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 
• 74-90-8 hydrogen cyanide 
• 100-32-3 di(p-nitrophenyl) disulfide 
• 2942-58-7 diethyl cyanophosphonate 
• 15959-31-6 sodium 4-nitrobenzenesulfinate 
• 701-57-5 1-methylthio-4-nitro-benzene 
• 1147550-11-5 ammonium thiocyanate 
• 1849-36-1 para-nitrobenzenethiol 
• 100-25-4 para-dinitrobenzene 
• 540-72-7 sodium thiocyanide 
• 3425-46-5 potassium selenocyanate 

Downstream Products

• 100-32-3 di(p-nitrophenyl) disulfide 
• 60951-95-3 C₉H₁₀N₂O₃S 
• 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 
• 7205-60-9 1-(ethylsulfanyl)-4-nitrobenzene 
• 71533-01-2 1-(2-Methoxy-ethylsulfanyl)-4-nitro-benzene 
• 71532-97-3 1-methylsulfanyl-2-(4-nitro-phenylsulfanyl)-ethane 
• 71532-93-9 1,2-bis(4-nitrophenylthio) ethane 
• 71532-95-1 C₁₄H₁₂N₂O₄S₂ 
• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 62291-64-9 1-cyclohexylsulfanyl-4-nitrobenzene 
• 7677-24-9 trimethylsilyl cyanide 

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.

Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides

An efficient chemoselective protocol has been developed for the synthesis of thiosulfonates and thiocyanates by employing cost effective and commercially available organosulfonyl chlorides with potassium thio-/selenocyanate. The strategy offered the thiosulfonates and thiocyanates selectively by tuning the equivalents of KSeCN and optimizing the reaction temperature. On the other hand, thiosulfonates were obtained as sole products when organosulfonyl chlorides were treated with KSCN. Furthermore, the syntheses of diarylthioethers and aryl(heteroaryl) thioethers were carried out as a part of synthetic application of newly prepared arylthiocyanates.

Selectfluor-initiated cyanation of disulfides to thiocyanates

A Selectfluor-initiated cyanation of disulfides to thiocyanates has been developed. In this process, Selectfluor was employed as the oxidant and trimethylsilyl cyanide was used as the cyanation reagent. It provides an eco-friendly and simple way to synthesize the thiocyanates.

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.