6097-27-4

Basic information

• Product Name: 4-METHYLPHENACYL THIOCYANATE
• Synonyms: 2-(4-METHYLPHENYL)-2-OXOETHYL THIOCYANATE;4-METHYLPHENACYL THIOCYANATE;4-METHYLPHENACYL THIOCYANATE, 95+%;2-(cyanosulfanyl)-1-(4-Methylphenyl)ethan-1-one;4-(Thiocyanatoacetyl)toluene, 4-Methylphenacyl thiocyanate
• CAS NO: 6097-27-4
• Molecular Formula: C₁₀H₉NOS
• Molecular Weight: 191.25
• EINECS: 604-604-1
• Mol File: 6097-27-4.mol

Chemical Properties

• Melting Point: 105-107
• Boiling Point: 352.2 °C at 760 mmHg
• Flash Point: 166.8 °C
• Appearance: /
• Density: 1.187 g/cm³
• Vapor Pressure: 3.9E-05mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 4-METHYLPHENACYL THIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLPHENACYL THIOCYANATE(6097-27-4)
• EPA Substance Registry System: 4-METHYLPHENACYL THIOCYANATE(6097-27-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6097-27-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-METHYLPHENACYL THIOCYANATE is used as a reactive intermediate for the synthesis of various organic compounds. Its unique structure and reactivity make it a key component in creating new molecules with specific properties.
Used in Chemical Research:
In the field of chemical research, 4-METHYLPHENACYL THIOCYANATE is utilized as a model compound to study the properties and reactions of thiocyanate derivatives. This helps in understanding the behavior of similar compounds and contributes to the advancement of chemical knowledge.
Used in Pharmaceutical Production:
4-METHYLPHENACYL THIOCYANATE is used as a building block in the production of pharmaceuticals. Its ability to participate in various chemical reactions allows for the creation of drug molecules with desired therapeutic properties.
Used in Agrochemical Production:
4-METHYLPHENACYL THIOCYANATE also finds application in the agrochemical industry, where it is used in the synthesis of pesticides and other agrochemicals. Its reactivity and functional group contribute to the development of effective products for agricultural use.
Used as an Intermediate in Various Industries:
4-METHYLPHENACYL THIOCYANATE serves as an intermediate in the synthesis of other compounds used across different industries. Its versatility in participating in chemical reactions makes it a valuable precursor for the production of a wide range of products.

InChI:InChI=1/C10H9NOS/c1-8-2-4-9(5-3-8)10(12)6-13-7-11/h2-5H,6H2,1H3

Upstream product

• 619-41-0 4-(bromoacetyl)toluene 
• 27130-71-8 4,5-dihydro-3-methyl-5-oxopyrazole-1-carbothioamide 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 7677-24-9 trimethylsilyl cyanide 
• 122-00-9 para-methylacetophenone 
• 66616-85-1 α-(4-methylphenyl)acrylic acid 
• 1147550-11-5 ammonium thiocyanate 
• 1392296-72-8 N-benzyl-N-(1-(p-tolyl)vinyl)acetamide 
• 766-97-2 4-n-methylphenylacetylene 
• 540-72-7 sodium thiocyanide 
• 333-20-0 potassium thioacyanate 
• 344790-87-0 1-butyl-3-methylimidazolium thiocyanate 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 10514-46-2 3-methyl-pyrazole-1-carbothioic acid amide 

Downstream Products

• 128896-84-4 4-(4-Methyl-phenyl)-2-(4-methyl-piperazino)-thiazol 
• 82000-28-0 2-p-Methylbenzoyl-5H-thiadiazolo<2,3-b>quinazoline-5-one 
• 119665-45-1 4-(4-methylphenyl)-N,N-dimethylthiazol-2-amine 
• 344238-41-1 2-[2-(2-Oxo-2-p-tolyl-ethyl)-isothioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 106511-52-8 1-p-Tolyl-7,9-dioxa-3-thia-4,10b-diaza-dicyclopenta[a,g]naphthalen-5-one 
• 137538-91-1 1-phenyl-6-phenylazo-3,6-di-p-tolyl-1,4,5,6-tetrahydro-pyridazine 
• 128699-85-4 N,N'-Dimethyl-N,N'-bis<4-(4-methyl-phenyl)-thiazol-2-yl>-1,2-diaminoethane 
• 137538-90-0 N-[4-p-Tolyl-5H-thiazol-(2E)-ylidene]-N'-[4-p-tolyl-5H-thiazol-(2Z)-ylidene]-hydrazine 
• 79576-72-0 C₂₀H₁₆N₂S₃ 
• 2103-90-4 4-(4-methylphenyl)-2-oxo-thiazole 
• 3884-32-0 2-chloro-4-(4-methylphenyl)-1,3-thiazole 
• 13145-56-7 1,4-bis(4-tolyl)butane-1,4-dione 
• 65263-09-4 3,6-bis(4-methylphenyl)-2,7-dihydro-1,4,5-thiadiazepine 
• 1257425-11-8 3-(pyridine-4-ylmethyl)-4-p-tolylthiazol-2(3H)imine 

Relevant articles and documents

K2S2O8-mediated regio- And stereo-selective thiocyanation of enamides with NH4SCN

A direct and straightforward thiocyanation of enamides with NH4SCN under metal-free conditions has been accomplished. A variety of (E)-β-thiocyanoenamides are readily produced in a regio- and stereo-selective manner. The protocol features mild reaction conditions, good functional group tolerance and operational simplicity. The potential utility of this strategy was further demonstrated by transformation of thiocyanate into thiotetrazole-containing compounds and a Pd-catalyzed cross-coupling reaction to afford six- or seven-membered sulfur-containing heterocycles. Mechanistic insights into the reaction indicate that the reaction may proceedviaa radical mechanism.

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.

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.

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.

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.

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.

Molecular oxygen induced free radical oxythiocyanation of styrenes leading to α-oxothiocyanates

A facile and efficient protocol of oxythiocyanation of styrenes with ammonium thiocyanate has been developed. The reaction proceeded at room temperature using oxygen as sole oxidant to afford the α-oxothiocyanates via radical pathway in moderate to good yields. This method is straightforward, green and cost-effective, requires no catalyst and additives.