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((4-Trifluormethoxy)phenyl)-hydrazono)malononitril

Carbonyl cyanide p-trifluoromethoxyphenylhydrazone

HCID 3330
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Grundinformationen

CAS
370-86-5
Standard-SMILES
N#CC(C#N)=NNc1ccc(OC(F)(F)F)cc1
InChIKey
BMZRVOVNUMQTIN-UHFFFAOYSA-N
Summenformel
C10H5F3N4O
Durchschnittliche Molmasse
254,17 g/mol
Monoisotopische Masse
254,04154528

Überblick

Carbonyl cyanide p-trifluoromethoxyphenylhydrazone is a hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group. It has a role as a geroprotector, an ATP synthase inhibitor and an ionophore. It is a nitrile, an aromatic ether, an organofluorine compound and a hydrazone. It is functionally related to a hydrazonomalononitrile.

Namen und Bezeichner

Bevorzugter Name
Carbonyl cyanide p-trifluoromethoxyphenylhydrazone
IUPAC
2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile
Lokaler Name
((4-Trifluormethoxy)phenyl)-hydrazono)malononitril
Englischer Name
FCCP
Summenformel
C10H5F3N4O
Molmasse
254.17

Namen und Synonyme

FCCP370-86-5Carbonyl cyanide p-trifluoromethoxyphenylhydrazone2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrilePropanedinitrile, ((4-(trifluoromethoxy)phenyl)hydrazono)-SQR3W2FLV5Mesoxalonitrile, (p-(trifluoromethoxy)phenyl)hydrazonePropanedinitrile, [[4-(trifluoromethoxy)phenyl]hydrazono]-Carbonyl cyanide, 4-trifluoromethoxyphenylhydrazone((4-(Trifluoromethoxy)phenyl)hydrazono)malononitrileCHEBI:754581-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide
Weitere Namen anzeigen
FCCCPp-CF3O-CCPFCCP, 10 mM in DMSOCarbonyl Cyanide para Trifluoromethoxyphe4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILECARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZONTrifluoromethoxy carbonylcyanide phenylhydrazoneMESOXALONITRILE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONECarbonylcyanide-p-trifluoromethoxuphenylhydrazone

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,7
Polarare Oberfläche (TPSA)
81,2 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
3
Schwere Atome
18
Formalladung
0
Komplexität
388

Experimentelle und physikochemische Eigenschaften

LogP3.68

Physikochemische Eigenschaften

Schmelzpunkt
174 · 174-175 °C (dec.)(lit.)
Siedepunkt
293.3 · 293.3±50.0 °C(Predicted)
Dichte
1.34 · 1.34±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
20 mg/mL, · acetone: 20 mg/mL, clear, very deep greenish yellow
Aggregatzustand
powder
pka
5.91 · 5.91±0.10(Predicted)
Farbe
yellow
BRN
664446 · 664446
Stabilität
2 years · 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

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H301 (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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (98.6%)

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Health Effects · 1 Eintrag

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)

Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 Eintrag

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)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

MeSH Pharmacological ClassificationChemical agents that increase the permeability of CELL MEMBRANES to PROTONS.
Anwendungen · 1 Eintrag

VerwendenFCCP 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]

Anbieter100 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海乾豪生物科技有限公司

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID40190494Carbonyl cyanide 4-trifluoromethoxyphenylhydrazoneCyanide p-Trifluoromethoxyphenylhydrazone, Carbonylp-Trifluoromethoxyphenylhydrazone, Carbonyl Cyanide(4-(Trifluoromethoxy)phenyl)hydrazonopropanedinitrile{[4-(trifluoromethoxy)phenyl]hydrazono}malononitrile2-((4-(TRIFLUOROMETHOXY)PHENYL)HYDRAZINYLIDENE)PROPANEDINITRILE1-cyano-N-(4-(trifluoromethoxy)phenyl)methanecarbohydrazonoyl cyanide

Datenbank-Bezeichner

CAS
370-86-5
PubChem CID
3330
DTXSID
DTXSID40190494
ChEMBL
CHEMBL457504
ChEBI
CHEBI:75458
UNII
SQR3W2FLV5
EC Number
206-730-8
Nikkaji
J39.578A
SMILES
FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1
CAS Datenbank
370 · 370-86-5
Signs and SymptomsCyanide 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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1/PG 2
hs_code
2928009090
RTECS-Nr.
FG5775000
risk_code
25-43
hazard_code
T,Xi
hazard_note
Irritant
safety_code
36/37-45
hazard_class
6.1(a)
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 4Eye Dam. 1Skin Corr. 1BSkin Sens. 1
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Ergänzende Hinweise

DefinitionChEBI: A hydrazone that is hydrazonomalononitrile in which one of the hydrazine hydrogens is substituted by a p-trifluoromethoxyphenyl group.