2,2′:5′,2′′-Terthiophene - ≥99% , CAS No.1081-34-1

CAS: 1081-34-1 Cat. No.: T103177 Molecular Weight: 248.39 Beilstein Registry Number: 178604 EC Number: 640-441-1 PubChem CID: 65067

GRADE & PURITY ≥99%

Synonyms

2,2':5',2''-Terthiophene | 2,2':5',2'-Terthiophene | 2,2:5,2-Terthiophene | 2,5-dithiophen-2-ylthiophen | InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8 | AC-4934 | W-200083 | MFCD00012167 | T1196 | 2,2':5'2''-Terthiophene | AKOS0052576

Storage

Protected from light,Room temperature

Shipped In

Normal

Overview

Product Describtion:

2,2′:5′,2′′-Terthiophene (3T) is a tri-thiophene based low band conductive polymer that is prepared by reacting 2,5-dibromothiophene and thienylmagnesium bromide in the presence of nickel catalyst.
2,2′:5′,2′′-Terthiophene (TTh) may be prepared by nickel catalysed coupling reaction of grignard′s reagent derived from 2-bromothiophene and magnesium. It generates singlet oxygen. In nature, it is found in the floral extract of Tagetes minuta and Echinops grijisii.It is known to be toxic to mosquitoes.It also exihibits antifungal activity.

Product Application:

3T can be combined with 3,4-ethylenedioxythiophene (EDOT) in a tetrabutylammonium perchlorate solution for use as an electrochromic copolymer for a wide range of applications like photovoltaics and polymer light emitting diodes (LEDs).It can also be used to form metal-organic based thin films with metals like aluminum, silver, and calcium which can potentially be used for optoelectronics based applications.
Electrochemical copolymerization of carbazole and TTh in sodium perchlorate/acetonitrile was reported. Electrochromic copolymer based on TTh and 3, 4-ethylenedioxythiophene has been reported. TTh acts as a monomer precursor for polythiophene and as a dopant for polycarbonate. It may function as a photosensitizer.

Specifications

Synonyms

2, 2':5', 2''-Terthiophene | 2, 2':5', 2'-Terthiophene | 2, 2:5, 2-Terthiophene | 2, 5-dithiophen-2-ylthiophen | InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8 | AC-4934 | W-200083 | MFCD00012167 | T1196 | 2, 2':5'2''-Terthiophene | AKOS0052576

Specifications & Purity

≥99%

Storage

Protected from light, Room temperature

Shipped In

Normal

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Pubchem Sid: 488183656
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488183656
• Canonical Smiles: C1=CSC(=C1)C2=CC=C(S2)C3=CC=CS3
• IUPAC Name: 2,5-dithiophen-2-ylthiophene
• InChIKey: KXSFECAJUBPPFE-UHFFFAOYSA-N
• INCHI: 1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
• Isomeric SMILES: C1=CSC(=C1)C2=CC=C(S2)C3=CC=CS3
• WGK Germany: 3
• RTECS: WZ9717750
• PubChem CID: 65067
• Molecular Weight: 248.39
• Beilstein: 178604
• Reaxy-Rn: 178604

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Bi- and oligothiophenes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Bi- and oligothiophenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Bi- and oligothiophenes
• Alternative Parents: 2,5-disubstituted thiophenes Heteroaromatic compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Bithiophene - 2,5-disubstituted thiophene - Heteroaromatic compound - Thiophene - Hydrocarbon derivative - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.
• External Descriptors: terthiophene

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Plasmopara viticola (181 Activities)

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Fusarium oxysporum (3998 Activities)

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Botrytis cinerea (4183 Activities)

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Colletotrichum fragariae (147 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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Aedes atropalpus (23 Activities)

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Heterodera zeae (651 Activities)

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Colletotrichum acutatum (300 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Insoluble in water, soluble in acetone, benzene, ether, slightly soluble in ethanol, methanol
• Sensitivity: Insoluble in water, soluble in acetone, benzene, ether, slightly soluble in ethanol, methanol
• Melt Point(°C): 93-95°C
• Molecular Weight: 248.400 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 247.979 Da
• Monoisotopic Mass: 247.979 Da
• Topological Polar Surface Area: 84.700 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 197.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xinsheng Tang, Hujun Zhang, Ruxangul Jamal, Abdukeyum Abdurexit, Nawrzhan Serkjan, Shuyue Xie, Yiming Liu, Tursun Abdiryim.  (2023)  High performance self-powered ultraviolet photodetectors based on P(TTh-co-EDOT) copolymer sensitized TiO2 NRs.  Surfaces and Interfaces,      [PMID:] [10.1016/j.surfin.2023.103802]

2. Xuehui Pang, Rui Liu, Xiaoyi Lv, Wenjun Lu, Lebin Sun, Qiuyan Wang, Zhen Li, Qing Kang, Jiandong Xie, Yingxin Pang, Feimeng Zhou.  (2024)  Functionalizable poly-terthiophene/Cu2O heterojunction constructed in situ for sensitive photoelectrochemical detection of long non-coding RNA markers.  RSC Advances,  14  (45): (32883-32892).  [PMID:39429932] [10.1039/D4RA05238B]

3. Rusen Zou, Babak Rezaei, Xiaoyong Yang, Wenjing Zhang, Stephan Sylvest Keller, Yifeng Zhang.  (2024)  Novel bio-solar hybrid photoelectrochemical synthesis for selective hydrogen peroxide production.  GREEN CHEMISTRY,  26  (14): (8367-8382).  [PMID:] [10.1039/D4GC02220C]

4. Yaqiong Qiu, Qichao Liu, Mingzhu Qiu, Yafang Shang, Shangrong Zhu, Fengru Liu, Shike She, Shaohua Yang, Xiangli Niu.  (2025)  Ultrasonic-assisted extraction and light-dependent antimicrobial activities of thiophenes from Tagetes erecta.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2025.122099]