2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril
TCNQ · TETRACYANOQUINODIMETHANE · Tetracyanoquinodimethan · Tetracyano p-Quinone Dimethane · 2,2'-(Cyclohexa-2,5-diene-1,4-diylidene)dimalononitrile · TIMTEC-BB SBB000435 · 7,7,8,8-Tetracyanoqu · tetracyano-quinodimetha
Identifikatoren & physikalische Daten
| CAS No. | 1518-16-7 |
|---|---|
| Summenformel | C12H4N4 |
| Durchschnittliche Molmasse | 204,19 g/mol |
| Monoisotopische Masse | 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 |
| Lokaler Name | 2,2'-(2,5-Cyclohexadien-1,4-diyli-den)bismalononitril |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 95,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 535 |
| Stoffklassen | Nitrogen Compounds -> Nitriles |
| SpringerMaterials Properties | Band gap energy |
| Physical Description | Green crystalline solid[Alfa Aesar MSDS] |
| Schmelzpunkt | 287-289 °C (dec.) (lit.) |
| Siedepunkt | 332.67°C (rough estimate) |
| Dichte | 1.3596 (rough estimate) |
| Brechungsindex | 1.5000 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| Farbe | Orange-brown to green |
| Löslichkeit | insoluble |
| BRN | 611604 |
| Stabilität | Stable. Incompatible with strong acids, strong bases, strong reducing agents, strong oxidizing agents. |
| 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 Datenbank | 1518-16-7(CAS DataBase Reference) |
| NIST chemische Informationen | Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis-(1518-16-7) |
| EPA chemische Informationen | Propanedinitrile, 2,2'-(2,5-cyclohexadiene-1,4-diylidene)bis- (1518-16-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | 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. |
|---|---|
| Regulatorische Informationen | 7,7,8,8-Tetracyanoquinonedimethane: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | 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) |
| Gesundheitliche Auswirkungen | 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) |
| Expositionspfade | Oral (L96)inhalation (L96)dermal (L96) |
| Toxizitätsübersicht | 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). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3276 |
| Zollcode | 29269095 |
| RTECS-Nr. | GU4850000 |
| R-Sätze (R) | 22-20/21/22-23/24/25 |
| Gefahrensymbole | Xn,Xi,T |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 22-24/25-36/37-26-36-45 |
| Gefahrenklasse | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral |
| Verpackungsgruppe | II |
| Lagerklasse | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
Anwendungen & Verwendung
Beschreibung
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].
History
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].
Verwenden
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.