147923-23-7

Basic information

• Product Name: <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate)
• CAS NO: 147923-23-7
• Molecular Weight: 460.621
• Mol File: 147923-23-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate)(CAS DataBase Reference)
• NIST Chemistry Reference: <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate)(147923-23-7)
• EPA Substance Registry System: <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate)(147923-23-7)

Safety Data

• Hazardous Substances Data: 147923-23-7(Hazardous Substances Data)

Usage

Description

<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is a chemical compound with the molecular formula C30H28N2S2, belonging to the dithiocarbamate class. It is derived from the rigid and chiral 1,1'-binaphthalene molecule and features an S,S-bis(N,N-dimethylthiocarbamate) group, which is known for its metal-coordinating capabilities. <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) is recognized for its fungicidal and bactericidal properties, and due to its unique structure and properties, it holds potential applications in various fields such as materials science, pharmaceuticals, and agrochemicals.

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

• 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 
• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 

Relevant articles and documents

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.

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.

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.