7,7,8,8-テトラシアノキノジメタン
7,7,8,8-テトラシアノキノジメタン · 2,2'-(シクロヘキサ-2,5-ジエン-1,4-ジイリデン)ビス(プロパンジニトリル) · 2,2'-(2,5-シクロヘキサジエン-1,4-ジイリデン)ビス(プロパンジニトリル) · 2,2'-(2,5-シクロヘキサジエン-1,4-ジイリデン)ビス(マロノニトリル) · 1,4-ビス(ジシアノメチレン)-2,5-シクロヘキサジエン · テトラシアノキノジメタン · 3,6-ビス(ジシアノメチレン)-1,4-シクロヘキサジエン · 2,2'-(2,5-シクロヘキサンジエン-1,4-ジイリデン)ビス(プロパンジニトリル)
識別子と物理属性
| CAS No. | 1518-16-7 |
|---|---|
| 分子式 | C12H4N4 |
| 平均分子量 | 204.19 g/mol |
| 単同位体質量 | 204.04359613 g/mol |
| SMILES | N#CC(C#N)=c1ccc(=C(C#N)C#N)cc1 |
| InChIKey | PCCVSPMFGIFTHU-UHFFFAOYSA-N |
| PubChem CID | 73697 |
| ChEBI | CHEBI:52445 |
| EC No. | 216-174-8 |
| DTXSID | DTXSID5061748 |
| 現地名 | 7,7,8,8-テトラシアノキノジメタン |
化学・物理的性質
| XLogP | 1 |
|---|---|
| 極性表面積 | 95.2 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 0 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 535 |
| 物質分類 | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | Band gap energy |
| Physical Description | Green crystalline solid[Alfa Aesar MSDS] |
| 融点 | 287-289 °C (dec.) (lit.) |
| 沸点 | 332.67°C (rough estimate) |
| 密度 | 1.3596 (rough estimate) |
| 屈折率 | 1.5000 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 結晶性粉末 |
| 色 | オレンジブラウンからグリーン |
| 溶解度 | 不溶性 |
| BRN | 611604 |
| 安定性 | 安定。強酸、強塩基、強還元剤、強酸化剤とは相容れない。 |
| InChI | InChI=1S/C12H4N4/c13-5-11(6-14)9-1-2-10(4-3-9)12(7-15)8-16/h1-4H |
| InChIKey | PCCVSPMFGIFTHU-UHFFFAOYSA-N |
| SMILES | C1(=C(C#N)C#N)C=CC(=C(C#N)C#N)C=C1 |c:8,t:0| |
| CAS データベース | 1518-16-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7) |
| EPAの化学物質情報 | Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7) |
化学的特性
orange to green crystalline powder
安全性と法規制
| GHS 分類 | DangerH301+H311+H331 (87%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P261, P262, P264, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P317, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | 7,7,8,8-Tetracyanoquinonedimethane: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Intravenous LD50 (mouse) = 56 mg/kg[RTECS] May cause irritationHarmful by ingestion and skin absorptionToxic by inhalation[Alfa Aesar MSDS] See NITRILES. |
| Hazard Classes and Categories | Acute Tox. 3 (89.1%) |
| Protective Action Criteria (PAC) | 0.18 [mg/m3]2.0 [mg/m3]12 [mg/m3] |
| Treatment | Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97) |
| 健康影響 | Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97) |
| 暴露経路 | Oral (L96)inhalation (L96)dermal (L96) |
| 毒性の概要 | Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) |
| Signs and Symptoms | Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97) |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | GU4850000 |
| 輸送番号（UN） | 3276 |
| 税関コード | 29269095 |
| 危険文句（R） | 22-20/21/22-23/24/25 |
| 化審法 | (3)-1798 |
| 危険表示 | Xn,Xi,T |
| hazard_note | Irritant |
| 安全措置（S） | 22-24/25-36/37-26-36-45 |
| 危険等級 | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral |
| 包装等級 | II |
| 毒劇物取締法 | 劇物 |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
用途
解説
2,2′-(2,5-cyclohexadiene-1,4-diylidene)bispropanedinitrile．C12H4N4(204.19)．略称TCNQ．シクロヘキサン-1,4-ジオンとマロノニトリルとを縮合させて1,4-ビス(ジシアノメチレン)シクロヘキサンとし，ついで臭素化，脱臭化水素して合成する．"橙色の結晶．分解点297～298 ℃．アセトニトリル，ジオキサン，THFなどに可溶．強力な電子受容体として分子錯体を形成するほか，多数の単純および複雑陰イオンラジカル塩，M＋ (TCNQ)n(n ＝ 1，4/3，3/2，2)などを与え，高電導性のものも多い．電導性および光電導性複合材料として，ケミカルコンデンサーなどの電子材料，電子写真用感光材料に用いられる．[CAS 1518-16-7]森北出版「化学辞典（第2版）
説明
7,7,8,8-tetracyanoquinodimethane (TCNQ), with a LUMO at 4.5 eV, is known for the charge-transfer salts formed by its radical anion TCNQ inphotovoltaic, light-emitting diodes, and organic field-effect transistordevices. TCNQ and its derivativeshave been used as dopants, leading to an increase in hole mobility or to the lowering of injectionbarriers. One classic example of such is the treatment of tetrathiafulvene (TTF), an electron donor with TCNQ. TFF and TCNQ form an ion pair, the TTF-TCNQ complex. This process of doping leads to the crystallisation of the ion pair into a one-dimensionally stacked polymer. This polymer consists of segregated stacks of cations and anions of the donors and the acceptors, respectively. The complex crystal is an organic semiconductor that exhibits metallic electric conductivity [1, 2].
来歴
The first report on the electrical conductivity in an organic solid appeared in 1954, namely, a perylene—bromine complex with a room-temperature conductivity of 0.1 S cm1. In 1960, the organic acceptor Tetracyanoquinodimethane (TCNQ; 7,7,8,8-Tetracyanoquinodimethane) was synthesized, as well as a great number of its conducting charge-transfer complexes and radical ion salts. In the 1970s, the organic donor TTF led to the first organic metal TTF-TCNQ. Its room-temperature conductivity (500 S cm1) increases with a decrease in the temperature to the value of 6000 S cm1 at 60 K, where a metal-insulator transition occurs[1].
使用
7,7,8,8-Tetracyanoquinodimethane is an electron-acceptor molecule used to form charge-transfer superconductors. It is an effective catalyst used for the -chlorination of carboxylic acids using chlorosulfonic acid; the presence of TCNQ suppresses competing free-radical chlorination.
一般的な説明
7,7,8,8-Tetracyanoquinodimethane (TNCQ) is a strong electron acceptor as it has four cyano groups and π-conjugation bonds that form charge transferring chains and ion radical salts which are mainly used as p-dopants for the fabrication of a variety of semiconductor applications.