2137-92-0

Basic information

• Product Name: Thiocyanic acid 4-nitrophenyl ester
• Synonyms: Thiocyanic acid 4-nitrophenyl ester
• CAS NO: 2137-92-0
• Molecular Formula: C₇H₄N₂O₂S
• Molecular Weight: 180.1839
• Mol File: 2137-92-0.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 334.5°Cat760mmHg
• Flash Point: 156.1°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: Thiocyanic acid 4-nitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Thiocyanic acid 4-nitrophenyl ester(2137-92-0)
• EPA Substance Registry System: Thiocyanic acid 4-nitrophenyl ester(2137-92-0)

Safety Data

• Hazardous Substances Data: 2137-92-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H4N2O2S/c8-5-12-7-3-1-6(2-4-7)9(10)11/h1-4H

Upstream product

• 937-32-6 4-nitrobenzenesulfenyl chloride 
• 151-50-8 potassium cyanide 
• 5285-87-0 phenyl thiocyanate 
• 3321-93-5 4-iodo-phenyl thiocyanate 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 333-20-0 potassium thioacyanate 
• 74-90-8 hydrogen cyanide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 2942-58-7 diethyl cyanophosphonate 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 
• 1111-67-7 copper(I) thiocyanate 
• 100-01-6 4-nitro-aniline 
• 7697-37-2 nitric acid 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 100-32-3 di(p-nitrophenyl) disulfide 
• 2987-46-4 4-thiocyanatoaniline 
• 1594-56-5 2,4-dinitro-phenyl thiocyanate 
• 95062-77-4 S-(4-nitrophenyl) thiocarbamate 
• 60951-95-3 C₉H₁₀N₂O₃S 
• 701-57-5 1-methylthio-4-nitro-benzene 
• 111480-63-8 3-methyl-5-(4-nitrophenylthio)-1,2,4-oxadiazole 
• 102-07-8 bis(diphenyl)urea 
• 76665-92-4 p-nitrophenyl perfluoroisopropyl sulfide 
• 89333-93-7 3-(4-nitrophenyl)-5-(4-nitrophenylthio)-1,2,4-oxadiazole 
• 104-85-8 para-methylbenzonitrile 
• 111480-69-4 5-(4-nitrophenylthio)-3-(4-tolyl)-1,2,4-thiadiazole 
• 111480-70-7 3-(4-methoxyphenyl)-5-(4-nitrophenylthio)-1,2,4-thiadiazole 
• 92323-58-5 1-nitro-4-(octylsulfanyl)benzene 

Relevant articles and documents

Practical access to aromatic thiocyanates by CuCN-mediated direct aerobic oxidative cyanation of thiophenols and diaryl disulfides

The practical and mild aerobic oxidative CuCN-mediated cyanation of thiophenols and diaryl disulfides was investigated. The reaction was performed in air at room temperature and reached aromatic thiocyanates in moderate to good yields starting from a broad range of diversely functionalized substrates.

Synthesis of Thio-/Selenopyrrolines via SnCl4-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thio-/Selenocyanates

A straightforward protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition of aryl thio-/selenocyanates with donor-acceptor cyclopropanes (DACs) in the presence of SnCl4 as a Lewis acid catalyst. Further, good chemoselectivity was observed when DACs were treated with 3-cyano phenyl thiocyanate. These results suggest that thiocyanate is more reactive than nitrile moiety in such (3+2)-cycloaddition reactions.

Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions

The electrochemical generation of aryldiazonium salts from nitroarenes in a two-phase system (ethyl acetate/water) was reported for the first time. Some compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.

Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates

Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.