1-(Ethenylthio)-2-methylbenzene

Base Information

• Chemical Name: 1-(Ethenylthio)-2-methylbenzene
• CAS No.: 7297-72-5
• Molecular Formula: C₉H₁₀S
• Molecular Weight: 150.244
• DSSTox Substance ID: DTXSID401303281
• Mol file: 7297-72-5.mol

Synonyms:1-(Ethenylthio)-2-methylbenzene;SCHEMBL4209146;DTXSID401303281;7297-72-5

Chemical Property of 1-(Ethenylthio)-2-methylbenzene

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 150.05032149
• Heavy Atom Count: 10
• Complexity: 109

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=CC=C1SC=C

Technology Process of 1-(Ethenylthio)-2-methylbenzene

There total 9 articles about 1-(Ethenylthio)-2-methylbenzene 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: 93.0%

2,2-diphenyl-1,3-oxathiolane (33735-40-9) + 2-methylphenyl bromide (95-46-5) → 2-methylphenyl vinyl sulfide (7297-72-5)

Guidance literature:

With palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); potassium tert-butylate; at 70 ℃; for 22h;

DOI:10.1021/acs.orglett.6b03249

Reference yield: 90.0%

calcium carbide (75-20-7) + 2-thiocresol (137-06-4) → 2-methylphenyl vinyl sulfide (7297-72-5)

Guidance literature:

With water; potassium hydroxide; In N,N-dimethyl-formamide; at 100 ℃; for 3h; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/c5gc01552a

Reference yield: 52.0%

2,2-dimethyl-1,3-oxathiolane (5684-31-1) + 2-methylphenyl bromide (95-46-5) → 2-methylphenyl vinyl sulfide (7297-72-5)

Guidance literature:

With 18-crown-6 ether; Xantphos-Pd-G₃; potassium tert-butylate; at 70 ℃; for 12h;

DOI:10.1021/acs.orglett.6b03249

upstream raw materials:

2-thiocresol

acetylene

bis(2-methylphenyl)disulfide

vinyl magnesium bromide

Downstream raw materials:

ethynyl-o-tolyl sulfide

o-tolyl vinyl sulfoxide

(ξ-2-bromo-vinyl)-o-tolyl sulfide

1-(vinylsulfonyl)-2-methylbenzene

Refernces

• 1、 Rodygin, Konstantin S.,Ananikov, Valentine P.. "An efficient metal-free pathway to vinyl thioesters with calcium carbide as the acetylene source". supporting information. p. 482 - 486. Retrieved 2016/01/30.
• 2、 Rodriguez Rivero, Marta,Alonso, Ines,Carretero, Juan C.. "Vinyl sulfoxides as stereochemical controllers in intermolecular Pauson-Khand reactions: Applications to the enantioselective synthesis of natural cyclopentanoids". . p. 5443 - 5459. Retrieved 2007/10/03.