55757-32-9

Basic information

• Product Name: 2-BROMOPHENYLTHIOCYANATE
• Synonyms: 2-BROMOPHENYLTHIOCYANATE
• CAS NO: 55757-32-9
• Molecular Formula: C₇H₄BrNS
• Molecular Weight: 214.08236
• Mol File: 55757-32-9.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMOPHENYLTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOPHENYLTHIOCYANATE(55757-32-9)
• EPA Substance Registry System: 2-BROMOPHENYLTHIOCYANATE(55757-32-9)

Safety Data

• Hazardous Substances Data: 55757-32-9(Hazardous Substances Data)

Upstream product

• 540-72-7 sodium thiocyanide 
• 10448-07-4 2-bromobenzenediazonium tetrafluoroborate 
• 6320-02-1 o-bromothiophenol 
• 333-20-0 potassium thioacyanate 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 615-36-1 2-bromoaniline 

Downstream Products

• 15861-48-0 2-bromophenyl phenyl sulfide 

Relevant articles and documents

5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations

The synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.

Transition-metal-free synthesis of thiocyanato- or nitro-arenes through diaryliodonium salts

A transition-metal-free approach to facile synthesis of thiocyanato- and nitro-arenes was developed from KSCN (potassiumthiocyanate) or NaNO2with diaryliodonium salts in good yields under mild conditions. The reaction was compatible with a variety of sensitive functional substituents such as halides and nitro and ester groups. The usefulness of arylation products has been realized. (Formula Present).

A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS

A facile and efficient transformation of arylboronic acids to their corresponding aryl thiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under oxygen atmosphere, the transformation can be readily conducted at ambient temperature. The newly-developed protocol provided a competitive synthetic approach to aryl thiocyanates that can tolerate a broad range of reactive functional groups and/or strong electron-withdrawing groups.