N-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide

• ChemBase ID: 105919
• Molecular Formular: C9H5ClN4
• Molecular Mass: 204.6158
• Monoisotopic Mass: 204.02027386
• SMILES: Clc1cc(NN=C(C#N)C#N)ccc1
• Canonical SMILES: N#CC(=NNc1cccc(c1)Cl)C#N
• InChI: InChI=1S/C9H5ClN4/c10-7-2-1-3-8(4-7)13-14-9(5-11)6-12/h1-4,13H
• InChIKey: UGTJLJZQQFGTJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-chlorophenyl)-1-cyanomethanecarbohydrazonoyl cyanide
• IUPAC Traditional name: CCCP
• Synonyms: m-Cl-CCP; CCCP; Mesoxalonitrile 3-chlorophenylhydrazone; Carbonyl cyanide 3-chlorophenylhydrazone; CARBONYL CYANIDE m-CHLOROPHENYL HYDRAZONE; 羰基氰酯-3-氯苯基腙

Database IDs

• CAS Number: 555-60-2
• EC Number: 209-103-7
• MDL Number: MFCD00001848
• Beilstein Number: 1842102
• PubChem SID: 24892523; 162088992
• PubChem CID: 2603
• CHEBI ID: 3259
• CHEMBL: 224214
• Chemspider ID: 2504
• KEGG ID: C11164
• MeSH Name: CCCP
• Wikipedia Title: Carbonyl_cyanide_m-chlorophenyl_hydrazone

CALCULATED PROPERTIES

• Acid pKa: 10.596134
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.193605
• LogD (pH = 7.4): 3.193337
• Log P: 3.1936085
• Molar Refractivity: 54.2857 cm^3
• Polarizability: 19.314234 Å^3
• Polar Surface Area: 71.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble100 mM; methanol: soluble10 mg/mL, clear, very deep yellow
• Apperance: yellow to orange powder
• Melting Point: 170-175 °C (dec.); 175- 177°C; ca 175°C dec.

Safety Information

• Storage Condition: 0°C
• RTECS: FG5600000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811; UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 23/24/25-36/37/38; 25-36/37/38
• Safety Statements: 26-36/37-45; 36/37-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H330-H335; H301-H311-H315-H319-H331-H335; H301-H315-H319-H335
• GHS Precautionary statements: P260-P280-P284-P305 + P351 + P338-P310; P261-P280-P301 + P310-P305 + P351 + P338-P311; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97% (TLC); ≥98.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C9H5ClN4

DETAILS

MP Biomedicals - 02195094

Uncoupler of oxidative phosphorylation in mitochondrial systems

Sigma Aldrich - C2759

包装
1 g in glass bottle
100, 250 mg in glass bottle
Biochem/physiol Actions
Protonophore (H+ ionophore) and uncoupler of oxidative phosphorylation in mitochondria. Shown to have a number of effects on cellular calcium. Inhibits secretion of hepatic lipase and partially inhibits the pH gradient-activated Cl- uptake and Cl-/Cl- exchange activities in brush-border membrane vesicles.

Sigma Aldrich - 21855

Other Notes
One of the most potent uncouplers of oxidative phosphorylation1

REFERENCES

• D. Shiun, Shu-I Tu, Biochemistry , 17 : 2245 (1978).
• Heytler, P.G. and Prichard, W.W., Biochem. Biophys. Res. Comm. , 7 : 272 (1962).
• Uncoupler of oxidative phosphorylation: Biochem. Biophys. Acta, 394 145 (1975); Biochemistry, 17, 2245 (1978).