trans-2-phenylethenyl isothiocyanate

Base Information

• Chemical Name: trans-2-phenylethenyl isothiocyanate
• CAS No.: 54898-80-5
• Molecular Formula: C₉H₇NS
• Molecular Weight: 161.227
• Mol file: 54898-80-5.mol

Synonyms:trans-2-phenylethenyl isothiocyanate

Chemical Property of trans-2-phenylethenyl isothiocyanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-2-phenylethenyl isothiocyanate

There total 3 articles about trans-2-phenylethenyl isothiocyanate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(2E)-N-hydroxy-3-phenylacrylimidoyl chloride (105363-16-4) → trans-2-phenylethenyl isothiocyanate (54898-80-5)

Guidance literature:

With OuadraPure Thiaurea resin; SIO₂-pyridine; In acetonitrile; at 50 ℃; for 0.166667h; Flow reactor;

DOI:10.3762/bjoc.9.184

Reference yield: 6.0%

benzaldehyde (100-52-7) + tris(trimethylsilyl)methyl isothiocyanate (83272-74-6) → trans-2-phenylethenyl isothiocyanate (54898-80-5) + 4-benzyl-5-phenyl-4-oxazoline-2-thione (83272-79-1) + α-(trimethylsilyl)styryl isothiocyanate

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1246/bcsj.55.1163

Reference yield:

benzaldehyde (100-52-7) + bis(triemthylsilyl)methyl isothiocyanate (76124-50-0) → cis-2-phenylethenyl isothiocyanate (54898-79-2) + trans-2-phenylethenyl isothiocyanate (54898-80-5) + 5-Phenyl-4-(trimethylsilyl)oxazolidin-2-thion (76124-54-4)

Guidance literature:

With tetrabutyl ammonium fluoride; water; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, RT, 8 h;

DOI:10.1246/bcsj.55.1163

upstream raw materials:

benzaldehyde

bis(triemthylsilyl)methyl isothiocyanate

tris(trimethylsilyl)methyl isothiocyanate

(2E)-N-hydroxy-3-phenylacrylimidoyl chloride

Downstream raw materials:

4-oxo-5-phenyl-3-triphenylphosphorano-2-pyridinethione

Refernces

• 1、 Hirao,Yamada,Hayashi,et al.. "New building blocks for heterocyclic syntheses. Silylated methyl isothiocyanates". . p. 1163 - 1167. Retrieved 2007/10/02.