2-(Methylthio)benzaldehyde

Base Information

• Chemical Name: 2-(Methylthio)benzaldehyde
• CAS No.: 7022-45-9
• Molecular Formula: C8H8OS
• Molecular Weight: 152.217
• Hs Code.: 2930909090
• NSC Number: 144623
• DSSTox Substance ID: DTXSID70301596
• Nikkaji Number: J1.332.180I
• Wikidata: Q72491343
• Mol file: 7022-45-9.mol

Synonyms:2-(Methylthio)benzaldehyde;7022-45-9;2-(methylthio) Benzaldehyde;2-methylsulfanylbenzaldehyde;2-(methylsulfanyl)benzaldehyde;benzaldehyde, 2-(methylthio)-;Benzaldehyde,2-(methylthio)-;NSC144623;2-Methylthio Benzaldehyde;2-(methylthio)-benzaldehyde;2-methylmercapto-benzaldehyde;2-methylsulfanyl-benzaldehyde;SCHEMBL173014;DTXSID70301596;XIOBUABQJIVPCQ-UHFFFAOYSA-N;2-(Methylthio)benzaldehyde, 90%;STR05859;2-(methylsulfanyl)benzenecarbaldehyde;MFCD00196822;AKOS009157429;NSC-144623;AC-16446;CS-0006413;FT-0636335;M2094;T72851;J-506484

Chemical Property of 2-(Methylthio)benzaldehyde

Chemical Property:

• Refractive Index: n20/D 1.633(lit.)
• Boiling Point: 248.6 °C at 760 mmHg
• Flash Point: 117.4 °C
• PSA: 42.37000
• Density: 1.13 g/cm³
• LogP: 2.22100
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 152.02958605
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

97% ^*data from raw suppliers

2-(Methylthio)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=CC=CC=C1C=O
• Uses: 2-(METHYLTHIO)BENZALDEHYDE is a useful research chemical.

Technology Process of 2-(Methylthio)benzaldehyde

There total 28 articles about 2-(Methylthio)benzaldehyde 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: 94.0%

2-(methylthio)benzyl alcohol (33384-77-9) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Guidance literature:

With dimethylsulfide; N-succinimide; triethylamine; In toluene;

DOI:10.1021/ja00357a021

Reference yield: 93.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + ortho-bromobenzaldehyde (6630-33-7) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; at 130 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.07.047

Reference yield: 86.0%

2-chloro-benzaldehyde (89-98-5) + sodium thiomethoxide (5188-07-8) → 2-(methylsulfanyl)benzaldehyde (7022-45-9)

Guidance literature:

In N,N,N,N,N,N-hexamethylphosphoric triamide; for 5h; Heating;

DOI:10.1248/cpb.34.1589

upstream raw materials:

N'-p-Toluolsulfonyl-N-<2-methylmercapto-benzoyl>-hydrazin

2-(methylthio)benzyl alcohol

2-chloro-benzaldehyde

sodium thiomethoxide

Downstream raw materials:

2-Nitro-1-(2-methylmercapto-phenyl)-propen-⁽¹⁾

1-(2-Methylthiophenyl)-2-(4-nitrophenyl)ethanol

2-Methylmercpto-benzaldoxim

Refernces

Intermolecular hydroacylation: High activity rhodium catalysts containing small-bite-angle diphosphine ligands

10.1021/ja211649a

The research aims to develop highly efficient rhodium catalysts for the intermolecular hydroacylation of unactivated alkenes and alkynes with β-S-substituted aldehydes. The study focuses on using small-bite-angle diphosphine ligands, such as [Rh(C6H5F)(R2PCH2PR2)][BArF4] (where R, R′ = tBu or Cy), to create catalysts that are both bench-stable and highly active. The key chemicals used include various diphosphine ligands, fluorobenzene, and β-S-substituted aldehydes like 2-(methylthio)benzaldehyde. The researchers synthesized several catalyst precursors and characterized intermediates like acyl hydride complexes and decarbonylation products using NMR spectroscopy and X-ray crystallography. The study concludes that by carefully selecting solvents and optimizing catalyst/substrate concentrations, decarbonylation can be minimized, and very low catalyst loadings (0.1 mol %) with turnover frequencies exceeding 300 h?1 can be achieved. The developed catalysts are highly efficient, allowing for the hydroacylation of a broad range of substrates, including challenging ones like disubstituted alkenes and enol ethers. The findings suggest that these catalysts could be further developed for enantioselective applications and for reactions that do not require β-tethered aldehydes.