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Carbonyl cyanide p-trifluoromethoxyphenylhydrazone

HCID 3330
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
370-86-5
Standard SMILES
N#CC(C#N)=NNc1ccc(OC(F)(F)F)cc1
InChIKey
BMZRVOVNUMQTIN-UHFFFAOYSA-N
Molecular formula
C10H5F3N4O
Average molar mass
254.17 g/mol
Monoisotopic mass
254.04154528

Overview

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.

Names & identifiers

Preferred name
Carbonyl cyanide p-trifluoromethoxyphenylhydrazone
IUPAC
2-[[4-(trifluoromethoxy)phenyl]hydrazinylidene]propanedinitrile
English name
FCCP
Molecular formula
C10H5F3N4O
Molecular weight
254.17

Names & synonyms

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
Show more names
FCCCPp-CF3O-CCPFCCP, 10 mM in DMSOCarbonyl Cyanide para Trifluoromethoxyphe4-(TRIFLUOROMETHOXY)PHENYLAZOMALONONITRILECARBONOYLCYANID-4-TRIFLUORMETHOXYPHENYL-HYDRAZONTrifluoromethoxy carbonylcyanide phenylhydrazoneMESOXALONITRILE 4-TRIFLUOROMETHOXYPHENYLHYDRAZONECarbonylcyanide-p-trifluoromethoxuphenylhydrazone
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

Properties

Computed structural properties

XLogP
3.7
Topological polar surface area
81.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
8
Rotatable bonds
3
Heavy atoms
18
Formal charge
0
Complexity
388

Experimental & physicochemical properties

LogP3.68

Physicochemical properties

Melting point
174 · 174-175 °C (dec.)(lit.)
Boiling point
293.3 · 293.3±50.0 °C(Predicted)
Density
1.34 · 1.34±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
20 mg/mL, · acetone: 20 mg/mL, clear, very deep greenish yellow
form
powder
pka
5.91 · 5.91±0.10(Predicted)
color
yellow
Appearance
bright yellow crystals
BRN
664446 · 664446
Stability
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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (98.6%)

Toxicology

Treatment · 1 item

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 item

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 item

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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.
Applications · 2 items

DescriptionFCCP (370-86-5) is an extremely potent uncoupler of mitochondrial oxidative phosphorylation (IC50 = 20 nM).1 Induces apoptosis in a variety of cell lines.2 Inhibits wild type and mutant beta-amyloid production in embryonic kidney 293 cells expressing either wild-type or “Swedish” mutant APP.3 An important tool for inhibiting mitochondrial membrane potential.2,4 Cell permeable.

UsesFCCP 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]

Suppliers100 total

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0731-88532326 13319508186 · [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

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
370-86-5
PubChem CID
3330
DTXSID
DTXSID40190494
ChEMBL
CHEMBL457504
ChEBI
CHEBI:75458
UNII
SQR3W2FLV5
EC Number
206-730-8
Nikkaji
J39.578A
InChIKey
BMZRVOVNUMQTIN-UHFFFAOYSA-N
SMILES
FC(F)(F)Oc1ccc(N\N=C(/C#N)C#N)cc1
CAS DataBase Reference
370 · 370-86-5
FDA UNII
3 W2FLV5 · SQR3W2FLV5
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H314-H317-H413
Precautionary statements
260 · P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
PPE
2 · Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes
T,Xi
Risk Statements
25 · 25-43
Safety Statements
36 · 36/37-45
RIDADR
2811 · UN 2811 6.1/PG 2
WGK Germany
3 · 3
RTECS
5775000 · FG5775000
Hazard Note
Irritant
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
2928009090 · 2928009090
Storage Class
6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 4Eye Dam. 1Skin Corr. 1BSkin Sens. 1
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).

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
FG5775000
ridadr
UN 2811 6.1/PG 2
hs_code
2928009090
risk_code
25-43
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
T,Xi
hazard_note
Irritant
safety_code
36/37-45
hazard_class
6.1(a)
Storage Class
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group
II
Hazard statements
H302-H314-H317-H413
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 4Eye Dam. 1Skin Corr. 1BSkin Sens. 1
Precautionary statements
P260-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
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广东翁江化学试剂有限公司0751-2886766 13927870850 · [email protected]

Additional notes

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