6048-20-0

Basic information

• Product Name: 4-nitrobenzoyl cyanide
• Synonyms: 4-nitrobenzoyl cyanide
• CAS NO: 6048-20-0
• Molecular Weight: 176.131
• Mol File: 6048-20-0.mol

Chemical Properties

• CAS DataBase Reference: 4-nitrobenzoyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-nitrobenzoyl cyanide(6048-20-0)
• EPA Substance Registry System: 4-nitrobenzoyl cyanide(6048-20-0)

Safety Data

• Hazardous Substances Data: 6048-20-0(Hazardous Substances Data)

Upstream product

• 825-52-5 2-(hydroxyimino)-2-phenylacetonitrile 
• 51920-53-7 p-nitrobenzoyl cyanide oxime 
• 71189-80-5 2-(4-nitrophenyl)-2-[(trimethylsilyl)oxy]acetonitrile 
• 3041-40-5 2-phenylmalononitrile 
• 1904-60-5 3-amino-2-phenylquinazolin-4(3H)-one 
• 99-81-0 4-Nitrophenacyl bromide 
• 74772-59-1 2-benzyl-3-amino-4-oxo-3,4-dihydroquinazoline 
• 1704-56-9 silver phenylcyanomethylenenitronate 
• 76-83-5 trityl chloride 
• 613-90-1 benzoyl cyanide 
• 7697-37-2 nitric acid 
• 7622-07-3 2,4-dinitrophenyl p-nitrobenzoate 
• 57-12-5 cyanide^(1-) 
• 1037-31-6 4-nitrophenyl 4-nitrobenzoate 

Downstream Products

• 6750-99-8 ethyl (4-nitrobenzoyl)cyanoacetate 
• 39718-99-5 N-anilino-4-nitrobenzamide 
• 63272-44-6 4-chloro-5-(4-nitro-phenyl)-2-phenyl-oxazole 
• 63272-46-8 4-bromo-5-(4-nitro-phenyl)-2-phenyl-oxazole 
• 134304-73-7 (E)-1-(4-nitrophenyl)-2-(oxazolidin-2-ylidene)ethanone 
• 134304-72-6 (E)-2-(4'-Nitrobenzoylmethylene)thiazolidine 
• 3769-90-2 2-(4'-Nitrobenzoylmethyl)pyridine 
• 134304-65-7 (Z)-2-(2'-Hydroxy-2'-(4-nitrophenyl)vinyl)pyridine 
• 134304-74-8 (E)-2-(1'-(4-Nitrobenzoyl)ethyliden)oxazolidine 
• 134304-61-3 (Z)-1,2-Dihydro-2-(4'-nitrobenzoylmethylene)quinoline 
• 134304-63-5 (Z)-1,2-Dihydro-1-(4'-nitrobenzoylmethylene)isoquinoline 
• 134304-71-5 (E)-2-(4'-Nitrobenzoylmethylene)benzoxazoline 
• 134304-75-9 2-(4'-Nitrobenzoylmethyl)benzoxazole 
• 66838-68-4 2-(4'-Nitrobenzoylmethyl)benzothiazole 

Relevant articles and documents

Acceptorless and Base-free Dehydrogenation of Cyanohydrin with (η6-Arene)halide(Bidentate Phosphine)ruthenium(II) Complex

Ruthenium-catalyzed dehydrogenation of cyanohydrins under acceptorless and base-free conditions was demonstrated for the first time in the synthesis of acyl cyanide. As opposed to the thermodynamically preferred elimination of hydrogen cyanide, the dehydrogenation of cyanohydrins could be kinetically controlled with ruthenium (II) bidentate phosphine complexes. The effects of the arene, phosphine ligands and counter anions were investigated in regard to catalytic activity and selectivity. Selective dehydrogenation can occur via β-hydride elimination with the experimentally observed [(alkoxide)Ru] complex. (Figure presented.).

Preparation method for D, L-phenylglycine and analogue thereof

The invention provides a preparation method for D, L-phenylglycine and an analogue thereof. According to the method, benzaldehyde, an analogue thereof and hydrocyanic acid are adopted as raw materials and subjected to cyanidation reaction, and then 2-hydroxy-benzyl cyanide or 2-hydroxy-benzyl cyanide analogue (cyanohydrin for short) is generated. Cyanohydrin reacts with carbon dioxide and the aqueous solution of ammonia, and then 5-phenyl-hydantoin and an analogue thereof (hydantoin for short) are generated. hydantoin is successively subjected to steam stripping, alkaline hydrolysis, steam stripping, decolorization, neutralization, crystallization, washing, centrifuging, drying and the like to obtain D, L-phenylglycine and the analogue thereof. Compared with the prior art, the preparation method for D, L-phenylglycine and the analogue thereof can significantly and effectively reduce the pollution, and fewer inorganic salt by-products are generated. Meanwhile, the prepared D, L-phenylglycine and the analogue thereof are high in product yield and high in purity. Counted in benzaldehyde and the analogue thereof, the yield of D, L-phenylglycine and the analogue thereof is larger than or equal to 96%, and the product purity is larger than or equal to 99%. Meanwhile, the process flow is simple and feasible, so that the method is worthy of market popularization and application.

HYDROXAMIC ACID DERIVATIVES

The disclosure includes hydroxamic compounds of Formula I: (I) wherein P, Z, and m are defined herein. Also disclosed is a method for treating a neoplastic disease or an immune disease with these compounds.

