19339-59-4

Usage

Chemical Properties

white to off-white needles or crystals

InChI:InChI=1/C9H6ClNOS/c10-8-3-1-7(2-4-8)9(12)5-13-6-11/h1-4H,5H2

Upstream product

• 1124-15-8 3,5-dimethyl-1H-pyrazole-1-carbothioamide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 937-20-2 p-chlorophenacyl chloride 
• 25917-49-1 1-(4-chlorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 333-20-0 potassium thioacyanate 
• 99-91-2 para-chloroacetophenone 
• 128228-95-5 3-trifluoromethyl-5-(2-thienyl)-pyrazol-1-thiocarboxamide 
• 1073-67-2 4-vinylbenzyl chloride 
• 1147550-11-5 ammonium thiocyanate 
• 540-72-7 sodium thiocyanide 
• 873-73-4 4-n-chlorophenylacetylene 
• 7677-24-9 trimethylsilyl cyanide 
• 51747-43-4 2-(4-chlorophenyl)-acrylic acid 
• 344790-87-0 1-butyl-3-methylimidazolium thiocyanate 

Downstream Products

• 2104-00-9 4-(4'-chloro)-phenyl-Δ-4-thiazolene-2-thione 
• 2103-98-2 4-(4-chlorophenyl)-2,3-dihydro-2-oxo-thiazole 
• 2103-96-0 2-chloro-4-(4-chlorophenyl)thiazole 
• 23998-06-3 4-(4-chloro-phenyl)-2,2'-diimino-3'-phenyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-08-5 4-(4-chloro-phenyl)-2,2'-diimino-3'-p-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 23998-07-4 4-(4-chloro-phenyl)-2,2'-diimino-3'-o-tolyl-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 66373-65-7 1-(4-chloro-phenyl)-benzo[g]thiazolo[3,2-a]quinazolin-5-one 
• 65679-05-2 4-(4-chloro-phenyl)-3-naphthalen-2-yl-3H-thiazol-2-ylideneamine 
• 23998-09-6 4-(4-chloro-phenyl)-3'-(2-chloro-phenyl)-2,2'-diimino-2',3'-dihydro-[3,4']bithiazolyl-5'-carboxylic acid ethyl ester 
• 39564-86-8 2-bromo-4-(4-chlorophenyl)thiazole 
• 128016-19-3 4-(4-Chlor-phenyl)-2-piperidino-thiazol 
• 82000-29-1 2-p-Chlorobenzoyl-5H-thiadiazolo<2,3-b>quinazoline-5-one 
• 344238-42-2 2-{2-[2-(4-Chloro-phenyl)-2-oxo-ethyl]-isothioureido}-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 106527-70-2 1-(4-Chloro-phenyl)-7,9-dioxa-3-thia-4,10b-diaza-dicyclopenta[a,g]naphthalen-5-one 

Relevant academic research and scientific papers

A task-specific ionic liquid [bmim]SCN for the conversion of alkyl halides to alkyl thiocyanates at room temperature

A new task-specific ionic liquid (TSIL), 1-n-butyl-3- methylimidazolium thiocyanate ([bmim]SCN), has been prepared and used for the first time as the medium as well as reactant for the synthesis of alkyl thiocyanates from the corresponding alkyl halides by thiocyanate-halide exchange at room temperature. The alkyl thiocyanate products can be easily isolated from the reaction mixture by simple extraction and the ionic liquid 1-n-butyl-3-methylimidazolium halide may be reused for the synthesis of the ionic liquid [bmim]SCN and recycled for further use.

Photo-sensitized oxy-thiocyanation of terminal alkynes/1,3-aryldienes and their one-pot conversion to 2-hydroxy 4-substituted aryl thiazoles

A regioselective visible light induced synthesis of aryl α-thiocyano ketones/thiocyano alcohols from activated terminal aryl alkynes and aryl 1,3-conjugated dienes was achieved. This mild and non-metallic oxidation is exclusively driven by benign ambient air in the presence of an organic photo-catalyst and NH4SCN. This protocol was also demonstrated at the 5 mmol scale for the synthesis of potentially therapeutic 2-hydroxy 4-substituted arylthiazoles in good yields, signifying its amenability for large-scale application.

