2,2':5',2''-Terthiophene

Base Information

• Chemical Name: 2,2':5',2''-Terthiophene
• CAS No.: 1081-34-1
• Molecular Formula: C12H8S3
• Molecular Weight: 248.394
• Hs Code.: 29349990
• European Community (EC) Number: 640-441-1
• UNII: 0P77RAU2RR
• DSSTox Substance ID: DTXSID2041206
• Nikkaji Number: J102.960F
• Wikipedia: Terthiophene
• Wikidata: Q3491255
• Metabolomics Workbench ID: 53529
• ChEMBL ID: CHEMBL90017
• Mol file: 1081-34-1.mol

Synonyms:2,2,5,2''-terthiophene;alpha-terthienyl;alpha-terthiophene;terthiophene

Chemical Property of 2,2':5',2''-Terthiophene

Chemical Property:

• Appearance/Colour: Yellow to yellow-brown powder
• Melting Point: 93-95 °C(lit.)
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 361.3 °C at 760 mmHg
• Flash Point: 128.4 °C
• PSA: 84.72000
• Density: 1.318 g/cm³
• LogP: 5.20510
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 247.97881378
• Heavy Atom Count: 15
• Complexity: 197

Purity/Quality:

99% ^*data from raw suppliers

2,2'':5'',2''''-Terthiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC=C(S2)C3=CC=CS3
• Uses: α-Terthienyl was first recognized as a nematicidal constituent of marigolds, but in the presence of light, it is also highly toxic to larvae of several insect species, including mosquitoes. This electron donor thiophenederivative phototoxin is biosynthesized from polyacetylene precursors and appears to function as a photosensitizer catalyzing the formation of reactive oxygen species at the target site (25). 2,2'':5'',2''''-Terthiophene is a thiophene compound isolated from the roots of Echinops transiliensis, and was studied for its larvicidal activity against Aedes aegypti. 2,2'':5'',2''''-Terthiophene also showed inhibitory effects on dispersal ability of Bursaphelenchus xylophilus when used synergistically with certain antibiotics.

Technology Process of 2,2':5',2''-Terthiophene

There total 58 articles about 2,2':5',2''-Terthiophene 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: 97.5%

2-bromothiophene (1003-09-4) + 2,5-dibromothiophen (3141-27-3) → 2,2':5',2''-terthiophene (1081-34-1)

Guidance literature:

2-bromothiophene; With magnesium; In tetrahydrofuran; for 5h; Reflux; Large scale;

2,5-dibromothiophen; With Ni(1,2-bis(diphenylphosphanyl)-benzene)Cl₂; In tetrahydrofuran; at 19.84 - 64.84 ℃; for 1.75h; Reagent/catalyst; Solvent; Temperature; Concentration; Time; Thermodynamic data; Inert atmosphere; Large scale;

DOI:10.1021/op020044n

Reference yield: 97.0%

2,5-dibromothiophen (3141-27-3) + thiophen-2-yl magnesium bromide (5713-61-1) → 2,2':5',2''-terthiophene (1081-34-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; at 0 - 35 ℃; for 13.5h;

Reference yield: 93.0%

1,4-bis(2-thienyl)butadiyne (16900-51-9) → 2,2':5',2''-terthiophene (1081-34-1)

Guidance literature:

With sodiumsulfide nonahydrate; dimethyl sulfoxide; potassium hydroxide; at 80 ℃; for 4h;

DOI:10.1016/j.tet.2014.09.025

upstream raw materials:

2-Iodothiophene

thiophene

2-thienyl chloride

2-bromothiophene

Downstream raw materials:

5,5'-dibromo-2,2':5'2''-terthiophene

tetracyanoethylene radical cation

methyl viologen cation radical

2,2':5',2''-terthiophene-5-carboxaldehyde

Refernces

• 1、 Liu, Ping,Liu, Miaomiao,Deng, Wenji. "Synthesis and mesogenic properties of novel terthiophene derivatives". . p. 685 - 692. Retrieved 2006.
• 2、 Wang, Dong-Liang,Hwang, Wen-Shu. "Oligomerization of thiophene in the presence of PdCl42-". . p. C29 - C32. Retrieved 1991.
• 3、 Yin, Pengcheng,Niu, Qingfen,Yang, Qingxin,Lan, Linxin,Li, Tianduo. "A new “naked-eye” colorimetric and ratiometric fluorescent sensor for imaging Hg2+ in living cells". . . Retrieved 2019.
• 4、 Beny, Jean-Pierre,Dhawan, Som N.,Kagan, Jacques,Sundlass, Satinder. "Synthesis of 3,2':5',3''-Terthiophene and Other Terthiophenes by the Thiophenecarboxaldehyde Ethynylthiophene Dithienylbutadiyne Route". . p. 2201 - 2204. Retrieved 1982.
• 5、 Wang, Jing,Liu, Ke,Liu, Yi-Yang,Song, Cheng-Li,Shi, Zi-Fa,Peng, Jun-Biao,Zhang, Hao-Li,Cao, Xiao-Ping. "New oligothiophene-pentacene hybrids as highly stable and soluble organic semiconductors". . p. 2563 - 2566. Retrieved 2009.
• 6、 Sears, Wendy A.,MacKinnon, Craig D.,Mawhinney, Robert C.,Sinnemaki, Lauren C.,Johnson, Matthew J.,Winter, A. John,Robertson, Craig M.. "Using the nitro group to induce p-stacking in terthiophenes". . p. 309 - 317. Retrieved 2010.
• 7、 Marshall, Nicholas,James, William,Fulmer, Jeremy,Crittenden, Scott,Thompson, Anthony B.,Ward, Patrick A.,Rowe, Gerard T.. "Polythiophene Doping of the Cu-Based Metal-Organic Framework (MOF) HKUST-1 Using Innate MOF-Initiated Oxidative Polymerization". . p. 5561 - 5575. Retrieved 2019.
• 8、 Byron,Matharu,Wilson,Wright. "Synthesis and liquid crystal properties of certain 5,5″-disubstituted 2,2′:5′,2″-terthienyls". . p. 227 - 230. Retrieved 1995.
• 9、 Alberst, Willem M.,Canters, Gerard W.,Reedijk, Jan. "Preparation of extended di(4-pyridyl)thiophene oligomers". . p. 3895 - 3904. Retrieved 1995.
• 10、 Melucci, Manuela,Barbarella, Giovanna,Sotgiu, Giovanna. "Solvent-free, microwave-assisted synthesis of thiophene oligomers via suzuki coupling". . p. 8877 - 8884. Retrieved 2002.