74925-48-7

Usage

Molecular Structure

Contains a 1H-indene ring with two chlorine atoms attached at positions 1 and 2, and a hydrogen atom at position 3.

Physical State

Colorless liquid.

Uses

Mainly used as an intermediate in the production of various compounds, including pharmaceuticals, agrochemicals, and polymers. Utilized in the synthesis of organic chemicals and as a solvent for chemical reactions. Potential applications in material science and as a building block for specialty chemicals.

Importance

Versatile reactivity and usefulness in various industrial processes make it an important compound with a wide range of potential applications.

InChI:InChI=1/C9H8Cl2/c10-8-5-6-3-1-2-4-7(6)9(8)11/h1-4,8-9H,5H2

Upstream product

• 60-29-7 diethyl ether 
• 95-13-6 1-indene 
• 10026-13-8 phosphorus pentachloride 
• 19598-01-7 trans-2-chloroindan-1-ol 
• 7719-09-7 thionyl chloride 
• 19598-01-7 cis-2-chloroindan-1-ol 

Downstream Products

• 18427-72-0 2-chloro-1H-indene 
• 19598-01-7 cis-2-chloroindan-1-ol 
• 19598-01-7 trans-2-chloroindan-1-ol 
• 861008-91-5 4-chloro-2-inden-3-yl-phenol 
• 83-33-0 inden-1-one 
• 4370-02-9 trans-indane-1,2-diol 

Relevant academic research and scientific papers

Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

The use of a new class of unsymmetrical cinchona-alkaloid-based, phthalazine-bridged organocatalysts enabled the highly enantioselective dichlorination of unfunctionalized alkenes. In combination with the electrophilic chlorinating agent 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) and triethylsilyl chloride (TES-Cl) as the source of nucleophilic chloride, 1-aryl-2-alkyl alkenes were dichlorinated with enantioselectivities of up to 94:6 er. Initial mechanistic investigations suggest that no free chlorine is formed, and by replacement of the chloride by fluoride, enantioselective chlorofluorinations of alkenes are possible.

Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources

We report a Mn-catalyzed electrochemical dichlorination of alkenes with MgCl2 as the chlorine source. This method provides operationally simple, sustainable, and efficient access to a variety of vicinally dichlorinated compounds. In particular, alkenes with oxidatively labile functional groups, such as alcohols, aldehydes, sulfides, and amines, were transformed into the desired vicinal dichlorides with high chemoselectivity. Mechanistic data are consistent with metal-mediated Cl atom transfer as the predominant pathway enabling dual C-Cl bond formation and contradict an alternative pathway involving electrochemical evolution of chlorine gas followed by Cl2-mediated electrophilic dichlorination.