58696-10-9

Basic information

• Product Name: Benzaldehyde, alpha-nitroso- (9CI)
• Synonyms: Benzaldehyde, alpha-nitroso- (9CI)
• CAS NO: 58696-10-9
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.1201
• Product Categories: AMIDE
• Mol File: 58696-10-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzaldehyde, alpha-nitroso- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, alpha-nitroso- (9CI)(58696-10-9)
• EPA Substance Registry System: Benzaldehyde, alpha-nitroso- (9CI)(58696-10-9)

Safety Data

• Hazardous Substances Data: 58696-10-9(Hazardous Substances Data)

Upstream product

• 495-18-1 Benzohydroxamic acid 
• 873-67-6 benzonitrile oxide 
• 20594-92-7 3,5-diphenyl-1,2,4-oxadiazole-4-oxide 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 97957-92-1 8α,5α-(N-benzoylepoxyimino)-5,8-dihydroergosterol acetate 
• 94936-52-4 methyl 3-benzoyl-2-oxa-3,5-diazabicyclo<2.2.2>oct-7-ene-5-carboxylate 
• 95687-88-0 (1S,5R)-6-Oxa-7-aza-bicyclo[3.2.2]non-8-en-7-yl-phenyl-methanone 
• 92011-99-9 methyl N-benzoyl-3-aza-2-oxabicyclo<2.2.2>oct-5-ene-5-carboxylate 
• 92011-98-8 methyl N-benzoyl-3-aza-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate 
• 130114-74-8 (4aS,8aR)-3-Phenyl-8,8a-dihydro-4aH-pyrido[4,3-e][1,4,2]dioxazine-7-carboxylic acid benzyl ester 
• 92011-94-4 N-benzoyl-3-aza-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxabicyclo<2.2.2>oct-5-ene 
• 92011-95-5 N-benzoyl-3-aza-5-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxabicyclo<2.2.2>oct-5-ene 
• 59438-62-9 3-benzoyl-2-oxa-3-azabicyclo<2.2.1>hept-5-ene 
• 1696-17-9 N,N-diethylbenzamide 
• 114217-83-3 methyl 7,8-diacetoxy-3-benzoyl-2-oxa-3,5-diazabicyclo<2.2.2>octane-5-carboxylate 
• 114217-91-3 2,3,4-tri-O-acetyl-N¹-benzoyl-5-deoxy-5-methoxycarbonylamino-α-DL-lyxopyranosylamine 
• 130114-76-0 (4aR,5R,6R,8aS)-5,6-Dihydroxy-3-phenyl-5,6,8,8a-tetrahydro-4aH-pyrido[4,3-e][1,4,2]dioxazine-7-carboxylic acid benzyl ester 

Relevant articles and documents

A mild oxidation method of hydroxamic acids: Efficient trapping of acyl nitroso intermediates

Ruthenium(II)-pyridine-2,6-dicarboxylate (pydic) of 2,6-bis(oxazolinyl)pyridine (pybox-dh) complex catalyzed the hydrogen peroxide oxidation of hydroxamic acid in the presence of cyclopentadiene to give acyl nitroso cycloadducts in 74-99% yield.

Photogeneration and reactivity of acyl nitroso compounds

Acyl nitroso compounds have been generated by photolysis of several different classes of precursors including 9,10-dimethylanthracene adducts, nitrodiazo compounds, and 1,2,4-oxadiazole-4-oxides. Consideration of the nitronate-like resonance structure of nitrodiazo compounds led to an examination of the photochemistry of nitronates with -leaving groups. Photolysis of such nitronates has been shown to generate an acyl nitroso species along with a carbene intermediate. Nanosecond time-resolved infrared (TRIR) spectroscopy has been used to detect photogenerated acyl nitroso compounds directly and to examine their reaction kinetics with amines and thiols. The mechanism of acyl nitroso aminolysis by primary amines involves general base catalysis, while the mechanism of aminolysis by secondary amines is strictly bimolecular. Thiols do not seem to be reactive with acyl nitroso compounds on the microsecond time scale, but thiolates are quite reactive. The reaction between benzoyl nitroside and an organic-soluble thiolate, tetrabutylammonium dodecanethiolate, proceeds via a proposed tetrahedral intermediate, which is observable by TRIR spectroscopy.

Direct observation of an Acyl nitroso species in solution by time-resolved IR spectrocopy

Benzoyl nitroside (5) was generated in solution by laser photolysis of 3,5-diphenyl-1,2,4-oxadiazole-4-oxide (4) and studied by time-resolved infrared spectroscopy. The second-order rate constantsfor reaction of 5 with diethylamine and 1,3-cyclohexadiene were determined to be (1.3 ± 0.5) × 105 M-1 s-1 and (6.0 ± 0.5) × 103 M-1 s-1, respectively. The formation of nitroxyl (HNO), a product of the reaction of 5 with diethylamine, was also observed. Copyright