299464-13-4

Basic information

• Product Name: 2-(2,4-dichlorophenyl)-1,3-dithiane
• Synonyms: 2-(2,4-dichlorophenyl)-1,3-dithiane
• CAS NO: 299464-13-4
• Molecular Weight: 265.227
• Mol File: 299464-13-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-(2,4-dichlorophenyl)-1,3-dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-dichlorophenyl)-1,3-dithiane(299464-13-4)
• EPA Substance Registry System: 2-(2,4-dichlorophenyl)-1,3-dithiane(299464-13-4)

Safety Data

• Hazardous Substances Data: 299464-13-4(Hazardous Substances Data)

Upstream product

• 109-80-8 1.3-propanedithiol 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 57529-04-1 2-chloro-1,3-dithiane 

Relevant articles and documents

Fe-catalyzed direct dithioacetalization of aldehydes with 2-chloro-1,3-dithiane

Present methods to synthesize 1,3-dithiane molecules require either harsh reaction conditions or highly specialized reagents. We have developed a catalytic dithioacetalization process that directly gains access to the corresponding 1,3-dithianes using aldehydes and 2-chloro-1,3-dithiane in a highly efficient manner. This methodology is beneficial due to mildness of the reaction conditions, and the dithioacetaliation process results in good to excellent yields by using 15 mol % of an iron catalyst.

The directing group wins over acidity: kinetically controlled regioselective lithiation for functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives

Regioselective lithiation followed by functionalization of 2-(2,4-dihalophenyl)-1,3-dithiane derivatives with different electrophiles was achieved in good to excellent yields. When the title compound is treated with n-butyl lithium, lithiation occurs selectively at the aromatic carbon having less acidic proton despite the presence of thermodynamically more acidic 1,3-dithiane proton in the same molecule. Computationally calculated pKa values of the available reactive site protons and the experimental results suggest that the regioselective lithiation in 2-(2,4-dihalophenyl)-1,3-dithiane derivatives is not governed by thermodynamic acidity rather exclusively dictated by the kinetic removal of protons due to cooperative coordination (complex induced proximity effect, CIPE) and inductive effects of the 1,3-dihalo substituents present in the aromatic ring. By employing this regioselective functionalization, diverse 1,2,3,4-tetra-substituted aromatic compounds were prepared with ease.

Chemoselective dithioacetalization of carbonyl compounds using magnesium hydrogensulfate as efficient heterogeneous catalyst

Carbonyl compounds have been successfully converted into their corresponding dithiolanes and dithianes derivatives with 1,2-ethanedithiol and 1,3-propanedithiol in excellent yield at room temperature and short reaction times using a catalytic amount of ma