HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
((4-Trifluormethoxy)phenyl)-hydrazono)malononitril
FCCP · FCCCP · p-CF3O-CCP · FCCP, 10 mM in DMSO · Carbonyl Cyanide para Trifluoromethoxyphe · 4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILE · CARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZON · Trifluoromethoxy carbonylcyanide phenylhydrazone
Identifikatoren & physikalische Daten
| CAS No. | 370-86-5 |
|---|---|
| Summenformel | C10H5F3N4O |
| Durchschnittliche Molmasse | 254,17 g/mol |
| Monoisotopische Masse | 254,04154528 g/mol |
| SMILES | N#CC(C#N)=NNc1ccc(OC(F)(F)F)cc1 |
| InChIKey | BMZRVOVNUMQTIN-UHFFFAOYSA-N |
| PubChem CID | 3330 |
| ChEMBL | CHEMBL457504 |
| ChEBI | CHEBI:75458 |
| EC No. | 206-730-8 |
| DTXSID | DTXSID40190494 |
| Lokaler Name | ((4-Trifluormethoxy)phenyl)-hydrazono)malononitril |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 81,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 388 |
| LogP (Verteilungskoeffizient) | 3.68 |
| Schmelzpunkt | 174-175 °C (dec.)(lit.) |
| Siedepunkt | 293.3±50.0 °C(Predicted) |
| Dichte | 1.34±0.1 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | acetone: 20 mg/mL, clear, very deep greenish yellow |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 5.91±0.10(Predicted) |
| Farbe | yellow |
| BRN | 664446 |
| Stabilität | Stable for 2 years from date of purchase as supplied. Protect from exposure to moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months. |
| InChI | 1S/C10H5F3N4O/c11-10(12,13)18-9-3-1-7(2-4-9)16-17-8(5-14)6-15/h1-4,16H |
| InChIKey | BMZRVOVNUMQTIN-UHFFFAOYSA-N |
| SMILES | FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1 |
| CAS Datenbank | 370-86-5 |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (98.6%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P270, P272, P273, P280, P301+P316, P302+P352, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (98.6%) |
| 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) |
Anwendungen & Verwendung
Verwenden
FCCP is a potent uncoupler of oxidative phosphorylation in mitochondria that disrupts ATP synthesis by transporting protons across cell membranes. At 40 μM, FCCP induces complete depolymerization of microtubules by increasing intracellular pH via the disruption of the mitochondrial H+ gradient and by decreasing the stability of microtubules by impairing the binding of microtubule-associated proteins.[Cayman Chemical]