CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE

Base Information

• Chemical Name: CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE
• CAS No.: 112440-46-7
• Molecular Formula: C₁₈H₁₈N₂S₂
• Molecular Weight: 326.486
• Hs Code.: 2934999090
• Mol file: 112440-46-7.mol

Synonyms:2-Butenedinitrile,2,3-bis(2,4,5-trimethyl-3-thienyl)-, (Z)-; (Z)-1,2-Dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene;(Z)-2,3-Bis(2,4,5-trimethyl-3-thienyl)-2-butenedinitrile; B 1536; CMTE(O-form); CMTE open form;cis-1,2-Dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene

Chemical Property of CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE

Chemical Property:

• Melting Point: 121 °C
• Refractive Index: 1.611
• Boiling Point: 441.5±45.0 °C(Predicted)
• PSA: 104.06000
• Density: 1.183±0.06 g/cm3(Predicted)
• LogP: 5.61796
• Solubility.: slightly sol. in Methanol

Purity/Quality:

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

cis-1,2-Dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE

There total 11 articles about CIS-1,2-DICYANO-1,2-BIS(2,4,5-TRIMETHYL-3-THIENYL)ETHENE 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:

3-(cyanomethyl)-2,4,5-trimethylthiophene (112440-49-0) → 1,2-dicyano-1,2-bis(2,3,5-trimethyl-3-thienyl)ethene (112440-46-7) + (E)-2,3-Bis-(2,5-dimethyl-thiophen-3-yl)-but-2-enedinitrile

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In tetrachloromethane; at 45 ℃; for 1.5h; Yield given;

DOI:10.1021/jo00239a022

Reference yield:

2,4,5-trimethylthiophene (1795-05-7) → 1,2-dicyano-1,2-bis(2,3,5-trimethyl-3-thienyl)ethene (112440-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / SnCl₄ / CS₂ / 1 h / 0 °C

2: 85 percent / triethylbenzylammonium chloride / H₂O / 1 h / Heating

3: 50percent aq. NaOH, triethylbenzylamonium chloride / CCl₄ / 1.5 h / 45 °C

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; tin(IV) chloride; In carbon disulfide; tetrachloromethane; water;

DOI:10.1021/jo00239a022

Reference yield:

2,3,5-trimethyl-4-(chloromethyl)thiophene (63826-43-7) → 1,2-dicyano-1,2-bis(2,3,5-trimethyl-3-thienyl)ethene (112440-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / triethylbenzylammonium chloride / H₂O / 1 h / Heating

2: 50percent aq. NaOH, triethylbenzylamonium chloride / CCl₄ / 1.5 h / 45 °C

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In tetrachloromethane; water;

DOI:10.1021/jo00239a022

upstream raw materials:

3-(cyanomethyl)-2,4,5-trimethylthiophene

2,4,5-trimethylthiophene

2,3,5-trimethyl-4-(chloromethyl)thiophene

trans-1,2-dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene

Downstream raw materials:

trans-1,2-dicyano-1,2-bis(2,4,5-trimethyl-3-thienyl)ethene

1,2-bis(2,4,5-trimethylthiophene-3-yl)maleic anhydride

Refernces

• 1、 Ishitobi, Hidekazu,Sekkat, Zouheir,Kawata, Satoshi. "Individualized optically induced orientation of photochemical isomers". . p. 421 - 428. Retrieved 1999.
• 2、 Murase, Seiichiro,Teramoto, Madoka,Furukawa, Hidemitsu,Miyashita, Yoshiharu,Horie, Kazuyuki. "Photochemically induced fluorescence control with intermolecular energy transfer from a fluorescent dye to a photochromic diarylethene in a polymer film". . p. 964 - 966. Retrieved 2003.
• 3、 Inoue, Takeshi,Inokuchi, Makoto. "Shear stress- and visible light-induced photochromism on diarylethene". . p. 911 - 913. Retrieved 2015.
• 4、 Patra, Abhijit,Metivier, Remi,Brisset, Francois,Nakatani, Keitaro. "Photochromic one-dimensional nanostructures based on dithienylethene: Fabrication by light-induced precipitation and reversible transformation in the nanoparticle state". supporting information; experimental part. p. 2489 - 2491. Retrieved 2012/04/04.