31335-69-0

Basic information

• Product Name: N-hydroxy-N-phenylformamide
• Synonyms: formamide, N-hydroxy-N-phenyl-; N-Hydroxy-N-phenylformamide; N-Phenylformohydroxamic acid
• CAS NO: 31335-69-0
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.136
• Mol File: 31335-69-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 265.137°C at 760 mmHg
• Flash Point: 114.151°C
• Density: 1.297g/cm³
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.631
• CAS DataBase Reference: N-hydroxy-N-phenylformamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-N-phenylformamide(31335-69-0)
• EPA Substance Registry System: N-hydroxy-N-phenylformamide(31335-69-0)

Safety Data

• Hazardous Substances Data: 31335-69-0(Hazardous Substances Data)

Upstream product

• 64-18-6 formic acid 
• 100-65-2 N-Phenylhydroxylamine 
• 50-00-0 formaldehyd 
• 586-96-9 Nitrosobenzene 
• 865-47-4 potassium tert-butylate 
• 2706-75-4 sodium glyoxylate 
• 298-12-4 Glyoxilic acid 
• 5913-00-8 N-hydroxy-N,N'-diphenyl-formamidine 
• 7732-18-5 water 
• 62-53-3 aniline 
• 563-96-2 2,2-dihydroxyacetic acid 
• 98-95-3 nitrobenzene 
• 430-75-1 glyoxylate 
• 100-61-8 N-methylaniline 

Downstream Products

• 586-96-9 Nitrosobenzene 
• 58246-76-7 indole-1-carboxaldehyde 
• 936476-34-5 Zn(C(CH₃)2SCH(C₃HN₂(CH₃)2)2)(HCON(C₆H₅)O) 
• 103-71-9 phenyl isocyanate 
• 64-18-6 formic acid 
• 123-30-8 4-amino-phenol 
• 80820-91-3 N-Cyclohexylcarbamoyloxy-N-phenylformamid 
• 80820-92-4 N-(4-Nitrophenyl)carbamoyloxy-N-phenylformamid 
• 100-65-2 N-Phenylhydroxylamine 

Relevant articles and documents

Evidence for proton transfer from carbon to chloride ion in solution

Unambiguous evidence for proton transfer from carbon to chloride ion in solution has been obtained for the first time, in the formation of hydroxamic acids from aldehydes and nitrosobenzenes in acetonitrile.

Reactions of Carbonyl Group with Nitroso Compounds: Reaction of Formaldehyde with Substituted Nitrosobenzenes

Formaldehyde reacts with substituted nitrosobenzenes giving the corresponding N-phenylhydroxamic acids.A mechanism involving three sequential steps in this reaction is proposed.The first step is the nucleophilic attack of the nitroso group on the carbonyl group which leads to the formation of the unstable tetrahedral zwitterionic intermediate.This step followed by the proton transfer to the zwitterionic intermediate to form more stable nitrosocarbinolic cation intermediate, which in the subsequent step undergoes the rate-controlling elimination of proton from the C-atom of nitrosocarbinolic group, leading to the final product, hydroxamic acid.The first and the second step appear to be reversible.The experimental evidence obtained, which is the basis for such a description of the investigated reaction, includes: a) the order of reactivity of substituted nitrosobenzenes, as demonstrated by the plot of log kobs vs. ? Hammett parameters with slope of -1.74; b) the observation of a general-acid catalysis; c) the observation of the inverse solvent deuterium isotope effect of ca. 1.8 in the reaction; d) the observation of kinetic primary deuterium isotope effect of ca. 8 related to to the 'water' reactions of formaldehyde with substituted nitrosobenzenes; e) the observation of general-base catalysis in the reaction; f) the observation of the kinetic primary deuterium isotope effect of ca. 2.1 for the acetate-ion catalyzed reaction.

Reaction of Substituted Nitrosobenzenes with Formaldehyde

Substituted nitrosobenzenes react with formaldehyde in an acid-catalysed reaction giving N-phenylhydroxamic acids.

Intermediate analogue inhibitors of mandelate racemase: N-Hydroxyformanilide and cupferron

Mandelate racemase (MR) catalyzes the 1,1-proton transfer that interconverts the enantiomers of mandelate. The transition state/intermediate analogues N-hydroxyformanilide (Ki = 2.79 ± 0.19 μM) and cupferron (Ki = 2.67 ± 0.09 μM) are

Salt effects and kinetic isotope effects interconnected. Evidence for the involvement of chloride ion in the C-H bond breaking in aqueous solution?

An unusual change of the primary kinetic isotope effect in the formation of hydroxamic acid from nitrosobenzene and formaldehyde in mixed solvents on addition of very small quantities of salts and at higher salt concentration in water was observed and interpreted in terms of ion pairing and hydrogen bonding phenomena in the reaction.