(3-Chlorophenyl)hydrazonomalononitrile

Base Information

• Chemical Name: (3-Chlorophenyl)hydrazonomalononitrile
• CAS No.: 555-60-2
• Deprecated CAS: 81693-28-9,208707-97-5
• Molecular Formula: C9H5 Cl N4
• Molecular Weight: 204.619
• Hs Code.: 2928000090
• European Community (EC) Number: 209-103-7
• NSC Number: 88124
• UNII: 4D4NW27CG5
• DSSTox Substance ID: DTXSID7040990
• Nikkaji Number: J13.752I
• Wikipedia: Carbonyl_cyanide_m-chlorophenyl_hydrazone
• Wikidata: Q2720515
• Metabolomics Workbench ID: 53030
• ChEMBL ID: CHEMBL224214
• Mol file: 555-60-2.mol

Synonyms:4-Chlorophenylhydrazone, Carbonylcyanide;Carbonyl Cyanide m Chlorophenyl Hydrazone;Carbonyl Cyanide m-Chlorophenyl Hydrazone;Carbonyl Cyanide meta Chlorophenyl Hydrazone;Carbonyl Cyanide meta-Chlorophenyl Hydrazone;Carbonylcyanide 4 Chlorophenylhydrazone;carbonylcyanide 4-chlorophenylhydrazone;CCCP;Propanedinitrile, ((3-chlorophenyl)hydrazono)-

Chemical Property of (3-Chlorophenyl)hydrazonomalononitrile

Chemical Property:

• Appearance/Colour: yellow to orange powder
• Vapor Pressure: 0.000363mmHg at 25°C
• Melting Point: 170-175 °C
• Refractive Index: 1.6110 (estimate)
• Boiling Point: 318.3 °C at 760 mmHg
• PKA: 6.00±0.10(Predicted)
• Flash Point: 146.3 °C
• PSA: 71.97000
• Density: 1.26 g/cm³
• LogP: 2.22806
• Storage Temp.: 2-8°C
• Solubility.: methanol: 10 mg/mL, clear, very deep yellow
• Water Solubility.: Insoluble in water. Soluble in DMSO (5 mg/ml), ethanol (1 mg/ml) and methanol (10 mg/ml).
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 204.0202739
• Heavy Atom Count: 14
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

CCCP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC(=C1)Cl)NN=C(C#N)C#N
• Description: CCCP is a protonophore mitochondrial uncoupler that increases membrane permeability to protons, leading to a disruption in the mitochondrial membrane potential. It inhibits mitochondrial respiration and ATPase activity when used at concentrations of 110 and 35 nM, respectively. CCCP inhibits activation of stimulation of interferon genes (STING), decreasing the expression of downstream STING targets, including IFN-β, TBK1, and IRF3 when used at a concentration of 50 μM in RAW 264.7 cells. It induces mitochondrial fission in a manner dependent on the GTPase Drp1. CCCP (4 mg/kg) increases body temperature as well as left ventricular systolic and diastolic dimensions and decreases fractional shortening in rats. It also increases myocardial glucose and fatty acid uptake in rats.
• Uses: Carbonyl cyanide 3-chlorophenylhydrazone is a widely used uncoupler of oxidative phosphorylation. Carbonyl cyanide 3-chlorophenylhydrazone (CCCP) has been used:in the inhibition of efflux pump in clinical Pseudomonas aeruginosato inhibit oxidative phosphorylation activity of mitochondria in human Beas-2B bronchial epithelial cellsto prepare carbonyl cyanide m-chlorophenylhydrazone solution for oxidative and mitochondrial stress assay and mitophagy induction in Caenorhabditis elegans

Technology Process of (3-Chlorophenyl)hydrazonomalononitrile

There total 4 articles about (3-Chlorophenyl)hydrazonomalononitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

3-chloro-aniline (108-42-9) + malononitrile (109-77-3) → carbonyl cyanide m-chlorophenylhydrazone (555-60-2)

Guidance literature:

3-chloro-aniline; With hydrogenchloride; sodium nitrite; In water; for 1.5h; Cooling with ice;

malononitrile; With sodium acetate; In water; at 0 ℃; for 2h;

DOI:10.1039/d0ra03124k

Reference yield:

1,1-dicyanoethylene (922-64-5) + 3-chloro-aniline (108-42-9) → carbonyl cyanide m-chlorophenylhydrazone (555-60-2)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water;

DOI:10.1016/j.molstruc.2021.129960

Reference yield:

alpha-(2-(2,2-dicyanovinyl)-2-(3-chlorophenyl)hydrazono)malononitrile (68657-31-8) → carbonyl cyanide m-chlorophenylhydrazone (555-60-2)

Guidance literature:

With triethylamine;

DOI:10.1021/jo01328a013

upstream raw materials:

alpha-(2-(2,2-dicyanovinyl)-2-(3-chlorophenyl)hydrazono)malononitrile

3-chloro-aniline

malononitrile

1,1-dicyanoethylene

Downstream raw materials:

O,O,O,O-tetraisopropyl pyrophosphorotrithioate

C₉H₇ClN₄S

Refernces

• 1、 Lu, Jun,Lu, Xueer,Tang, Wenjian,Xu, Yingying,Zhang, Jing,Zhang, Ziwen. "Effect of new carbonyl cyanide aromatic hydrazones on biofilm inhibition against methicillin resistant: Staphylococcus aureus". . p. 17854 - 17861. Retrieved 2020/06/17.
• 2、 Le Corre, Laurent,Dasso Lang, Maria Chiara,Garbay, Christiane,Gravier-Pelletier, Christine,Busca, Patricia,Ethève-Quelquejeu, Mélanie,Braud, Emmanuelle. "Synthesis of Multifunctionalized 2-Iminothiazolidin-4-ones and Their 2-Arylimino Derivatives". . p. 4569 - 4579. Retrieved 2016/12/14.