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Terthiophene

Chemical compound From Wikipedia, the free encyclopedia

Terthiophene is the organic compound with the formula [C4H3S]2C4H2S. It is an oligomer of the heterocycle thiophene, a shorter oligomer is dithienyl, and the parent polymer is polythiophene. In the most common isomer of terthiophene, two thienyl groups are connected via their 2 positions to a central thiophene, also at the carbon atoms flanking the sulfur.

Quick facts Names, Identifiers ...
Terthiophene
Terthiophene
Terthiophene
Names
Preferred IUPAC name
12,22:25,32-Terthiophene
Other names
α-Terthienyl
2,5-Di(2-thienyl)thiophene
Identifiers
3D model (JSmol)
178604
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.168.218 Edit this at Wikidata
EC Number
  • 640-441-1
KEGG
RTECS number
  • WZ9717750
UNII
  • InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H checkY
    Key: KXSFECAJUBPPFE-UHFFFAOYSA-N checkY
  • InChI=1/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
    Key: KXSFECAJUBPPFE-UHFFFAOYAI
  • s1cccc1c2sc(cc2)c3sccc3
Properties
C12H8S3
Molar mass 248.39 g/mol
Appearance pale yellow solid
Melting point 93-95 °C
insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 flammable
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds
 Thiophene
polythiophene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation of terthiophene

Terthiophene is prepared by the nickel- or palladium-catalysed coupling reaction of 2,5-dibromothiophene with the Grignard reagent derived from 2-bromothiophene.[2]

Properties and applications

This substance is likely responsible for the insecticidal activity of Tagetes minuta as it can react with light and oxygen to make singlet oxygen.[3][4]

Together with derivatives of 2,2'-bithiophene, various chlorinated terthiophenes occur naturally in thistles.[5]

Terthiophene has been employed as building block for the organic semi-conductor polythiophene.

See also

References

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