α-Selective C(sp3)-H Thio/Selenocyanation of Ketones with Elemental Chalcogen

A facile method is disclosed for the synthesis of α-thio/selenocyanato ketones through regioselective C-H thio/selenocyanation of ketones. The advantages include the use of easily available starting materials, high efficiency, simple operation, and easy scale-up. Control experiments provide evidence that the reaction proceeded via a radical way, while kinetic isotope effect experiments reveal that the cleavage of the C-H bond serves as the rate-limiting step.

Visible-Light-Mediated Additive-Free Decarboxylative Ketonization Reaction of Acrylic Acids: An Access to α-Thiocyanate Ketones

Visible-light-mediated additive-free decarboxylative functionalization of acrylic acids has been developed. The reaction uses inexpensive organic dye 9,10-dicyanoanthracene as a photocatalyst and uses the ubiquitous dioxygen as both an oxygen source and an oxidant. Through this mild and environmentally friendly method, a series of important α-thiocyanate ketones can be generated from easily available acrylic acids and ammonium thiocyanate. In addition, the facile transformation of product α-thiocyanate ketones makes this method have great potential for application in organic and pharmaceutical chemistry.

Boron-doped TiO2(B-TiO2): visible-light photocatalytic difunctionalization of alkenes and alkynes

Boron-doped TiO2(B-TiO2) was prepared, characterized, and successfully applied as a reusable, inexpensive, available, and heterogeneous nanophotocatalyst under visible light for a novel method of construction of phenacyl thiocyanate compounds from double or triple bonds. Impressive aspects of this project are obtaining the desired compounds in a short time, using a renewable energy source, and using a catalyst with easy extraction that is solvent-safe, and without the use of any oxidants, bases, and ligands, or harsh conditions. This is the first report of the construction of phenacyl thiocyanates through this photocatalytic method under visible light.

Visible-light-promoted thiocyanation of sp2C-H bonds over heterogeneous graphitic carbon nitrides

Mesoporous graphitic carbon nitride (mpg-C3N4) has been developed as a metal-free heterogeneous photocatalyst for thiocyanation transformations. The reaction proceeds efficiently by utilizing air as a green oxidant under mild reaction conditions, which affords SCN-containing compounds in moderate to excellent yields. Meanwhile, the practicality of this protocol is further demonstrated by the reusability of the mpg-C3N4photocatalyst and the scaled-up reaction. Furthermore, detailed mechanistic studies clearly demonstrate the role of oxygen.

Visible-Light-Promoted Difunctionalization of Olefins Leading to α-Thiocyanato Ketones

A simple and convenient visible-light-induced difunctionalization of alkenes with ammonium thiocyanate and dioxygen has been developed at room temperature. A series of α-thiocyanato ketones could be easily and efficiently obtained in moderate to good yields through the formation of C-S and C=O bonds simply by using nontoxic and inexpensive Na 2 -Eosin Y as a photocatalyst.

Ammonium [11C]thiocyanate: revised preparation and reactivity studies of a versatile nucleophile for carbon-11 radiolabelling

Herein we report the preparation of ammonium [11C]thiocyanate via the reaction of [11C]CS2 with ammonia. The [11C]SCN- ion is demonstrated as a potent nucleophile that can be used to readily generate a range of 11C-labelled thiocyanate molecules in high conversions. Furthermore, novel 11C-labelled thiazolone molecules can be easily prepared from the intermediate α-thiocyanatophenones via an acid mediated cyclisation reaction.

One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)

An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.

A 2-thiocyano HYPNONE derivatives method for the preparation of

The invention discloses a method for preparing 2-sulfur cyano acetophenone derivatives. The method for preparing the 2-sulfur cyano acetophenone derivatives comprises the following steps: dissolving styrene derivatives and ammonium thiocyanate in a solvent, and reacting at 20-30 DEG C to obtain 2-sulfur cyano acetophenone derivatives. According to the method for preparing the 2-sulfur cyano acetophenone derivatives, the styrene derivatives are taken as starting materials; the raw materials are easily available and various in type; products prepared by the method have various in type, can be directly used and can also be used for other further reactions; meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-processing process; an accelerant does not need to be added; the production process meets the green and chemical requirements, is relatively high in yield and is suitable for large-scale production.