4099-51-8

Basic information

• Product Name: N-hydroxy-2,2-diphenyl-acetamide
• Synonyms: N-hydroxy-2,2-diphenyl-acetamide;Diphenylacetohydroxamic acid;N-Hydroxy diphenylacetamide
• CAS NO: 4099-51-8
• Molecular Formula: C₁₄H₁₃NO₂
• Molecular Weight: 227.2585
• Mol File: 4099-51-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 172 °C(Solv: ethyl acetate (141-78-6))
• Appearance: off-white to light tan/
• Density: 1.199 g/cm³
• Refractive Index: 1.605
• Storage Temp.: 2-8°C
• Solubility: DMSO: >20mg/mL
• PKA: 9.01±0.40(Predicted)
• CAS DataBase Reference: N-hydroxy-2,2-diphenyl-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-2,2-diphenyl-acetamide(4099-51-8)
• EPA Substance Registry System: N-hydroxy-2,2-diphenyl-acetamide(4099-51-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 4099-51-8(Hazardous Substances Data)

Usage

General Description

N-hydroxy-2,2-diphenyl-acetamide is a chemical compound that is often used as an intermediate in the synthesis of pharmaceuticals and organic compounds. It is classified as an amide and contains a hydroxyl group attached to the nitrogen atom. This chemical has been found to exhibit potential antitumor and antioxidant properties, making it a promising candidate for further research and development. Additionally, N-hydroxy-2,2-diphenyl-acetamide has been studied for its potential use as a corrosion inhibitor in various industrial applications. Overall, this compound has shown diverse potential applications and is of interest for its unique chemical properties.

InChI:InChI=1/C14H13NO2/c16-14(15-17)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13,17H,(H,15,16)

Upstream product

• 4467-90-7 N-hydroxy-2,2-diphenylacetimidoyl chloride 
• 3469-00-9 methyl 2,2-diphenylacetate 
• 80928-23-0 2,2-diphenylacetylimidazole (1-((2,2-diphenyl)acetyl)imidazole) 
• 71-43-2 benzene 
• 60-29-7 diethyl ether 
• 7803-49-8 hydroxylamine 
• 141-78-6 ethyl acetate 
• 525-06-4 diphenyl ketene 
• 3468-99-3 ethyl diphenylacetate 
• 1871-76-7 diphenylacetic acid chloride 
• 117-34-0 2,2-diphenylacetic acid 
• 102-96-5 (2-nitroethenyl)benzene 
• 5153-67-3 nitrostyrene 

Downstream Products

• 6744-66-7 O-acetyl-N-diphenylacetyl-hydroxylamine 
• 88008-36-0 Ni((C₆H₅)2CHCONHO)(OOCCH₂NH₂) 
• 88033-25-4 Hg((C₆H₅)2CHCONHO)2 
• 71453-55-9 Co((C₆H₅)2CHCONHO)2 
• 22815-70-9 allyl benzhydrylcarbamate 
• 21420-61-1 N-(tert-butoxycarbonyl)(diphenylmethyl)amine 
• 91-00-9 Benzhydrylamine 
• 71453-56-0 Mn((C₆H₅)2CHCONHO)2 
• 71615-77-5 Ni((C₆H₅)2CHCONHO)2 
• 858220-00-5 O-benzoyl-N-diphenylacetyl-hydroxylamine 

Relevant articles and documents

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

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.

Carbonyldiimidazole-mediated lossen rearrangement

[Chemical Equation Presented] Carbonyldiimidazole (CDI) was found to mediate the Lossen rearrangement of various hydroxamic acids to isocyanates. This process is experimentally simple and mild, with imidazole and CO 2 being the sole stoichiometric byproduct. Significant for large-scale application, the method avoids the use of hazardous reagents and thus represents a green alternative to standard processing conditions for the Curtius and Hofmann rearrangements.