(1-Chloroethanesulfinyl)benzene

Base Information

• Chemical Name: (1-Chloroethanesulfinyl)benzene
• CAS No.: 26910-40-7
• Molecular Formula: C8H9ClOS
• Molecular Weight: 188.678
• DSSTox Substance ID: DTXSID30495627
• Nikkaji Number: J376.353F
• Mol file: 26910-40-7.mol

Synonyms:26910-40-7;1-chloroethylsulfinylbenzene;Benzene, [(1-chloroethyl)sulfinyl]-;alpha-Chloroethyl Phenyl Sulfoxide;((1-Chloroethyl)sulfinyl)benzene;[(1-chloroethyl)sulfinyl]benzene;(1-Chloroethanesulfinyl)benzene;starbld0033006;1-chloroethylsulfinyl-benzene;SCHEMBL8107422;DTXSID30495627;AKOS030255166

Chemical Property of (1-Chloroethanesulfinyl)benzene

Chemical Property:

• Boiling Point: 311.2±25.0 °C(Predicted)
• PSA: 36.28000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 3.24470
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.0062638
• Heavy Atom Count: 11
• Complexity: 143

Purity/Quality:

α-ChloroethylPhenylSulfoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(S(=O)C1=CC=CC=C1)Cl
• Uses: α-Chloroethyl Phenyl Sulfoxide is an intermediate in synthesizing 3-Deoxy-3-acetylabiraterone-3-ene (D232060), which is an impurity of Abiraterone (A108490), a steroidal cytochrome P 450 17α-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer.

Technology Process of (1-Chloroethanesulfinyl)benzene

There total 5 articles about (1-Chloroethanesulfinyl)benzene 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%

chloromethyl phenyl sulfoxide (7205-94-9) + methyl iodide (74-88-4) → 1-chloroethyl phenyl sulfoxide (26910-40-7)

Guidance literature:

chloromethyl phenyl sulfoxide; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.201801614

Reference yield: 88.0%

Ethyl phenyl sulfide (622-38-8) → 1-chloroethyl phenyl sulfoxide (26910-40-7)

Guidance literature:

With sulfuryl dichloride; silver nitrate; In acetonitrile; at 0 - 25 ℃; for 1.33333h;

DOI:10.1055/s-1993-25831

Reference yield: 75.0%

chloromethyl phenyl sulfoxide (7205-94-9) + methyl iodide (74-88-4) → 1-chloroethyl phenyl sulfoxide (26910-40-7) + (1-chloro-1-methyl)ethyl phenyl sulfoxide (26910-41-8)

Guidance literature:

chloromethyl phenyl sulfoxide; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

methyl iodide; In tetrahydrofuran; hexane; at -78 - -10 ℃;

DOI:10.1021/tx9901433

upstream raw materials:

ethylphenylsulfoxide

Ethyl phenyl sulfide

chloromethyl phenyl sulfoxide

methyl iodide

Downstream raw materials:

2-Benzenesulfinyl-2-methyl-3-phenethyl-oxirane

2'-Methyl-2'-(phenylsulfinyl)spiro

1-(1-Benzenesulfinyl-1-chloro-ethyl)-cycloheptanol

1-(1-chloroethyl)phenyl sulfone

Refernces

• 1、 Monticelli, Serena,Urban, Ernst,Langer, Thierry,Holzer, Wolfgang,Pace, Vittorio. "A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids". supporting information. p. 1001 - 1006. Retrieved 2019/01/30.
• 2、 Mutterer,Gimenez Arnau,Karlberg,Lepoittevin. "Synthesis and allergenic potential of a 15-hydroperoxyabietic acid-like model: Trapping of radical intermediates". . p. 1028 - 1036. Retrieved 2007/10/03.