6275-72-5

Usage

InChI:InChI=1/C9H10N2O4/c1-2-15-9(12)10-7-4-3-5-8(6-7)11(13)14/h3-6H,2H2,1H3,(H,10,12)

Upstream product

• 64-17-5 ethanol 
• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 15999-30-1 (3-nitro-phenyl)-carbonimidic acid dichloride 
• 33322-43-9 3-nitro-benzoic acid bromoamide 
• 141-52-6 sodium ethanolate 
• 645-09-0 3-nitrobenzamide 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 99-09-2 3-nitro-aniline 
• 618-94-0 3-nitrobenzoic acid hydrazide 
• 817-87-8 ethyl azidocarbonate 
• 98-95-3 nitrobenzene 
• 51028-37-6 (3-nitro-phenyl)-carbamoyl chloride 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 51028-37-6 (3-nitro-phenyl)-carbamoyl chloride 
• 17433-92-0 N-(3-nitrophenyl)hydrazinecarbamide 
• 1234-21-5 1,3-bis(3-nitrophenyl)urea 
• 122712-58-7 3-Amino-phenylcarbaminsaeureethylester-Hydrochlorid 
• 99-09-2 3-nitro-aniline 
• 75953-50-3 6-Amino-2-p-tolyl-2H-benzo[1,2,4]triazin-3-one 
• 75953-52-5 6-Amino-2-(4-chloro-phenyl)-2H-benzo[1,2,4]triazin-3-one 
• 75953-55-8 6-Amino-2-(4-methoxy-phenyl)-2H-benzo[1,2,4]triazin-3-one 
• 75953-48-9 6-Amino-2-phenyl-2H-benzo[1,2,4]triazin-3-one 
• 122137-19-3 (5-Amino-2-phenylazo-phenyl)-carbamic acid ethyl ester; hydrochloride 
• 105798-22-9 (5-Amino-2-phenylazo-phenyl)-carbamic acid ethyl ester 
• 105798-23-0 (5-Amino-2-p-tolylazo-phenyl)-carbamic acid ethyl ester 
• 105798-25-2 [5-Amino-2-(4-chloro-phenylazo)-phenyl]-carbamic acid ethyl ester 
• 105798-24-1 [5-Amino-2-(4-methoxy-phenylazo)-phenyl]-carbamic acid ethyl ester 

Relevant academic research and scientific papers

Reaction of organozinc halides with aryl isocyanates

Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.

Synthesis and fungicidal activity of some sulphide derivatives of O-ethyl-N-substituted phenylcarbamates

Monosulphides of O-ethyl-N-substituted phenylcarbamates were prepared by the reaction between O-ethyl-N-substituted phenylcarbamates and sulphur dichloride, while the corresponding disulphides were prepared by the reaction between O-ethyl-N-substituted ph

Electrophilic Aromatic N-Substitution by Ethoxycarbonylnitrenium Ion generated from Ethyl Azidoformate in the Presence of Trifluoroacetic Acid

Thermal reactions of ethyl azidoformate with aromatic compounds in the presence of trifluoroacetic acid (TFA) gave ethyl N-arylcarbamates.Toluene, nitrobenzene, or naphthalene was selectively attacked on the ortho- and para-positions, on the ortho- and meta-positions, or in the 1- and 2-positions, respectively.The yields were ca. twice as high as those for thermolysis ( a nitrene-azepine route) in the absence of TFA with the subsequent addition of TFA at room temperature.The positional selectivities for toluene and naphthalene were lower for the former thermolysis than for the latter.The reactivity of cyclohexane or toluene relative to benzene was greater in the latter thermolysis than the former.A Hammett plot with ρ - 1.7 was obtained for the formation of ethyl N-arylcarbamates in the former thermolysis in TFA-nitrobenzene (8:2 v/v); the value was more negative than that (-1.32) for the disappearance of substituted benzenes in the reaction with ethoxycarbonylnitrene.The results suggest that the thermolysis in the presence of TFA involves an electrophilic aromatic N-substitution by ethoxycarbonylnitrenium ion.

Electrophilic Aromatic Substitution by Ethoxycarbonylnitrenium Ion. Reactions of Ethyl Azidoformate with Aromatics in the Presence of Trifluoroacetic Acid

Electrophilic aromatic substitution by ethoxycarbonylnitrenium ion occurs in reactions of ethyl azidoformate with aromatics in the presence of trifluoroacetic acid, giving ethyl n-arylcarbamates.