2,2':5',2"-ターチオフェン
2,2':5',2"-ターチオフェン · α-テルチエニル · 2,5':2',2''-テルチオフェン · 2,2':5',5''-テルチオフェン · α-テルチオフェン · 2,5':2',5''-テルチオフェン · 2,5-ジ(2-チエニル)チオフェン · 2,2':5',2''-テル(チオフェン)
識別子と物理属性
| CAS No. | 1081-34-1 |
|---|---|
| 分子式 | C12H8S3 |
| 平均分子量 | 248.4 g/mol |
| 単同位体質量 | 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 |
| 現地名 | 2,2':5',2"-ターチオフェン |
化学・物理的性質
| XLogP | 4.4 |
|---|---|
| 極性表面積 | 84.7 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 15 |
| 形式電荷 | 0 |
| 複雑度 | 197 |
| SpringerMaterials Properties | Angular frequency |
| Collision Cross Section | 146.4 Ų [M]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2041206] |
| 融点 | 93-95 °C(lit.) |
| 沸点 | 160 °C (0.1 mmHg) |
| 密度 | 1.4602 (rough estimate) |
| 屈折率 | 1.6200 (estimate) |
| 引火点 | 160°C/0.1mm |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | クロロホルム（微量）、メタノール（微量）水に不溶。 |
| 外観・状態 | 個体 |
| 色 | ライトイエロー |
| 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 データベース | 1081-34-1(CAS DataBase Reference) |
| EPAの化学物質情報 | .alpha.-Terthiophene (1081-34-1) |
化学的特性
YELLOW TO YELLOW-BROWN POWDER
安全性と法規制
| GHS 分類 | 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 |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | WZ9717750 |
| 税関コード | 29349990 |
| 危険文句（R） | 36/37/38 |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
用途
有機合成原料。
使用
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).
一般的な説明
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.
製法・合成法
純化方法
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.]