147923-23-7

Usage

Uses

Used in Materials Science:
<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is used as a component in the development of new materials for various industrial applications due to its unique molecular structure and metal-coordinating properties.
Used in Pharmaceutical Industry:
<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is used as a potential therapeutic agent for targeting specific diseases, leveraging its fungicidal and bactericidal properties to combat infections.
Used in Agrochemicals:
<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is used as a fungicide and bactericide in the agricultural sector to protect crops from diseases and enhance yield.
Used in Coordination Chemistry and Catalysis:
<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is used as a ligand in coordination chemistry and catalysis, taking advantage of its ability to coordinate with metal ions to facilitate chemical reactions.

Upstream product

• 55441-97-9 <1,1'-Binaphthalene>-2,2'-diyl O,O-bis(N,N-dimethylthiocarbamate) 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 

Downstream Products

• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 188-57-8 Dinaphtho<2,1-c:1',2'-e><1,2>dithiane 
• 188-57-8 Dinaphtho<2,1-c:1',2'-e><1,2>dithiane 
• 55441-99-1 (S)-[1,1'-binaphthalene]-2,2'-dithiol 
• 55441-99-1 (R)-1,1′-binaphthalene-2,2′-dithiol 
• 194-65-0 1,1'-binaphthothiophene 
• 188-57-8 (R)-(-)-dinaphtho<2,1-c:1',2'-e><1,2>dithiin 

Relevant academic research and scientific papers

Practical synthetic approach to chiral sulfonimides (CSIs) - Chiral bronsted acids for organocatalysis

A general approach to the synthesis of optically pure 3,3'diaryl chiral sulfonimides (CSIs) from racemic BINOL has been developed. ortho-Lithiation is directed by the sulfonyl groups, and the resulting dihalides serve as the common precursors for the aryl-substituted CSIs.

Photocatalyzed E→Z Contra-thermodynamic Isomerization of Vinyl Boronates with Binaphthol

The photocatalytic contra-thermodynamic E→Z isomerization of vinyl boronates by using a binaphthol catalyst is disclosed. The reaction, based on the transient formation of a suitable chromophore with a BINOL derivative as the catalyst, allowed geometrical isomerization in good-to-excellent Z/E ratio and excellent-to-quantitative yields. The mechanism of this E→Z contra-thermodynamic isomerization was studied, and the formation of a transient chromophore species is suggested.

Synthesis of structurally modified atropisomeric biaryl dithiols. Observations on the Newman-Kwart rearrangement

The preparation of a number of biaryldithiols from biaryldiols is discussed. A key reaction is the Newman-Kwart thermorearrangement of bisthiocarbamates and crucial variables of temperature and reaction time have been identified. Alternative approaches to 3,3'-disubstituted dithiols via ortho metallation are presented. The benefit of using such disubstituted compounds is illustrated with representative examples of the stereochemical features of the derived carbanions in reactions with prochiral electrophiles.

Conformational polymorphism and thermorearrangement of 2,2′-bis-O-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. A facile synthesis of 1,1′-binaphthalene-2,2′-dithiol

The title compound was found to exhibit conformational polymorphism which greatly influenced the efficiency of the thermorearrangement to 2,2′-bis-S-(N,N-dimethylthiocarbamato)-1,1′-binaphthalene. Recognition of this phenomenon has allowed a reproducible synthesis of 1,1′-binaphthalene-2,2′ dithiol.

Preparation of Enantiomerically Pure 1,1'-Binaphthalene-2,2'-diol and 1,1'-Binaphthalene-2,2'-dithiol

A practical preparation of enantiomerically pure 1,1'-binaphthalene-2,2'-diol (1) and 1,1'-binaphthalene-2,2'-dithiol (2) is reported.Enantiopure 2 is obtained from enantiopure 1 via Newman-Kwart rearrangement of the thiocarbamoyl derivative 5 under controlled reaction conditions.The enantiopure starting diol 1 was obtained by a simple and inexpensive method engaging condensation of thiophosphoryl chloride and (S)-(-)-α-methylbenzylamine in pyridine and reaction of the resulting phosphoramidate 3 with racemic binaphthol 1 to give quantitatively a 1:1 mixture of diasteroisomers 4 that were cleanly separated by a single recrystallization from a chloroform-ethanol mixture in very high yield.The procedures can be scaled up easily.

Enantioselective oxidation of thioethers. A route to the resolution of -2,2'-dithiol

A route to the resolution of racemic -2,2'-dithiol 2 is described, involving the transformation of 2 into a series of dithioethers.The latter are subjected to asymmetric oxidation to monosulfoxides by a procedure developed in our laboratory.For some of the thioethers examined the oxidation is highly diastereo- and/or enantioselective.The resolved 2 is then obtained from the optically pure monosulfoxides either by oxidation to the bis-sulfoxides followed by a Pummerer reaction or by a deoxygenation to the dithioether and subsequent reduction.In both cases enantiomerically pure 2 (e.e. > 98percent) was obtained.Keywords: enantioselective oxidation / optical resolution / thioethers / -2,2'-dithiol