4-Chlorophenyl methyl sulfoxide, (R)-

Base Information

• Chemical Name: 4-Chlorophenyl methyl sulfoxide, (R)-
• CAS No.: 28227-63-6
• Molecular Formula: C7H7ClOS
• Molecular Weight: 174.651
• UNII: 1I52KC5461
• Wikidata: Q27896907
• Mol file: 28227-63-6.mol

Synonyms:(R)-p-Chlorophenyl methyl sulfoxide;1I52KC5461;4-Chlorophenyl methyl sulfoxide, (+)-;4-Chlorophenyl methyl sulfoxide, (R)-;1-Chloro-4-((R)-methylsulfinyl)benzene;Benzene, 1-chloro-4-((R)-methylsulfinyl)-;UNII-1I52KC5461;(r)-4-chlorophenyl methyl sulfoxide;28227-63-6;SCHEMBL15109075;Q27896907

Chemical Property of 4-Chlorophenyl methyl sulfoxide, (R)-

Chemical Property:

• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.9906137
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)C1=CC=C(C=C1)Cl
• Isomeric SMILES: C[S@@](=O)C1=CC=C(C=C1)Cl

Technology Process of 4-Chlorophenyl methyl sulfoxide, (R)-

There total 31 articles about 4-Chlorophenyl methyl sulfoxide, (R)- 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: 99.0%

4-chlorophenyl methyl sulfide (123-09-1) → (R)-1-chloro-4-(methylsulfinyl)benzene (28227-63-6)

Guidance literature:

With unspecific peroxygenase from agrocybe aegerita; dihydrogen peroxide; In aq. phosphate buffer; acetonitrile; at 25 ℃; for 0.333333h; pH=7; Reagent/catalyst; Solvent; enantioselective reaction; Catalytic behavior; Enzymatic reaction;

DOI:10.1002/ejoc.201701390

Reference yield: 91.0%

4-chlorophenyl methyl sulfide (123-09-1) → (S)-4-chlorophenyl methyl sulfoxide (934-73-6,28227-63-6,56487-58-2,112456-62-9)

Guidance literature:

With titanium(IV) isopropylate; Cumene hydroperoxide; (R,R)-CH₃(CH₂)6OOCCH(OH)CH(OH)COO-polyethylene glycol-OMe; In dichloromethane; at -20 ℃; for 16h;

DOI:10.1016/j.tetlet.2007.09.169

Reference yield: 85.0%

4-chlorophenyl methyl sulfide (123-09-1) → (S)-4-chlorophenyl methyl sulfoxide (934-73-6,28227-63-6,56487-58-2,112456-62-9) + (R)-1-chloro-4-(methylsulfinyl)benzene (28227-63-6)

Guidance literature:

With MoO(O₂)2(H₂O); C₁₅H₂₄N₂O₄; dihydrogen peroxide; tetraphenylphosphonium bromide; In chloroform; water; at 0 ℃; for 1h; enantioselective reaction;

DOI:10.3390/molecules23071595

upstream raw materials:

methyl magnesium iodide

menthyl (S_c,S_c)-p-chlorobenzenesulfinate

4-chlorophenyl methyl sulfide

methylmagnesium bromide

Downstream raw materials:

10-dicyclohexylsulfamoyl-D-isobornyl (S)(-)-4-chlorophenylsulfinylacetate

10-dicyclohexylsulfamoyl-D-isobornyl (R)(+)-4-chlorophenylsulfinylacetate

(R)-(+)-Methyl <(4-chlorophenyl)sulfinyl>acetate

Refernces

• 1、 Liu, Yafei,Ni, Ye,Wei, Shiyu,Xu, Guochao,Zhou, Jieyu. "Two enantiocomplementary Baeyer-Villiger monooxygenases newly identified for asymmetric oxyfunctionalization of thioether". . . Retrieved 2021/08/19.
• 2、 Heine, Thomas,Scholtissek, Anika,Hofmann, Sarah,Koch, Rainhard,Tischler, Dirk. "Accessing Enantiopure Epoxides and Sulfoxides: Related Flavin-Dependent Monooxygenases Provide Reversed Enantioselectivity". . p. 199 - 209. Retrieved 2019/11/13.