1,2-Bis(2-cyanoethylthio)ethane

Base Information

• Chemical Name: 1,2-Bis(2-cyanoethylthio)ethane
• CAS No.: 86180-54-3
• Molecular Formula: C₈H₁₂N₂S₂
• Molecular Weight: 200.329
• Hs Code.: 2930909090
• European Community (EC) Number: 680-044-0
• NSC Number: 215744
• DSSTox Substance ID: DTXSID00235436
• Nikkaji Number: J2.222.288K
• Wikidata: Q72444773
• Mol file: 86180-54-3.mol

Synonyms:1,2-Bis(2-cyanoethylthio)ethane;86180-54-3;3,3'-(Ethylenedithio)dipropionitrile;3-[2-(2-cyanoethylsulfanyl)ethylsulfanyl]propanenitrile;Propanenitrile, 3,3'-(1,2-ethanediylbis(thio))bis-;propanenitrile, 3,3'-[1,2-ethanediylbis(thio)]bis-;3,3'-(ethane-1,2-diylbis(sulfanediyl))dipropanenitrile;BRN 1760850;Propionitrile, 3,3'-(ethylenedithio)di-;Propionitrile, beta,beta'-(ethylenedithio)di-;3,3'-(1,2-Ethanediylbis(thio))bispropanenitrile;3,3-(Ethylenedithio)dipropionitrile;NSC215744;4,7-Dithiadecanedinitrile;3-03-00-00558 (Beilstein Handbook Reference);SCHEMBL2991686;DTXSID00235436;1,2-Bis(2-cyanoethyl thio)ethane;MFCD00475273;AKOS015836387;NSC 215744;NSC-215744;CS-0365793;E0673;FT-0693880;T73007

Chemical Property of 1,2-Bis(2-cyanoethylthio)ethane

Chemical Property:

• Vapor Pressure: 2.09E-07mmHg at 25°C
• Melting Point: 93 °C
• Refractive Index: 1.539
• Boiling Point: 424.3 °C at 760 mmHg
• Flash Point: 210.4 °C
• PSA: 98.18000
• Density: 1.142 g/cm³
• LogP: 2.28016
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 200.04419074
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,3''-(Ethylenedithio)dipropionitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CSCCSCCC#N)C#N
• Uses: 3,3''-(Ethylenedithio)dipropionitrile is a useful compound in organic synthesis.

Technology Process of 1,2-Bis(2-cyanoethylthio)ethane

There total 4 articles about 1,2-Bis(2-cyanoethylthio)ethane 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: 98.0%

ethane-1,2-dithiol (540-63-6) + acrylonitrile (107-13-1,25014-41-9) → 3,3′-(ethane-1,2-diylbis(sulfanediyl))dipropanenitrile (86180-54-3)

Guidance literature:

With potassium carbonate; at 53 ℃; for 0.5h; Sonication;

DOI:10.1021/acs.joc.9b01682

Reference yield: 88.0%

bromopropionitrile (2417-90-5) + ethane-1,2-dithiol (540-63-6) → 3,3′-(ethane-1,2-diylbis(sulfanediyl))dipropanenitrile (86180-54-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jm990211i

Reference yield:

bis (2-chloroethyl) sulphide (505-60-2) + potassium cyanide (151-50-8) → 3,3′-(ethane-1,2-diylbis(sulfanediyl))dipropanenitrile (86180-54-3)

Guidance literature:

With ethanol;

upstream raw materials:

ethanol

bis (2-chloroethyl) sulphide

potassium cyanide

ethane-1,2-dithiol

Downstream raw materials:

11,11'-[1,4-phenylenebis(methylene)]bis[8-(p-toluenesulfonyl)-1,4-dithia-8,11-diazacyclotetradecane]

8,11-bis(p-toluenesulfonyl)-1,4-dithia-8,11-diazacyclotetradecane

1,12-bis(p-toluenesulfonyl)-5,8-dithia-1,12-diazadodecane

8-(p-toluenesulfonyl)-1,4-dithia-8,11-diazacyclotetradecane

Refernces

• 1、 Chahdoura, Faouzi,Pradel, Christian,Gomez, Montserrat. "Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes". supporting information. p. 3648 - 3660. Retrieved 2014/01/06.
• 2、 Zhang, Huaxing,Zhang, Yuhong,Liu, Leifang,Xu, Hailiang,Wang, Yanguang. "RuCl3 in poly(ethylene glycol): A highly efficient and recyclable catalyst for the conjugate addition of nitrogen and sulfur nucleophiles". . p. 2129 - 2136. Retrieved 2007/10/03.