicylic acid 

Relevant articles and documents

Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide

N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L1)(TMAO)2] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L1)2-, coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L=1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction.

Copper(II) mediated Aromatic Hydroxylation by Trimethylamine N-Oxide

Quantitative orthohydroxylation of N-benzoyl-2-methylalanine (1) occurs through its copper(II) salt oxidation by trimethylamine N-oxide; transitory formation of a Cu(III) species is proposed.