2,2':5',2''-Terthiophene
α-Terthiophene · terthienyl · TERTHIOPHENE · 3TH · TTh · S1130 · 2,2':5' · 2,2':5',2
Identifiers & Physical Properties
| CAS No. | 1081-34-1 |
|---|---|
| Molecular formula | C12H8S3 |
| Average molar mass | 248.4 g/mol |
| Monoisotopic mass | 247.97881326 g/mol |
| SMILES | c1csc(-c2ccc(-c3cccs3)s2)c1 |
| InChIKey | KXSFECAJUBPPFE-UHFFFAOYSA-N |
| PubChem CID | 65067 |
| ChEMBL | CHEMBL90017 |
| ChEBI | CHEBI:10335 |
| EC No. | 640-441-1 |
| DTXSID | DTXSID2041206 |
Chemical & Physical Properties
| XLogP | 4.4 |
|---|---|
| Topological polar surface area | 84.7 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 2 |
| Heavy atoms | 15 |
| Formal charge | 0 |
| Complexity | 197 |
| SpringerMaterials Properties | Angular frequency |
| Collision Cross Section | 146.4 Ų [M]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2041206] |
| Melting point | 93-95 °C(lit.) |
| Boiling point | 160 °C (0.1 mmHg) |
| Density | 1.4602 (rough estimate) |
| Refractive index | 1.6200 (estimate) |
| Flash point | 160°C/0.1mm |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | Chloroform (Slightly), Methanol (Slightly)Insoluble in water. |
| Physical state | Solid |
| Color | Light Yellow |
| Merck | 14,9174 |
| BRN | 178604 |
| InChI | InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H |
| InChIKey | KXSFECAJUBPPFE-UHFFFAOYSA-N |
| SMILES | C1(C2SC(C3SC=CC=3)=CC=2)SC=CC=1 |
| CAS DataBase Reference | 1081-34-1(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 0P77RAU2RR |
| EPA Substance Registry System | .alpha.-Terthiophene (1081-34-1) |
| UNSPSC Code | 12352103 |
| NACRES | NA.23 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 3 |
| RTECS number | WZ9717750 |
| F | 8-10 |
| Customs code | 29349990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.WarningH315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (25%) |
| F | 8-10 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| RTECS number | WZ9717750 |
| Customs code | 29349990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 22-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
Applications & Uses
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).
Uses
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.
General Description
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.