4-pyridylphenyl methanethiosulfonate

Base Information

• Chemical Name: 4-pyridylphenyl methanethiosulfonate
• CAS No.: 917572-05-5
• Molecular Formula: C₁₂H₁₁NO₂S₂
• Molecular Weight: 265.357
• Mol file: 917572-05-5.mol

Synonyms:4-pyridylphenyl methanethiosulfonate

Chemical Property of 4-pyridylphenyl methanethiosulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-pyridylphenyl methanethiosulfonate

There total 5 articles about 4-pyridylphenyl methanethiosulfonate 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: 71.4%

4-(4-pyridyl)phenyl disulfide (917572-04-4) + sodium methanethiosulfonate (1950-85-2) → 4-pyridylphenyl methanethiosulfonate (917572-05-5)

Guidance literature:

With silver nitrate; In water; acetone; for 1h; Heating;

DOI:10.1016/j.bmc.2006.09.058

Reference yield:

(4-bromophenyl)thioanisole (104-95-0) → 4-pyridylphenyl methanethiosulfonate (917572-05-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: triisopropoxy borate / tetrahydrofuran; hexane / -78 - 20 °C

1.3: water / tetrahydrofuran; hexane

2.1: 63 percent / KOH; Bu₄NBr / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H₂O / 48 h / 80 °C

3.1: 81.1 percent / t-BuSNa / dimethylformamide / 5 h / Heating

4.1: 50 percent / vanadyl acetylacetonate; tert-butylhydroperoxide / CH₂Cl₂; decane / -15 - 20 °C

5.1: 71.4 percent / silver nitrate / acetone; H₂O / 1 h / Heating

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; vanadyl acetylacetonate; tetrabutylammomium bromide; sodium tert-butyl thiolate; silver nitrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; decane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2.1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.09.058

Reference yield:

(4-thiomethoxyphenyl)boronic acid (98546-51-1) → 4-pyridylphenyl methanethiosulfonate (917572-05-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / KOH; Bu₄NBr / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H₂O / 48 h / 80 °C

2: 81.1 percent / t-BuSNa / dimethylformamide / 5 h / Heating

3: 50 percent / vanadyl acetylacetonate; tert-butylhydroperoxide / CH₂Cl₂; decane / -15 - 20 °C

4: 71.4 percent / silver nitrate / acetone; H₂O / 1 h / Heating

With tert.-butylhydroperoxide; potassium hydroxide; vanadyl acetylacetonate; tetrabutylammomium bromide; sodium tert-butyl thiolate; silver nitrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,2-dimethoxyethane; decane; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Suzuki coupling;

DOI:10.1016/j.bmc.2006.09.058

upstream raw materials:

4-(4-pyridyl)phenyl disulfide

sodium methanethiosulfonate

4-(4-(methylthio)phenyl)pyridine

(4-bromophenyl)thioanisole

Refernces