74394-96-0

Basic information

• Product Name: (2E)-3-phenylprop-2-en-1-yl thiocyanate
• Synonyms: (2E)-3-Phenylprop-2-en-1-yl thiocyanate; thiocyanic acid, (2E)-3-phenyl-2-propen-1-yl ester; thiocyanic acid, (2E)-3-phenyl-2-propenyl ester
• CAS NO: 74394-96-0
• Molecular Formula: C₁₀H₉NS
• Molecular Weight: 175.2502
• Mol File: 74394-96-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 327.2°C at 760 mmHg
• Flash Point: 151.7°C
• Density: 1.136g/cm³
• Vapor Pressure: 0.000205mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: (2E)-3-phenylprop-2-en-1-yl thiocyanate(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-phenylprop-2-en-1-yl thiocyanate(74394-96-0)
• EPA Substance Registry System: (2E)-3-phenylprop-2-en-1-yl thiocyanate(74394-96-0)

Safety Data

• Hazardous Substances Data: 74394-96-0(Hazardous Substances Data)

Usage

General Description

(2E)-3-phenylprop-2-en-1-yl thiocyanate is a chemical compound with the molecular formula C11H9NOS. It is a colorless to yellow liquid with a strong odor and is commonly used in the manufacturing of perfumes and other fragrances. (2E)-3-phenylprop-2-en-1-yl thiocyanate is known for its thiocyanate group, which has potential applications in organic synthesis and chemical reactions. Additionally, it may also have potential health effects as it is a known irritant to the skin, eyes, and respiratory system. Overall, (2E)-3-phenylprop-2-en-1-yl thiocyanate is a versatile compound that has both industrial and potentially hazardous properties.

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 
• 109283-53-6 trimethylsilyl cinnamyl ether 
• 71700-50-0 1-(tert-butyldimethylsilyloxy)-3-phenyl-2-propene 
• 104-54-1 3-Phenylpropenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 103205-11-4 Vinyl-phenyl-acetamid 
• 30953-25-4 2-phenylbut-3-enoic acid 
• 505-14-6 thiocyanogen 
• 75-15-0 carbon disulfide 

Downstream Products

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

Relevant articles and documents

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.

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.

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.