1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide

• ChemBase ID: 93283
• Molecular Formular: C10H5F3N4O
• Molecular Mass: 254.1681096
• Monoisotopic Mass: 254.04154546
• SMILES: N(c1ccc(cc1)OC(F)(F)F)N=C(C#N)C#N
• Canonical SMILES: N#CC(=NNc1ccc(cc1)OC(F)(F)F)C#N
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide
• IUPAC Traditional name: 1-cyano-N-[4-(trifluoromethoxy)phenyl]methanecarbohydrazonoyl cyanide
• Synonyms: {2-[4-(Trifluoromethoxy)phenyl]hydrazinylidene}propane-1,3-dinitrile; 4-[2-(Dicyanomethylidene)hydrazino]-alpha,alpha,alpha-trifluoroanisole; 2-{2-[4-(Trifluoromethoxy)phenyl]hydrazono}malononitrile 95+%; Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone; 2-{2-[4-(trifluoromethoxy)phenyl]hydrazono}malononitrile; FCCP; Mesoxalonitrile 4-trifluoromethoxyphenylhydrazone; Carbonyl cyanide 4-(trifluoromethoxy)phenylhydrazone; CARBONYL CYANIDE p-TRIFLUOROMETHOXYPHENYL HYDRAZONE; Carbonyl cyanide-p-trifluoromethoxyphenylhydrazone; 羰基氰对三氟甲氧基苯腙; 碳酰氰 4-(三氟甲氧基)苯腙

Database IDs

• CAS Number: 370-86-5
• EC Number: 206-730-8
• MDL Number: MFCD00009699
• Beilstein Number: 664446
• PubChem SID: 162079968; 24892549
• PubChem CID: 3330
• CHEMBL: 457504
• Chemspider ID: 3213
• MeSH Name: FCCP
• Wikipedia Title: Carbonyl_cyanide-p-trifluoromethoxyphenylhydrazone

CALCULATED PROPERTIES

• Acid pKa: 11.201626
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.0206747
• LogD (pH = 7.4): 4.020608
• Log P: 4.020675
• Molar Refractivity: 52.5512 cm^3
• Polarizability: 19.499113 Å^3
• Polar Surface Area: 81.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 95% ethanol: soluble; acetone: soluble20 mg/mL, clear, very deep greenish-yellow
• Apperance: yellow powder
• Melting Point: 174-175 °C (dec.)(lit.); 174-175(dec.)°C

Safety Information

• Storage Condition: 0°C
• Storage Warning: Toxic/Keep Cold
• RTECS: FG5775000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25-43
• Safety Statements: 36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317-H413
• GHS Precautionary statements: P280-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC); ≥99.0% (HPLC); 95%; 97%
• Quality Level: PREMIUM
• Linear Formula: CF3OC6H4NHN=C(CN)2

DETAILS

MP Biomedicals - 02105646

Uncoupler of oxidative phosphorylation.

Sigma Aldrich - C2920

Biochem/physiol Actions
FCCP is a protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. It is capable of depolarizing plasma and mitochondrial membranes. FCCP has been shown to have a number of effects on cellular calcium. It also is reported to inhibit a background K+ current and induce a small inward current, reduce pH by 0.1 unit, and induce a rise of intracellular [Na+]. FCCP stimulates Mg2+-ATPase activity, inhibits β-amyloid production, and mimics the effect of selective glutamate agonist N-methyl-D-aspartate (NMDA) on mitochondrial superoxide production.

Sigma Aldrich - 21857

Other Notes
Uncoupler of oxidative phosphorylation1