6522-21-0

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Dichloro-9-thiabicyclo(3.3.1)nonane is used as a key intermediate in the synthesis of new drugs. Its unique structure allows for the development of pharmaceutical compounds with specific therapeutic properties, contributing to the advancement of medicine.
Used in Agrochemical Industry:
In the agrochemical sector, 2,6-Dichloro-9-thiabicyclo(3.3.1)nonane serves as a precursor in the production of pesticides. Its incorporation into these compounds can enhance their effectiveness in controlling pests and diseases, thereby improving crop yields and food security.
Used in Organic Synthesis:
2,6-Dichloro-9-thiabicyclo(3.3.1)nonane is utilized as a building block in organic synthesis for creating a wide range of complex molecules. Its structural features make it a valuable component in the development of new chemical entities with potential applications in various industries.

InChI:InChI=1/C8H12Cl2S/c9-5-1-3-7-6(10)2-4-8(5)11-7/h5-8H,1-4H2

Upstream product

• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 5961-98-8 thiocyanatochloride 

Downstream Products

• 281-15-2 9-thia-bicyclo[3.3.1]nonane 
• 75937-76-7 2-isobutyl-9-thiabicyclo<3.3.1>nonane 
• 75937-77-8 2,6-diisobutyl-9-thiabicyclo<3.3.1>nonane 

Relevant academic research and scientific papers

Thia-, Aza-, and selena[3.3.1]bicyclononane dichlorides: Rates vs internal nucleophile in anchimeric assistance

Sulfur-, selenium-, and nitrogen-containing compounds bearing leaving groups in the β-position undergo facile substitution chemistry enabled by anchimeric assistance. Here we provide direct comparisons between such systems in the rigid bicyclo[3.3.1]nonane framework easily derived from 1,5-cyclooctadiene. For a series of dichloride electrophiles of this type, the relative reactivities were found to be Se ? (alkyl)N > S ≥ (propargyl)N > (phenyl)N, with the reaction rates at the two extremes differing by more than 3 orders of magnitude. For the N-alkyl case, substitution rates were largely independent of the trapping nucleophile but were strongly dependent on solvent, showing that the process is controlled by the formation of the high-energy three-membered cationic intermediate.

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane: Multigram display of azide and cyanide components on a versatile scaffold

2,6-Dichloro-9-thiabicyclo[3.3.1]nonane, easily available by an improved condensation of sulfur dichloride, sulfuryl chloride, and 1,5-cyclooctadiene, is a well-behaved scaffold for the nucleophilic substitution of azides and cyanides via neighboring-group participation by the sulfur atom. The products are isolated in high yields with purity >95% by simple extraction and washing protocols.

Transannular Reactions of Cycloalkenes, Cycloalkadienes and Cycloalkatrienes. VIII. The Electrophilic Addition of Pseudohalogenes to Cycloocta-1(Z),5(Z)-diene

The reaction of cycloocta-1(Z),5(Z)-diene 5 with chlorothiocyanate is described.The main process is the normal anti-addition to produce trans-5-chloro-6-thiocyanato-(Z)-cyclooctene 6.In addition 2,6-dichloro-9-thiabicyclononane 7 and 2,6-dithiocyanato-9-thiabicyclononane 8 are obtained as products of a transannular reaction.