1,1'-チオカルボニルジイミダゾール
1,1'-チオカルボニルジイミダゾール · 1,1'-(チオキソメチレン)ビス(1H-イミダゾール) · ジ(1H-イミダゾール-1-イル)チオケトン · ビス(1H-イミダゾール-1-イル)チオケトン · ビス(1-イミダゾリル)チオケトン · 1,1'-(チオカルボニル)ビス(1H-イミダゾール) · 1,1'-カルボノチオイルビス(1H-イミダゾール) · 1,1’-（チオカルボニル）ビス（1Hイミダゾル）
識別子と物理属性
| CAS No. | 6160-65-2 |
|---|---|
| 分子式 | C7H6N4S |
| 平均分子量 | 178.22 g/mol |
| 単同位体質量 | 178.03131719 g/mol |
| SMILES | S=C(n1ccnc1)n1ccnc1 |
| InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N |
| PubChem CID | 80264 |
| EC No. | 228-183-4 |
| DTXSID | DTXSID70210614 |
| 現地名 | 1,1'-チオカルボニルジイミダゾール |
化学・物理的性質
| XLogP | 0.7 |
|---|---|
| 極性表面積 | 67.7 |
| 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 | 0 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 166 |
| 物質分類 | Nitrogen Compounds -> Imidazoles |
| Physical Description | Yellow powder[Alfa Aesar MSDS] |
| 融点 | 98-102 °C(lit.) |
| 沸点 | 342°C (rough estimate) |
| 密度 | 1.3046 (rough estimate) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | 2-8°C |
| 溶解度 | テラヒドロフラン、トルエン、ジクロロメタンに可溶。分解する |
| pKa（酸解離定数） | 1.96±0.10(Predicted) |
| 外観・状態 | 粉 |
| 色 | 明るい黄色 |
| BRN | 609349 |
| 安定性 | 安定していますが、空気や湿気に敏感です。強酸化剤、強酸とは相容れない。 |
| InChI | 1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H |
| InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N |
| SMILES | S=C(n1ccnc1)n2ccnc2 |
| CAS データベース | 6160-65-2(CAS DataBase Reference) |
化学的特性
yellow powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 6.7% (1 of 15) of reports.WarningH302 (53.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 15 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 1H-Imidazole, 1,1'-carbonothioylbis-Status: No longer Valid Update: 03-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/320051H-Imidazole, 1,1'-carbonothioylbis-: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| 有害性の概要 | An irritantHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (53.3%) |
| F | 9-21 |
| 水環境危害等級（WGK） | 3 |
| 税関コード | 29332900 |
| 危険文句（R） | 22-34 |
| 危険表示 | Xi |
| hazard_note | Irritant/Keep Cold/Moisture Sensitive |
| 安全措置（S） | 22-24/25-45-36/37/39-26 |
| 危険等級 | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
1,1'-Thiocarbonyldiimidazole (TCDI) is an imidazole compound that can be prepared by reacting thiophosphoryl chloride with two corresponding imidazoles. Its structure has two imidazole rings, and the imidazole groups can be rapidly displaced, making it a safer alternative to thiophosphoryl chloride. TCDI is used as an organic synthesis or chemical reaction reagent for the synthesis of thiosemicarbazones and thioamides. It is also used in the Corey-Winter olefin synthesis and in the Barton-McCombie deoxygenation reaction. In addition, it is the sulfur analogue of the peptide addition reagent carbodiimidazole (CDI), which is used to couple peptides.
使用
1,1'-Thiocarbonyldiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. It is also used to deoxygenate carboxylic monosaccharide analogues. Further, it is a useful reagent involved in biochemical synthesis. In addition to this, it is used to prepare 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol.
製法・合成法
純化方法
It forms yellow crystals on recrystallisation from tetrahydrofuran or by sublimation at 10-3torr (bath temperature 70-80o). It is hydrolysed by H2O and should be stored dry. [Staab & Walther Justus Liebigs Ann Chem 657 98 1962; Pullukat et al. Tetrahedron Lett 1953 1967, Hanessian et al. Can J Chem 65 1859 1987, Rajanbabu et al. J Am Chem Soc 111 1759 1989.] Thiochrome {2,7-dimethyl-5H -thiachromine-8-ethanol; 3,8-dimethyl-2-hydroxyethyl-5H -