72229-75-5

Basic information

• Product Name: N-methylphenylacetohydroxamic acid
• Synonyms: N-methylphenylacetohydroxamic acid
• CAS NO: 72229-75-5
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 0
• Mol File: 72229-75-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 300.4°C at 760 mmHg
• Flash Point: 135.5°C
• Appearance: /
• Density: 1.174g/cm³
• Vapor Pressure: 0.000499mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: N-methylphenylacetohydroxamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylphenylacetohydroxamic acid(72229-75-5)
• EPA Substance Registry System: N-methylphenylacetohydroxamic acid(72229-75-5)

Safety Data

• Hazardous Substances Data: 72229-75-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11NO2/c1-10(12)9(11)7-8-5-3-2-4-6-8/h2-6,12H,7H2,1H3

Upstream product

• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 103-80-0 phenylacetyl chloride 
• 103-82-2 phenylacetic acid 

Downstream Products

• 156025-71-7 N-(triflyloxy)-N-methylphenylacetamide 
• 63820-45-1 N-methyl-O-benzylphenylacetohydroxamic acid 
• 78899-96-4 N-methyl-2-chloro-2-phenylethanamide 
• 142437-76-1 N-(Mesyloxy)-N-methylphenylacetanilide 
• 148731-34-4 N-(((4-methylphenyl)sulfonyl)oxy)-N-methylphenylacetamide 
• 148731-35-5 N-(((4-bromophenyl)sulfonyl)oxy)-N-methylphenylacetamide 
• 148731-37-7 N-(((4-nitrophenyl)sulfonyl)oxy)-N-methylphenylacetamide 
• 121726-59-8 N-phenylacetyl-O-acetyl-N-methylhydroxylamine 
• 137283-41-1 C₁₇H₁₈N₂O₃ 
• 156183-26-5 N,O-diphenylacetyl-N-methylhydroxylamine 
• 203636-01-5 N-(4-Nitrobenzoyloxy)-N-methyl-2-phenylacetamide 
• 279242-97-6 N-Pivaloyloxy-N-methyl-2-phenylacetamide 
• 77130-13-3 N-Methylthiophenylacetamide 
• 65645-88-7 N-methyl-2-hydroxy-2-phenylethanamide 

Relevant articles and documents

Thoination of N-alkyl-O-acyl hydroxamic acid derivatives via Lawesson's reagent

N-alkyl-O-acyl thiohydroxamic acid derivatives were prepared in good yields by the treatment of their parent hydroxamic acids with Lawesson's reagent. Some of these thiohydroxamic acid derivatives exhibit the ability to undergo rearrangement under basic c

Base-promoted aromatic [3,3] sigmatropic rearrangement of N-acyl-O-arylhydroxylamine derivatives

The base-promoted aromatic [3,3] sigmatropic rearrangement of N-acyl-O-arylhydroxylamines giving α-(2-hydroxyphenyl)amides was successfully demonstrated. The substrates were prepared from N-substituted hydroxylamines by N-acylation followed by copper(I)-mediated O-arylation with boronic acids. Treatment of the substrates with lithium hexamethyldisilazide (LiHMDS) in THF at 0 °C to room temperature generated the corresponding amide enolates. The aromatic [3,3] rearrangement of the enolates provided the desired products in moderate to good yields. A crossover experiment produced only intramolecular products and clarified that the reaction proceeds via the aromatic [3,3] sigmatropic rearrangement, not a bond-cleavage–recombination process. Our method is a formal α-arylation of amides.

Base catalysed rearrangement of N-alkyl-O-acyl hydroxamic acids: Synthesis of 2-acyloxyamides

Activated N-alkyl-O-acyl hydroxamic acid derivatives 21a-t undergo thermal and base catalysed rearrangement to give 2-acyloxyamides 22a-t in good to excellent yields (50-100%). A range of inorganic and organic bases were screened for their efficiency in mediating the rearrangement 21 to 22, however, simple organic bases such as Et3N were found to be the most efficient. Both aromatic and aliphatic derived O-acyl groups were tolerated in the reaction. The electronic nature of the O-acyl group was found to effect the rate of the rearrangement with electron withdrawing groups (211 and 21o) increasing the observed rate and electron donating groups (21m and 21n) decreasing the observed rate. Cross-over experiments with 21a and 21h indicated a mechanism involving the intermediacy of free acyloxy anions. The requirement of a readily enolisable proton adjacent to the carbonyl group of the amide was found to be neccessary for the rearrangement as 21r and 21t both failed to rearrange under the reaction conditions investigated.