チオフェン
チオフェン · チオテトロール · チオール · チオフルフラン · チオフラン · 硫化ジビニレン · チオフェン, 2000 µg/mL in Toluene · チオフェン, 99%
識別子と物理属性
| CAS No. | 110-02-1 |
|---|---|
| 分子式 | C4H4S |
| 平均分子量 | 84.14 g/mol |
| 単同位体質量 | 84.00337113 g/mol |
| SMILES | c1ccsc1 |
| InChIKey | YTPLMLYBLZKORZ-UHFFFAOYSA-N |
| PubChem CID | 8030 |
| ChEMBL | CHEMBL278958 |
| ChEBI | CHEBI:30856 |
| EC No. | 203-729-4 |
| DTXSID | DTXSID8026145 |
| 現地名 | チオフェン |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 28.2 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 0 |
| 重原子数 | 5 |
| 形式電荷 | 0 |
| 複雑度 | 22.8 |
| 物質分類 | Other Classes -> ThiophenesFlammable agents - 3rd degree |
| SpringerMaterials Properties | Coriolis coupling |
| LogP（分配係数） | log Kow = 1.811.89 |
| 臭い | SLIGHT AROMATIC ODOR RESEMBLING BENZENEプロピレングリコール中0.10%。ネギ科ニンニク |
| 密度 | 1.0649 at 68 °F (NTP, 1992) - Denser than waterwill sink1.06494 @ 20 °C/4 °CRelative density (water = 1): 1.061.051 g/mL at 25 °C (lit.) |
| Viscosity | 0.621 mPa.s |
| Color/Form | COLORLESS LIQUID |
| 溶解度 | less than 1 mg/mL at 75 °F (NTP, 1992)MISCIBLE IN ETHANOL, ETHER, ACETONE, AND BENZENE.SOL IN ALL PROPORTIONS IN ORDINARY ORG SOLVENTS, CARBON TETRACHLORIDE, DIOXANE, PYRIMIDINE, TOLUENEwater solubility = 3,020 mg/l @ 25 °C3.01 mg/mL at 25 °CSolubility in water: none四塩化炭素、ヘプタン、ピリミジン、ジオキサン、トルエン、および多くの有機溶媒と混和性 (Keith and Walters, 1992 で引用)不溶性 |
| 引火点 | 30 °F (NTP, 1992)30 °F (-1 °C) (CLOSED CUP)-9 °C |
| 沸点 | 183.9 °F at 760 mmHg (NTP, 1992)84.0 °C @ 760 MM HG84.00 °C. @ 760.00 mm Hg84 °C84 °C (lit.) |
| Decomposition | WHEN HEATED TO DECOMPOSITION IT EMITS HIGHLY TOXIC FUMES OF SULFUR OXIDES.May be heated to 850 °C without decomposition. |
| 融点 | -36.8 °F (NTP, 1992)-39.4 °C-38.3 °C-38 °C-38 °C (lit.) |
| 蒸気密度 | 2.9 (vs air) |
| 蒸気圧 | 40 mm Hg ( 12.5 °C) |
| 屈折率 | n20/D 1.529(lit.) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 粉 |
| 色 | クリア |
| 比重 | 1.06 |
| においのタイプ | 硫黄の |
| 由来生物 | mouse |
| 臭気閾値 | 0.00056ppm |
| 爆発限界 | 1.5-12.5%(V) |
| 比熱容量 | Cp(liquid): 1.47 J/(g·K)Cp(gas): 0.87 J/(g·K), at 25℃ |
| Merck | 14,9353 |
| BRN | 103222 |
| ヘンリー定数 | 2.33 and 2.70 in distilled water and seawater, respectively (Przyjazny et al., 1983) |
| 誘電率 | 9.3(20℃) |
| 安定性 | 安定。とても燃えやすい。強力な酸化剤、硝酸塩とは相容れない。 |
| InChI | 1S/C4H4S/c1-2-4-5-3-1/h1-4H |
| InChIKey | YTPLMLYBLZKORZ-UHFFFAOYSA-N |
| SMILES | c1ccsc1 |
| LogP（分配係数） | 1.81-1.86 at pH10 |
| 表面張力 | 26.13mN/m at 298.15K |
| CAS データベース | 110-02-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Thiophene(110-02-1) |
| EPAの化学物質情報 | Thiophene (110-02-1) |
化学的特性
チオフェンは化学式C4H4Sで表される硫黄を含む芳香族化合物の一種です独特の臭いを持ち無色の液体として存在しますこの物質は石油の精製過程や石炭の加工過程で自然に生じることがあり有機化学の分野では重要な役割を果たします
化学的特性
Thiophene is a colourless to pale yellow liquid that has an odor similar to benzene. It is a heterocyclic compound with a five-membered ring containing four carbon atoms and one sulfur atom. The ring system is also known as a thienyl ring. It occurs as an impurity in commercial benzene and is used as a solvent and in organic syntheses.
