4-Methoxybenzenethiol

Base Information

• Chemical Name: 4-Methoxybenzenethiol
• CAS No.: 696-63-9
• Molecular Formula: C7H8OS
• Molecular Weight: 140.206
• Hs Code.: 29309090
• European Community (EC) Number: 211-799-2
• NSC Number: 100727
• UNII: 68N68LMU0G
• DSSTox Substance ID: DTXSID60219873
• Nikkaji Number: J54.510D
• Wikidata: Q72486214
• ChEMBL ID: CHEMBL119636
• Mol file: 696-63-9.mol

Synonyms:4-Methoxybenzenethiol;4-Methoxythiophenol;696-63-9;Benzenethiol, 4-methoxy-;p-Methoxybenzenethiol;BENZENETHIOL, p-METHOXY-;4-methoxybenzene-1-thiol;4-Methoxy thiophenol;4-Methoxy-benzenethiol;4-Mercaptoanisole;p-methoxythiophenol;NSC 100727;para-Methoxybenzenethiol;EINECS 211-799-2;BRN 1446910;68N68LMU0G;NSC-100727;4-mercaptoanisol;4methoxythiophenol;4methoxybenzenethiol;4-methoxybenzenthiol;4-methoxyphenylthiol;p-Methoxy thiophenol;4-methoxy-thiophenol;NSC100727;4-methoxylbenzenethiol;4-methoxy benzenethiol;4-methoxybenzene thiol;P-MERCAPTOANISOLE;4-methoxy-benzene thiol;4-(methyloxy)benzenethiol;4-methoxy-1-benzenethiol;P-METHOXYPHENYLTHIOL;WLN: SHR DO1;4-Methoxythiophenol, 97%;UNII-68N68LMU0G;SCHEMBL50514;CHEMBL119636;METHOXYBENZENETHIOL, 4-;P-METHOXYPHENYL MERCAPTAN;4-METHOXYPHENYL MERCAPTAN;NIFAOMSJMGEFTQ-UHFFFAOYSA-;DTXSID60219873;CS-D1129;STR00751;BBL027485;MFCD00004849;STL374080;AKOS005203301;AC-7112;LS-32193;FT-0618859;M1333;4-Methoxythiophenol, purum, >=98.0% (GC);EN300-11815;D78094;A836591;W-104608;F0001-1809;QU5

Chemical Property of 4-Methoxybenzenethiol

Chemical Property:

• Appearance/Colour: Colorless light yellow liquid
• Vapor Pressure: 0.133mmHg at 25°C
• Melting Point: 291.7-295.8 °C (decomp)
• Refractive Index: n20/D 1.5831(lit.)
• Boiling Point: 224.9 °C at 760 mmHg
• PKA: 6.76±0.10(Predicted)
• Flash Point: 89.8 °C
• PSA: 48.03000
• Density: 1.112 g/cm³
• LogP: 1.98390
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Stench
• Solubility.: Not miscible or difficult to mix.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 140.02958605
• Heavy Atom Count: 9
• Complexity: 77

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxybenzenethiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)S
• General Description: 4-METHOXYBENZENETHIOL (also known as p-mercaptoanisole or 4-methoxythiophenol) is a thiophenol derivative featuring a methoxy group para to the thiol functionality. It serves as a nucleophilic reagent in thia-Michael addition reactions, particularly in the presence of nickel-based catalysts, enabling efficient C-S bond formation with α,β-enones under mild conditions. Its utility in such reactions highlights its relevance in synthetic organic chemistry, especially for pharmaceutical and natural product synthesis. **Returned paragraph:** 4-METHOXYBENZENETHIOL is a thiol compound used as a nucleophile in thia-Michael additions, demonstrating effectiveness in C-S bond-forming reactions with α,β-enones when catalyzed by nickel complexes. Its methoxy-substituted aromatic structure enhances its reactivity in synthetic applications, particularly in pharmaceutical contexts. *(Note: The abstract did not provide specific properties or broader applications of 4-METHOXYBENZENETHIOL beyond its role in the studied reaction, so the description focuses on its functional utility.)*

Technology Process of 4-Methoxybenzenethiol

There total 74 articles about 4-Methoxybenzenethiol 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: 100.0%

1-methoxy-4-[[(Z)-2-[(4-methylphenyl)sulfonyl]vinyl]sulfanyl]benzene (243671-60-5) → 4-Methoxybenzenethiol (696-63-9)

Guidance literature:

With pyrrolidine; In acetonitrile; at 20 ℃; for 31h;

DOI:10.1021/jo990308c

Reference yield: 99.0%

4,4'-dimethoxyphenyl disulfide (5335-87-5) → 4-Methoxybenzenethiol (696-63-9)

Guidance literature:

With hydrogenchloride; diphenylphosphinopolystyrene; In tetrahydrofuran; for 6h; Heating;

DOI:10.1021/jo00188a028

Reference yield: 96.0%

sodium 4-methoxybenzenesulfinate (6462-50-6) → 4-Methoxybenzenethiol (696-63-9)

Guidance literature:

With hydrogenchloride; tin; In water; for 24h; Heating;

DOI:10.1081/SCC-100104044

upstream raw materials:

p-methoxybenzenediazonium

4-methoxybenzenesulfinic acid

methoxybenzene

4-methoxy-aniline

Downstream raw materials:

1-[(4-methoxy-phenylsulfanyl)-methyl]-piperidine

(Z)-1,2-bis(p-methoxyphenylsulfanyl)ethylene

trans-1,2-bis-(4-methoxy-phenylsulfanyl)-ethene

β-(4-methoxyphenylmercapto)propionic acid

Refernces

Highly efficient proline ester-based nickel catalysts for Michael addition of thiophenols to α,β-enones

10.1002/jccs.201200386

The research focuses on the development of highly efficient nickel catalysts based on proline esters for the thia-Michael addition of thiophenols to α,β-enones. The purpose of this study was to create catalysts that could facilitate this C-S bond forming reaction under mild conditions with high yields, which is significant for the synthesis of pharmaceuticals and natural products. The researchers synthesized two nickel complexes, Ni(BMPP)(CH3CN)2 (1) and Ni(BPPP)(CH3CN)2 (2), using N3O2 pentadentate ligands, BMPP and BPPP. The conclusions drawn from the study were that both complexes 1 and 2 were effective for the thia-Michael addition at ambient temperature, with catalyst 1 being particularly efficient, requiring only 0.5 mol% loading for the reaction. The chemicals used in the process included 4-methoxythiophenol, 2-cyclohexenone, BMPP, BPPP, Ni(CH3CN)62, NaBPh4, and various other reagents and solvents for synthesis and characterization.