5-(Thien-2-yl)thiophene-2-carbonitrile

Base Information

• Chemical Name: 5-(Thien-2-yl)thiophene-2-carbonitrile
• CAS No.: 16278-99-2
• Molecular Formula: C₉H₅NS₂
• Molecular Weight: 191.277
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90372344
• Nikkaji Number: J730.337H
• Wikidata: Q82160009
• Mol file: 16278-99-2.mol

Synonyms:16278-99-2;5-(thien-2-yl)thiophene-2-carbonitrile;[2,2'-Bithiophene]-5-carbonitrile;2,2'-bithiophene-5-carbonitrile;5-thiophen-2-ylthiophene-2-carbonitrile;5-(thiophen-2-yl)thiophene-2-carbonitrile;Maybridge3_006613;5-Cyano-2,2'-bithiophene;SCHEMBL498548;DTXSID90372344;HMS1449M13;CCG-43423;MFCD01812635;AKOS004120186;IDI1_018000;MS-22114;FT-0619743;SR-01000633345-1

Chemical Property of 5-(Thien-2-yl)thiophene-2-carbonitrile

Chemical Property:

• Vapor Pressure: 0.00029mmHg at 25°C
• Melting Point: 100 °C
• Refractive Index: 1.667
• Boiling Point: 36 °C
• Flash Point: 148.5°C
• PSA: 80.27000
• Density: 1.36g/cm³
• LogP: 3.34828
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 190.98634151
• Heavy Atom Count: 12
• Complexity: 208

Purity/Quality:

98%min ^*data from raw suppliers

5-(Thien-2-yl)thiophene-2-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: S36/37:Wear suitable protective clothing and gloves.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC=C(S2)C#N
• Description: 2,2'-bithiophene-5-carbonitrile is the intermediate used for the synthesis of 3,6-bis[5-(2,2'-bithiophene)]pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione which can be further modified?to form oligomers or polymers used for organic electronic devices.

Technology Process of 5-(Thien-2-yl)thiophene-2-carbonitrile

There total 8 articles about 5-(Thien-2-yl)thiophene-2-carbonitrile 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: 94.0%

2,2'-bithiophene-5-carboxaldehyde (3779-27-9) → 2,2’-bithiophene-5-carbonitrile (16278-99-2)

Guidance literature:

With ammonium hydroxide; iodine; In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1039/c4tc01008f

Reference yield:

5-bromo-2-thiophencarboxaldehyde (4701-17-1) → 2,2’-bithiophene-5-carbonitrile (16278-99-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Pd(PPh₃)4 / dioxane / 24 h / 80 - 90 °C

2: aq. NH₂OH*HCl; Na₂CO₃ / methanol / 6 h / Heating

3: Ac₂O / 4 h / Heating

With hydroxylamine hydrochloride; acetic anhydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; methanol; 1: Stille coupling;

Reference yield:

2,2'-Bithiophene (492-97-7) → 2,2’-bithiophene-5-carbonitrile (16278-99-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide

2: dimethyl sulfoxide

With N-Bromosuccinimide; In dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/c0cp01553a

upstream raw materials:

5,5'-dibromo-2,2'-bisthiophene

1-cyanobenzotriazole

2,2'-Bithiophene

2,2'-bithiophene-5-carbaldoxime

Downstream raw materials:

5-bromo-2,2’-bithiophene-5’-carbonitrile

Refernces

• 1、 Prabhu, Deepak D.,Sivadas, Aneesh P.,Das, Suresh. "Solvent assisted fluorescence modulation of a C3-symmetric organogelator". supporting information. p. 7039 - 7046. Retrieved 2014/08/18.
• 2、 Ismail, Mohamed A.. "An efficient synthesis of 5′-(4-cyanophenyl)-2,2′-bifuran-5- carbonitrile and analogues". . p. 733 - 737. Retrieved 2007/10/03.