710311-79-8

Basic information

• Product Name: Benzamide, N-hydroxy-3,5-dimethoxy- (9CI)
• Synonyms: Benzamide, N-hydroxy-3,5-dimethoxy- (9CI)
• CAS NO: 710311-79-8
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.18794
• Product Categories: METHOXY
• Mol File: 710311-79-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 141-143 °C
• Appearance: /
• Density: 1.241±0.06 g/cm3(Predicted)
• PKA: 8.38±0.10(Predicted)
• CAS DataBase Reference: Benzamide, N-hydroxy-3,5-dimethoxy- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-hydroxy-3,5-dimethoxy- (9CI)(710311-79-8)
• EPA Substance Registry System: Benzamide, N-hydroxy-3,5-dimethoxy- (9CI)(710311-79-8)

Safety Data

• Hazardous Substances Data: 710311-79-8(Hazardous Substances Data)

Upstream product

• 17213-57-9 3,5-dimethoxybenzoyl chloride 
• 67333-75-9 1-(3,5-dimethoxy-benzoyl)-1H-imidazole 
• 1132-21-4 3,5-dimethoxybenzoic acid 

Downstream Products

• 1420471-39-1 allyl (3,5-dimethoxyphenyl)carbamate 
• 54132-76-2 3,5-dimethoxyphenyl isocyanate 
• 1427180-43-5 3,5-dimethoxy-N-(pivaloyloxy)benzamide 
• 1353562-24-9 N-(3,5-dimethoxyphenyl)formamide 
• 10272-07-8 3.5-dimethoxyaniline 

Relevant articles and documents

Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions

The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.

One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives

A one-pot synthesis of primary amines from carboxylic acids through a Lossen rearrangement of hydroxamic acid derivatives, which were in situ generated by the reaction of carboxylic acids with O-trimethylsilylhydroxylamine (NH2OTMS) and carbonyl diimidazole (CDI, 1.5 equiv) in dimethyl sulfoxide at room temperature, has been achieved. This one-pot method could be applied to various carboxylic acids such as aromatic, heteroaromatic, aliphatic, and optically active substrates.