102555-71-5

Basic information

• Product Name: (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL
• Synonyms: 1-(2-SULFANYLNAPHTHALEN-1-YL)NAPHTHALENE-2-THIOL;(+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL;()-1.1''-BINAPHTHALENE-2,2''-DITHIO
• CAS NO: 102555-71-5
• Molecular Formula: C₂₀H₁₄S₂
• Molecular Weight: 318.46
• Mol File: 102555-71-5.mol

Chemical Properties

• Boiling Point: 495 °C at 760 mmHg
• Flash Point: 230.1 °C
• Appearance: /
• Density: 1.283 g/cm³
• CAS DataBase Reference: (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL(102555-71-5)
• EPA Substance Registry System: (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL(102555-71-5)

Safety Data

• Hazardous Substances Data: 102555-71-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL is used as a key intermediate for the synthesis of chiral, atropisomeric organosulfur compounds. These compounds are essential in the development of pharmaceuticals, particularly in the creation of enantiomerically pure drugs. The unique structure of (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL allows for the formation of chiral centers, which are crucial for the biological activity and selectivity of the resulting compounds.
Used in Chemical Synthesis:
(+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL is used as a versatile building block in the synthesis of various organic compounds, including ligands, catalysts, and other chiral molecules. Its binaphthyl core and thiol groups provide a robust framework for further functionalization and modification, enabling the development of new materials and compounds with tailored properties.
Used in Materials Science:
(+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL can be employed in the development of novel materials with specific optical, electronic, or mechanical properties. The chiral nature of the molecule and its ability to form atropisomeric organosulfur compounds make it a promising candidate for applications in the field of materials science, such as in the design of chiral liquid crystals, sensors, or optoelectronic devices.

Upstream product

• 157367-47-0 pentanethioic acid S,S'-<(1,1'-binaphthalene)-2,2'-diyl> ester 
• 602-09-5 1,1'-bi-2-naphthol 
• 188-57-8 (R)-(-)-dinaphtho<2,1-c:1',2'-e><1,2>dithiin 
• 120577-40-4 C₂₉H₂₄O₅S₂ 
• 147923-23-7 <1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) 
• 120546-24-9 (+/-)-7,10-Dithiadinaphtho<2,1-d:1',2'-f>cyclooctene 7,7,10,10-tetraoxide 
• 194-65-0 1,1'-binaphthothiophene 
• 124414-32-0 2-Methanesulfinyl-2'-methylsulfanyl-[1,1']binaphthalenyl 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 102555-71-5 1,1'-binaphthalene-2,2'-dithiol 
• 124414-35-3 2,2'-Bis-methanesulfinyl-[1,1']binaphthalenyl 
• 124414-32-0 (2-Methylsulfinyl-2'-methylthio)<1,1'-binaphthalene> 
• 124414-28-4 (2,2'-Dimethylthio)<1,1'-binaphthalene> 
• 188-57-8 Dinaphtho<2,1-c:1',2'-e><1,2>dithiane 

Downstream Products

• 55441-99-1 (+)-<1,1'-binaphthalene>-2,2'-dithiol 
• 55441-99-1 (-)-<1,1'-binaphthalene>-2,2'-dithiol 
• 122361-59-5 (Ra)-1,1'-binaphthyl-2,2'-disulfonic acid 

Relevant articles and documents

Synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2, 2′-disulfonic acids

A convenient synthesis of chiral 3,3′-disubstituted 1,1′-binaphthyl-2,2′-disulfonic acids (BINSA, 1) was developed. The key was directed ortho-lithiation of BINSA methyl ester 2 with n-BuLi and subsequent reaction with an electrophile. Electrophiles such as Br2, I2, Me3SiOTf, and i-PrOB(Pin) reacted smoothly with 3,3′-dilithiated BINSA methyl ester, and the corresponding 3,3′-dihalo-, 3,3′-bis(trimethylsilyl)-, and 3,3′-diboryl- BINSA derivatives were obtained in yields of 21-78%. This simple synthetic method is highly attractive since the ability to prepare 3,3′- disubstituted BINOLs in advance can be useful.

A useful sulfur-transfer reaction with tetrathiomolybdate: Conversion of arylamines to aryl disulfides

A convenient method for the synthesis of a series of symmetrical aryl disulfides from arylamines via the reaction of their stable diazonium salts with tetrathiomolybdate under anhydrous conditions is described.

Resolution of (1,1'-Binaphthalene)-2,2'-dithiol by Enzyme Catalysed Hydrolysis of a Racemic Diacyl Derivative

Both enantiomers of (1,1'-binaphthalene)-2,2'-dithiol (1) can be obtained with 98percent ee by enzymatic (cholesterol esterase) resolution of the corresponding S,S'-dipentanoate.Absolute configuration and enantiomeric purity were determined by crystal structure and 1H NMR analysis, respectively, of a diastereomeric derivative of 1.

ASYMMETRIC OXIDATION OF THIOETHERS. OPTICAL RESOLUTION OF -2,2'-DITHIOL

Almost optically pure (e.e.>98percent) -2,2'-dithiol (2) is obtained by resolution of racemic 2 via the transformation of the sulfidryl functions into the corresponding thioethers 3 which are asymmetrically oxidized to diastereomeric chiral monosulfoxides 4 and then reconverted into 2.The diastereo and enantioselectivity is dependent on the structure of the thioether; i.e. the dimethylthioether 3a gives two diastereomeric sulfoxides 4a in ca. 1:1 ratio, each of them in >98percent e.e., while cyclic dithioethers 3b-d afford a single diastereomeric sulfoxide 4b-d in 46-78percent e.e..

In situ reaction monitoring reveals a diastereoselective ligand exchange reaction between the intrinsically chiral Au38(SR)24 and chiral thiols

The ligand exchange reaction between racemic Au38(2-PET) 24 (2-PET = 2-phenylethylthiolate) clusters and enantiopure 1,1′-binaphthyl-2,2′-dithiol (BINAS) was monitored in situ using a chiral high-performance liquid chromatography app

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.

A Chiral, Dendralenic C-H Acid

We report the synthesis of a chiral dendralenic C H acid, which contains three unsubstituted binaphthyl moieties. This motif and an achiral variant can be made from their corresponding bis(sulfone) precursors in one step. Despite the presence of the enantiopure binaphthyl backbone, the newly designed chiral C H acid showed only poor enantioselectivity in a Mukaiyama aldol reaction. First attempts toward the synthesis of 3,3'-hexasubstituted binaphthyl-based dendralenic acids are also reported.

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.

Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor

The invention relates to a method for preparing substituted thiophenol and heterocyclic thiophenol by a continuous flow reactor. Phenol and phenol derivatives or heterocyclic phenol are taken as starting materials, and target compounds are prepared by four-step reactions of chlorination, esterification, rearrangement and hydrolysis, wherein the rearrangement reaction is conducted in the continuousflow reactor. According to the method, the reaction is guaranteed by a miniaturized heating device for high-temperature reaction and heat generated by the reaction, the conversion rate and the yieldhigher than those in the conventional reactor are obtained in the short residence time of tens of seconds, relevant side reactions are reduced, meanwhile, fluctuation of temperature and concentrationis avoided in the reaction process, temperature run-away and overheat are avoided, and the reaction process is safe and controllable.

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.