Structure-reactivity correlations in nucleophilic substitution reactions of Y-substituted phenyl X-substituted benzoates with anionic and neutral nucleophiles

A kinetic study is reported for the reactions of 4-nitrophenyl X-substituted benzoates (1a-l) and Y-substituted phenyl benzoates (2a-l) with two anionic nucleophiles (OH- and CN-) and three amines (piperidine, hydrazine, and glycylglycine) in 80 mol% H2O-20 mol% dimethyl sulfoxide (DMSO) at 25.0 ± 0.1 °C. Each Hammett plot exhibits two intersecting straight lines for the reactions of 1a-l with the anionic nucleophiles and piperidine, while the Yukawa-Tsuno plots for the same reactions are linear. The Hammett plots for the reactions of 2a-l with hydrazine and glycylglycine demonstrate much better linear correlations with σ- constants than with σ° or σ constants, indicating that the leaving group departure occurs at the rate determining step (RDS). On the contrary, σ- constants result in poorer Hammett correlation than σ° constants for the corresponding reactions with OH- and CN-, indicating that the leaving group departure occurs after the RDS for the reactions with the anionic nucleophiles. The large ρX value (1.7 ± 0.1) obtained for the reactions of 1a-l with the anionic nucleophiles supports the proposal that the reactions proceed through an addition intermediate with its formation being the RDS. The Royal Society of Chemistry 2006.

Reinterpretation of curved hammett plots in reaction of nucleophiles with aryl benzoates: Change in rate-determining step or mechanism versus ground-state stabilization

A kinetic study is reported for the reaction of the anionic nucleophiles OH-, CN-, and N3- with aryl benzoates containing substituents on the benzoyl as well as the aryloxy moiety, in 80 mol % H2O-20 mol % dimethyl sulfoxide at 25.0 °C. Hammett log k vs σ plots for these systems are consistently nonlinear. However, a possible traditional explanation in terms of a mechanism involving a tetrahedral intermediate with curvature resulting from a change in rate-determining step is considered but rejected. The proposed explanation involves ground-state stabilization through resonance interaction between the benzoyl substituent and the electrophilic carbonyl center in the two-stage mechanism. Accordingly, the data are nicely accommodated on the basis of the Yukawa-Tsuno equation, which gives linear plots for all three nuceophiles. Literature reports of the mechanism of acyl transfer processes are reconsidered in this light.

Anomalous Reaction of Arylmalononitriles with Nitric Acid. Para-Directing Nature of Dicyanomethyl Group and a Through-Ring Nitro/aci-Nitro Tautomerism of 4-Nitrophenylmalononitrile

Phenylmalononitrile reacts with nitric acid in dichloromethane at room temperature to afford 1,2-bis(4-nitrophenyl)-1,1,2,2-tetracyanoethane as an initial product, which readily suffers oxidative cleavage to give 4-nitrobenzoyl cyanide.Contrary to common

Triphenylmethyl Phenylcyanomethylenenitronate: Formation and Thermolysis

The previously reported formation of carbon dioxide, α,α'-bis(tritylazo)stilbene (4), benzonitrile N-oxide (5), trityl isocyanate (6), and C33H25N3O (11) from a mixture ot trityl chloride and silver phenylcyanomethylenenitronate in toluene is now attributed to the initial formation at -20 deg C of trityl phenylcyanomethylenenitronate (3) and its dissociations at 5 deg C.The ester (3) was characterized by conversion into bromonitrophenylacetonitrile (7) by treatment with bromine, to p-nitrobenzoyl cyanide (8) by treatment with dinitrogen tetraoxide, to trityl alcohol by hydrolysis, and to a mixture of trityl alcohol and trityl peroxide by exposure to the atmosphere.The bisazostilbene (4) (18percent) and C33H25N3O, identified by X-ray crystallographic analysis to be 4,5-diphenyl-1-triphenylmethoxy-1,2,3-triazole (11) (24percent), were obtained from the nitronate ester (3) in toluene at 5 deg C; the nitrile oxide (5) and the isocyanate (6) were obtained in low yields from the ester (3) in dimethyl sulphoxide at 25 deg C.Hydrolysis converted the triazole (11) into 1-hydroxy-4,5-diphenyl-1,2,3-triazole (12) and trityl alcohol.Silver p-bromophenylcyanomethylenenitronate and trityl chloride afforded α,α'-bis-(tritylazo)-p,p'-dibromostilbene and its thermolysis product, p,p'-dibromodiphenylacetylene.Fragmentation of the ester (3) in presence of added phenyl isocyanate gave the bisazo compound (4) and 3,4-diphenyl-1,2,4-oxodiazol-5-one (18).A similar mixture stored at -20 deg C gave the triazole (11) and the oxadiazolone (18).Aroyl nitrile oxides as well as phenyl isocyanate suppressed the formation of the red bisazostilbene (4).The intermediacy of the N-trityl imine (14) of 4H-3-phenyl-1,2-oxazet-4-one-2-oxide in the thermolysis of the nitronate (3) was discussed.

On the Preparation of Acyl Cyanides from Aldehydes

The O-silylated cyanohydrins 3 prepared from the aldehydes 1 with trimethylsilyl cyanide are oxidized photochemically or thermally with N-bromosuccinimide to afford the acyl cyanides 4a-n.Scope and limitations of the procedure are discussed.