(+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL

Base Information

• Chemical Name: (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL
• CAS No.: 102555-71-5
• Molecular Formula: C₂₀H₁₄S₂
• Molecular Weight: 318.463
• Mol file: 102555-71-5.mol

Synonyms:(+/-)-1.1'-Binaphthalene-2,2'-dithiol;1-(2-Sulfanylnaphthalen-1-yl)naphthalene-2-thiol;

Chemical Property of (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL

Chemical Property:

• Boiling Point: 495 °C at 760 mmHg
• Flash Point: 230.1 °C
• PSA: 77.60000
• Density: 1.283 g/cm³
• LogP: 6.23740

Purity/Quality:

99% ^*data from raw suppliers

(+/-)-1,1'-BINAPHTHALENE-2,2'-DITHIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,1''-Binaphthyl-2,2''-dithiol is used in the preparation of chiral, atropisomeric organosulfur compounds.

Technology Process of (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL

There total 39 articles about (+/-)-1.1'-BINAPHTHALENE-2,2'-DITHIOL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(R)-(-)-dinaphtho<2,1-c:1',2'-e><1,2>dithiin (188-57-8,79252-43-0,79252-44-1) → 1,1'-binaphthalene-2,2'-dithiol (102555-71-5,124414-36-4,124414-37-5)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;

DOI:10.1016/0957-4166(94)00387-Q

Reference yield: 95.0%

(R)-(1,1'-binaphthalene-2,2'-diyl) S,S'-bis(N,N'-dimethylthiocarbamate) → (R)-1,1′-binaphthalene-2,2′-dithiol (55441-99-1,102555-71-5,124414-36-4,124414-37-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 50 ℃; for 12h;

DOI:10.1021/ja806875c

Reference yield: 92.0%

<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate) (147923-23-7,189084-89-7,155727-93-8) → 1,1'-binaphthalene-2,2'-dithiol (102555-71-5,124414-36-4,124414-37-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; methanol; for 5h; Heating;

upstream raw materials:

<1,1'-Binaphthalene>-2,2'-diyl S,S-bis(N,N-dimethylthiocarbamate)

C₂₉H₂₄O₅S₂

(R)-(-)-dinaphtho<2,1-c:1',2'-e><1,2>dithiin

pentanethioic acid S,S'-<(1,1'-binaphthalene)-2,2'-diyl> ester

Downstream raw materials:

(+)-<1,1'-binaphthalene>-2,2'-dithiol

(-)-<1,1'-binaphthalene>-2,2'-dithiol

(Ra)-1,1'-binaphthyl-2,2'-disulfonic acid

Pt(Ph₂P(CH₂)3PPh₂)(1,1'-dinaphthalene-2,2'-dithiolate)

Refernces

• 1、 Fabbri, Davide,Delogu, Giovanna,Lucchi, Ottorino De. "A Widely Applicable Method of Resolution of Binaphthyls: Preparation of Enantiomerically Pure 1,1'-Binaphthalene-2,2'-diol, 1,1'-Binaphthalene-2,2'-dithiol, 2'-Mercapto-1,1'-binaphthalen-2-ol, and 1,1'-binaphthalene-8,8'-diol". . p. 6599 - 6601. Retrieved 1995.
• 2、 Kiefer, Matthias,Vogel, Rainer,Helmchen, Guenter,Nuber, Bernhard. "Resolution of (1,1'-Binaphthalene)-2,2'-dithiol by Enzyme Catalysed Hydrolysis of a Racemic Diacyl Derivative". . p. 7109 - 7114. Retrieved 1994.
• 3、 Knoppe, Stefan,Azoulay, Raymond,Dass, Amala,Bürgi, Thomas. "In situ reaction monitoring reveals a diastereoselective ligand exchange reaction between the intrinsically chiral Au38(SR)24 and chiral thiols". . p. 20302 - 20305. Retrieved 2012.
• 4、 H?fler, Denis,List, Benjamin. "A Chiral, Dendralenic C-H Acid". supporting information. p. 38 - 39. Retrieved 2021/12/29.
• 5、 -. "Method for preparing substituted thiophenol and heterocyclic thiophenol by continuous flow reactor". Paragraph 0093-0094; 0097-0098. . Retrieved 2019/01/14.