74394-96-0

Usage

Uses

Used in Perfumery and Fragrance Industry:
(2E)-3-phenylprop-2-en-1-yl thiocyanate is utilized as a key ingredient in the manufacturing of perfumes and other fragrances. Its distinctive scent and stability make it a valuable component in creating a wide range of olfactory products.
Used in Organic Synthesis:
The thiocyanate group present in (2E)-3-phenylprop-2-en-1-yl thiocyanate offers potential applications in organic synthesis. It can be used as a reagent or intermediate in the production of various organic compounds, contributing to the development of new chemical entities.
Used in Chemical Reactions:
Due to its reactive thiocyanate group, (2E)-3-phenylprop-2-en-1-yl thiocyanate can participate in a variety of chemical reactions. This makes it a versatile compound for research and industrial processes, where it can be employed to modify or create new molecules.
Caution: Health and Safety

Upstream product

• 333-20-0 potassium thioacyanate 
• 4392-24-9 Cinnamyl bromide 
• 64-17-5 ethanol 
• 540-72-7 sodium thiocyanide 
• 1147550-11-5 ammonium thiocyanate 
• 2687-12-9 cinnamyl chloride 
• 75-15-0 carbon disulfide 
• 4393-21-9 1-(phenyl)allylamine 
• 104-54-1 3-Phenylpropenol 
• 109283-53-6 trimethylsilyl cinnamyl ether 
• 71700-50-0 1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 103205-11-4 Vinyl-phenyl-acetamid 
• 30953-25-4 2-phenylbut-3-enoic acid 

Downstream Products

• 55765-63-4 C₁₈H₁₈S₂ 
• 79528-83-9 (3-thiocyanatopropyl)benzene 
• 20332-96-1 1,2-dicinnamyldisulfane 
• 65788-85-4 3-phenylallyl isothiocyanate 
• 1092497-92-1 C₁₂H₁₄S 
• 65984-69-2 N-phenyl-N'-trans-cinnamyl-thiourea 
• 474055-66-8 ((E)-3-isothiocyanatoprop-1-enyl)benzene 

Relevant academic research and scientific papers

Substituted alkenyl thiocyanate compound and preparation method thereof

The invention discloses a substituted alkenyl thiocyanate compound and a preparation method thereof. The preparation method comprises the following steps: stirring substituted allyl alcohol serving as a raw material, potassium persulfate serving as an oxidizing agent and ammonium thiocyanate serving as a thiocyanate source at room temperature to react in a mixed solvent, monitoring the reaction through a TLC (Thin Layer Chromatography) plate until the reaction is complete, extracting by using ethyl acetate, carrying out reduced pressure distillation on the mixed solution, and evaporating to remove the solvent, performing column chromatography on the crude product to obtain alkenyl thiocyanate; in the reaction, a metal catalyst does not need to be additionally added, ammonium thiocyanate is oxidized into thiocyanate free radicals under the oxidation condition of potassium persulfate, then the free radicals carry out electrophilic attack on substituted allyl alcohol, an active alkyl free radical intermediate is obtained to induce uniform cracking of carbon-oxygen bonds, and finally the alkenyl thiocyanate compound with thermodynamic stability is generated. The method has the advantages of simplicity in operation, mild reaction conditions, wide substrate universality, easiness in large-scale production, low cost and the like.

AIBN-initiated direct thiocyanation of benzylic sp3C-H with: N -thiocyanatosaccharin

Direct thiocyanations of benzylic compounds have been implemented. Here, a new strategy, involving a free radical reaction pathway initiated by AIBN, was used to construct the benzylic sp3 C-SCN bond. In this way, the disadvantage of other strategies involving introducing leaving groups in advance to synthesize benzyl thiocyanate compounds was overcome. The currently developed protocol also involved the use of readily available raw materials and resulted in high product yields (up to 100%), both being great advantages for synthesizing benzyl thiocyanates.

Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates

A novel SO 2F 2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C-O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.

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.

Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide

A convenient procedure for one-pot conversion of alcohols into the corresponding alkyl thiocyanates in the presence of cross-linked poly (N-propyl-4-vinylpyridinium) thiocyanate ion [P4-VP]Pr-SCN, promoted by cyanuric chloride/dimethylformamide, is described. Various alcohols were converted to their corresponding alkyl thiocyanates and it was observed that substituted benzyl alcohol with electron-withdrawing or electron-donating groups were transformed into the corresponding benzyl thiocyanate derivatives in high to excellent yields in a short reaction time but, sterically hindered alcohols produced the corresponding thiocyanates in very low yields.

A convenient, rapid, and general synthesis of α-oxo thiocyanates using clay supported ammonium thiocyanate

A very rapid, convenient, and general method for the synthesis of α-oxo thiocyanates has been described by using clay supported ammonium thiocyanate. The procedure avoids the use of additional catalyst, solvent, aqueous work-up and the yields are high. Moreover, the method is applicable for a variety of aryl, heteroaryl, alkyl α-halo carbonyls, β-keto tosylates, α-halo β-dicarbonyl, α-tosyl, β-dicarbonyl, alkyl halide, and alkyl tosylates.

Novel synthesis of allyl and cyclopropylcarbinyl thiocyanates by the reaction of organocobaloximes with thiocyanogen

Thiocyanogen reacts in aprotic solvents with allyl and but-3-enyl cobaloximes to give moderate yields of allyl and cyclopro-pylcarbinyl thiocyanates. Using this method highly unstable allyl thiocyanates may be prepared in situ at low temperature. Their rearrangement to isothiocyanates is observed at sub-zero temperatures.

Optimized access to alkyl thiocyanates

Functionalized alkyl thiocyanates are synthesized in high yields from corresponding halides via in situ formation of tetra n-butylammonium thiocyanate. Use of this mild but efficient thiocyanation reagent limits the amounts of by-products.

Efficient conversion of silyl ethers to thiocyanates with Ph3P(SCN)2

A new and efficient method for the conversion of primary and secondary alkyl, aryl, allyl and benzyl silyl ethers to their corresponding thiocyanates by in-situ generation of Ph3P(SCN)2 is described. The reactions occur immediately at room temperature and provide high to excellent yields of thiocyantes.

Efficient one-pot thiocyanation of primary, secondary and tertiary alcohols by in situ generation of Ph3P(SCN)2. A modified procedure

The preparation of Ph3P(SCN)2 is modified by using a combination of Ph3P, NH4SCN and Br2 at room temperature for the efficient conversion of primary, secondary and tertiary alcohols to their corresponding thiocyanates in excellent yields.