(E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: (E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate
• CAS No.: 237435-26-6
• Molecular Formula: C₁₆H₁₃NO₃S
• Molecular Weight: 299.35
• DSSTox Substance ID: DTXSID80442883
• Wikidata: Q82260457
• Mol file: 237435-26-6.mol

Synonyms:237435-26-6;(E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate;(E)-2-cyano-1-phenylethenyl 4-methylbenzenesulfonate;[(E)-2-cyano-1-phenylethenyl] 4-methylbenzenesulfonate;GD-0756;(2E)-3-[(4-methylbenzenesulfonyl)oxy]-3-phenylprop-2-enenitrile;SCHEMBL5774107;(E)-2-CYANO-1-PHENYLETHENYL4-METHYLBENZENESULFONATE;DTXSID80442883;MFCD12827816;STL083754;AKOS001774059;(E)-2-Cyano-1-phenylvinyl4-methylbenzenesulfonate;J-501851;F6548-0589

Chemical Property of (E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate

Chemical Property:

• Melting Point: 87-89°
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 299.06161445
• Heavy Atom Count: 21
• Complexity: 510

Purity/Quality:

98%min ^*data from raw suppliers

(E)-2-Cyano-1-phenylethenyl4-methylbenzenesulfonate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC(=CC#N)C2=CC=CC=C2
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O/C(=C/C#N)/C2=CC=CC=C2

Technology Process of (E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate

There total 3 articles about (E)-2-Cyano-1-phenylvinyl 4-methylbenzenesulfonate 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: 90.0%

3-oxo-3-phenylpropanamide (3446-58-0) + p-toluenesulfonyl chloride (98-59-9) → 2-cyano-1-phenylvinyl-4-methylbenzenesulfonate (237435-26-6)

Guidance literature:

With pyridine; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1016/j.tet.2016.06.068

Reference yield: 62.0%

pyridine (110-86-1) + 3-oxo-3-phenylpropanamide (3446-58-0) + p-toluenesulfonyl chloride (98-59-9) → C28H24N2O5S2 + 2-cyano-1-phenylvinyl-4-methylbenzenesulfonate (237435-26-6)

Guidance literature:

In dichloromethane; at 0 ℃; for 24h; regioselective reaction;

DOI:10.1016/j.tet.2016.06.068

Reference yield: 57.0%

Benzoylacetonitrile (614-16-4) + p-toluenesulfonyl chloride (98-59-9) → 2-cyano-1-phenylvinyl-4-methylbenzenesulfonate (237435-26-6)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 22 ℃; for 23h;

DOI:10.1021/jm000269t

upstream raw materials:

Benzoylacetonitrile

p-toluenesulfonyl chloride

pyridine

3-oxo-3-phenylpropanamide

Downstream raw materials:

ethyl 3-amino-5-phenyl-1H-pyrrole-2-carboxylate

tert-butyl 2-aza-3-[(tert-butoxy)carbonylamino]-3-{[2-(ethoxycarbonyl)-5-phenylpyrrol-3-yl]amino}prop-2-enoate