188-57-8

Basic information

• Product Name: Dinaphtho<2,1-c:1',2'-e><1,2>dithiane
• CAS NO: 188-57-8
• Molecular Weight: 316.447
• Mol File: 188-57-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Dinaphtho<2,1-c:1',2'-e><1,2>dithiane(CAS DataBase Reference)
• NIST Chemistry Reference: Dinaphtho<2,1-c:1',2'-e><1,2>dithiane(188-57-8)
• EPA Substance Registry System: Dinaphtho<2,1-c:1',2'-e><1,2>dithiane(188-57-8)

Safety Data

• Hazardous Substances Data: 188-57-8(Hazardous Substances Data)

Upstream product

• 124414-33-1 Dinaphtho<2,1-d:1',2'-f><1,4>dithiocane S-oxide 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 147923-23-7 <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 124414-29-5 Dinaphtho<2,1-d:1',2'-g><1,4>dithiocane 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio) 
• 91-60-1 2-Naphthalenethiol 
• 602-09-5 1,1'-bi-2-naphthol 
• 162825-40-3 (S)-4<(1''R,2''S,3''R,4''R)-1'',2'',3'',4'',5''-pentamethoxypentyl>-dinaphtho<2,1-d:1',2'-f><1,3>dithipin 
• 74866-28-7 2,2'-dibromo-1,1'-binaphthyl 
• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 194-65-0 1,1'-binaphthothiophene 

Downstream Products

• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 55441-99-1 (S)-[1,1'-binaphthalene]-2,2'-dithiol 
• 55441-99-1 (R)-1,1′-binaphthalene-2,2′-dithiol 

Relevant articles and documents

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.

Resolution of (1,1'-binaphthalene)-2,2'-dithiol via diastereoisomeric dithioacetals derived from D-glucose

The efficient resolution of (1,1'-binaphthalene)-2,2'-dithiol has been achieved by the preparation and separation of the chiral diastereoisomeric binaphthalene dithioacetals derived from 2,3,4,5,6-penta-O-methyl-D-glucose followed by transthioacetalization with ethane-1,2-dithiol.

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