3-Methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile

Base Information

• Chemical Name: 3-Methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile
• CAS No.: 93604-51-4
• Molecular Formula: C14H15NS
• Molecular Weight: 229.346
• DSSTox Substance ID: DTXSID50538803
• Mol file: 93604-51-4.mol

Synonyms:93604-51-4;3-methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile;DTXSID50538803;3-methyl-4-(phenylsulfanyl)-3-cyclohexene-1-carbonitrile;3-Methyl-4-(phenylsulfanyl)cyclohex-3-ene-1-carbonitrile

Chemical Property of 3-Methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile

Chemical Property:

• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 229.09252066
• Heavy Atom Count: 16
• Complexity: 317

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CCC(C1)C#N)SC2=CC=CC=C2

Technology Process of 3-Methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile

There total 3 articles about 3-Methyl-4-phenylsulfanylcyclohex-3-ene-1-carbonitrile 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: 77.0%

2-methyl-3-(phenylthio)-1,3-butadiene (91891-84-8) + acrylonitrile (107-13-1,25014-41-9) → 3-Methyl-4-phenylsulfanyl-cyclohex-3-enecarbonitrile (93604-51-4)

Guidance literature:

With zinc(II) chloride; In diethyl ether; at 25 ℃; for 48h;

DOI:10.1021/jo00201a034

Reference yield:

3-methyl-4-(phenylthio)-2,5-dihydrothiophene 1,1-dioxide (93604-54-7) → 3-Methyl-4-phenylsulfanyl-cyclohex-3-enecarbonitrile (93604-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 170 °C

2: 77 percent / ZnCl₂ / diethyl ether / 48 h / 25 °C

With zinc(II) chloride; In diethyl ether;

DOI:10.1021/jo00201a034

Reference yield:

benzenesulfenyl chloride (931-59-9) → 3-Methyl-4-phenylsulfanyl-cyclohex-3-enecarbonitrile (93604-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) NEt₃ / 1.) CH₂Cl₂, a.) 25 deg C, 4 d, b.) reflux, 1 d, 2.) 25 deg C, 2 d

2: 80 percent / 170 °C

3: 77 percent / ZnCl₂ / diethyl ether / 48 h / 25 °C

With triethylamine; zinc(II) chloride; In diethyl ether;

DOI:10.1021/jo00201a034

upstream raw materials:

2-methyl-3-(phenylthio)-1,3-butadiene

acrylonitrile

3-methyl-4-(phenylthio)-2,5-dihydrothiophene 1,1-dioxide

benzenesulfenyl chloride

Downstream raw materials:

1-methyl-4-cyanocyclohex-1-ene