2,2':5',2''-TERTHIOPHENE

Bezeichnung:2,2':5',2''-TERTHIOPHENE

CAS-Nr1081-34-1

Englisch Name:2,2':5',2''-TERTHIOPHENE

CBNumberCB7713541

SummenformelC12H8S3

Molgewicht248.39

MOL-Datei1081-34-1.mol

2,2':5',2''-TERTHIOPHENE physikalisch-chemischer Eigenschaften

Schmelzpunkt	93-95 °C(lit.)
Siedepunkt	160 °C (0.1 mmHg)
Dichte	1.4602 (rough estimate)
Brechungsindex	1.6200 (estimate)
Flammpunkt	160°C/0.1mm
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
Farbe	Light Yellow
Wasserlöslichkeit	Insoluble in water.
Merck	14,9174
BRN	178604
CAS Datenbank	1081-34-1(CAS DataBase Reference)
EPA chemische Informationen	.alpha.-Terthiophene (1081-34-1)

Sicherheit

R-Sätze:	36/37/38
S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	WZ9717750
F	8-10
HS Code	29349990

Gefahreninformationscode (GHS)

2,2':5',2''-TERTHIOPHENE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Chemische Eigenschaften
YELLOW TO YELLOW-BROWN POWDER
Verwenden
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.
Verwenden
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).
Definition
ChEBI: 2,2':5',2''-terthiophene is a terthiophene.
Synthesis Reference(s)
Synthetic Communications, 19, p. 307, 1989 DOI: 10.1080/00397918908050983
Synthesis, p. 462, 1991 DOI: 10.1055/s-1991-26494
Allgemeine Beschreibung
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.
Stoffwechselwegen
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.
läuterung methode
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.]

2,2':5',2''-TERTHIOPHENE Upstream-Materialien And Downstream Produkte

2,2':5',2''-TERTHIOPHENE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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