2,2':5',2''-TERTHIOPHENE CAS NO.1081-34-1

Product Name:    2,2':5',2''-TERTHIOPHENE
Synonyms:    2,5-BIS(2-THIENYL)THIOPHENE;2,5-DI(2-THIENYL)THIOPHENE;2,2′:5′,2′′-Terthiophene,α-Terthienyl, 2,5-Di(2-thienyl)thiophene;2,2':5',2-TERTHIENYL;2,2',5',2''-TERTHIOPHENE;2,2':5',2''-Terthiophene 99%;2,2':5',2''-Terthiophene (purified by sublimation);ALPHA-TERTHIENYL
CAS:    1081-34-1
MF:    C12H8S3
MW:    248.39
EINECS:    640-441-1
Product Categories:    pharmacetical;Thiophenes;Functional Materials;Highly Purified Reagents;Other Categories;Reagents for Conducting Polymer Research;Refined Products by Sublimation;Thiophene Derivatives (for Conduting Polymer Research);Thiophene Series
Mol File:    1081-34-1.mol
 

Melting point     93-95 °C(lit.)
Boiling point     160 °C (0.1 mmHg)
density     1.4602 (rough estimate)
refractive index     1.6200 (estimate)
Fp     160°C/0.1mm
storage temp.     Keep in dark place,Sealed in dry,Room Temperature
Water Solubility     Insoluble in water.
Merck     14,9174
BRN     178604
CAS DataBase Reference    1081-34-1(CAS DataBase Reference)
EPA Substance Registry System    .alpha.-Terthiophene (1081-34-1)

Chemical Properties    YELLOW TO YELLOW-BROWN POWDER
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).
Synthesis Reference(s)    Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983
Synthesis, p. 462, 1991 DOI: 10.1055/s-1991-26494
Metabolic pathway    When 14C-a-terthienyl is administered orally to rats in a single dose, two metabolites [1,4-di(2'-thienyl)]-1,4- butadione and 2-2' -bithiophene-5-carboxylic acid are identified in the urine.
Purification Methods    Possible impurities are bithienyl and polythienyls. Suspend it in H2O and steam distil it to remove bithienyl. The residue is cooled and extracted with CHCl3, dried (MgSO4), filtered, evaporated and the residue chromatographed on Al2O3 using pet ether/3% Me2CO as eluent. The terphenyl zone is then eluted from the Al2O3 with Et2O, the extract is evaporated and the residue is recrystallised from MeOH (40mL per g). The platelets are washed with cold MeOH and dried in air. [UV: Sease & Zechmeister J Am Chem Soc 69 270 1947; Uhlenbroek & Bijloo Recl Trav Chim Pays-Bas 79 1181 1960.] It has also been recrystallised from MeOH, *C6H6, pet ether or AcOH. [UV: Zechmeister & Sease J Am Chem Soc 69 273 1947, Steinkopf et al. Justus Liebigs Ann Chem 546 180 1941.] It is a phototoxic nematocide [Cooper & Nitsche Bioorg Chem 13 36 1985, Chan et al. Phytochem 14 2295 1975]. [Beilstein 19 III/IV 4763, 19/9 V 226.]