化学性质
独特の臭いを有し，化合物の骨格や置換基によっては色を呈する場合がある
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 1.5% (6 of 391) of reports.DangerH225 (98.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 391 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H402: Harmful to aquatic life [Hazardous to the aquatic environment, acute hazard] |
|---|---|
| 規制情報 | Chemical: ThiopheneCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 07-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/12099Thiophene: HSNO Approval: HSR001226 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 輸送ラベル（DOT） | Flammable Liquid |
| 火災危険 | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive. |
| 火災の可能性 | A VERY DANGEROUS FIRE HAZARD WHEN EXPOSED TO HEAT OR FLAME. |
| 健康有害性 | Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:· May cause toxic effects if inhaled or absorbed through skin. |
| 有害性の概要 | Contact can cause redness of the eyes and skinInhalation can cause sore throat, cough and dizziness[ICSC] May be toxic to the liver[NJ-HSFS] A skin and eye irritantMay cause liver injury[MSDSonline] |
用途
解説
チオフェンとは、硫黄を環内に持つ五員環複素環式化合物の1つです。 チオフェンという名前は、硫黄を示す接頭語のチオ (英: thio) とを示すフェン (英: phene) を合わせて命名されています。チオール (英: thiole) と呼ばれることもありますが、チオール (英: thiol) と紛らわしいため推奨されていません。 チオフェンは、タールや石炭ガス中に少量含まれています。また、工業的には、高温環境下でブタンと硫黄を脱水素閉環反応により合成されます。
用途
ベンゼンと同様の溶剤(高温及び低温に適する)、樹脂、染料、医薬品。
使用
Thiophene is used as a building block of various organic molecules and pharmaceuticals providing functional properties.
一般的な説明
Thiophene appears as a colorless liquid with an unpleasant odor. Insoluble in water and slightly denser than water. Flash point 30 °F. Vapors heavier than air. Irritates the skin, eyes, and mucous membranes. Used to make pharmaceuticals and dyes.
使用用途
チオフェンは溶媒として用いられる他、染料・プラスチック・医農薬の原料としても利用されています。少数のチオフェンが重合したオリゴチオフェンとその機能性誘導体は、有機ELや有機電界効果トランジスタ、有機太陽電池などのハイテク用途として、幅広く使用可能です。 また、多数のチオフェンが連なった構造のポリチオフェンは、導電性高分子として使用されています。チオフェンを原料として合成される縮環チオフェンは、高性能なとして、高移動度トランジスタや有機薄膜太陽電池、有機ELなどの電子デバイスに欠かせない物資です。
製法・合成法
調製方法
Thiophene is present in coal tar and is recovered in the benzene distillation fraction (up to about 0.5% of the benzene present). Its removal from benzene is accomplished by mixing with concentrated sulfuric acid, soluble thiophene sulfonic acid being formed. Thiophene gives a characteristic blue coloration with isatin in concentrated sulfuric acid. The basic nomenclature of the thiophene ring system and its derivatives is indicated by the following: the sulfur atom is number 1, positions 2 and 5 are equivalent in the parent ring, as are the 3 and 4 positions.
純化方法
The simplest purification procedure is to dry thiophen with solid KOH, or reflux it with sodium, and fractionally distil it through a glass-helices-packed column. More extensive treatments include an initial wash with aqueous HCl, then water, drying with CaSO4 or KOH, and passage through columns of activated silica gel or alumina. Fawcett and Rasmussen [J Am Chem Soc 67 1705 1945] washed thiophene successively with 7M HCl, 4M NaOH, and distilled water, dried with CaCl2 and fractionally distilled it. *Benzene was removed by fractional crystallisation by partial freezing, and the thiophene was degassed and sealed in Pyrex flasks. [Also a method is described for recovering the thiophene from the *benzene-enriched portion.] [Beilstein 17 H 29, 17 I 17, 17 II 35, 17 III/IV 234, 17/1 V 297.]