1,1',3,3'-Tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide

Base Information

• Chemical Name: 1,1',3,3'-Tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide
• CAS No.: 3520-43-2
• Molecular Formula: C25H27Cl4IN4
• Molecular Weight: 652.22
• European Community (EC) Number: 812-509-2
• Wikidata: Q27123194
• Metabolomics Workbench ID: 58090
• ChEMBL ID: CHEMBL2074638
• Mol file: 3520-43-2.mol

Synonyms:5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolocarbocyanine;5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylimidacarbocyanine iodide;JC-1

Chemical Property of 1,1',3,3'-Tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide

Chemical Property:

• Melting Point: 275–278 ℃
• PSA: 18.67000
• LogP: 4.15720
• Storage Temp.: room temp
• Solubility.: Soluble in methanol, N,N-dimethyl formamide, dimethyl sulfoxide
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 652.00051
• Heavy Atom Count: 34
• Complexity: 625

Purity/Quality:

99% ^*data from raw suppliers

JC-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN1C2=CC(=C(C=C2[N+](=C1C=CC=C3N(C4=CC(=C(C=C4N3CC)Cl)Cl)CC)CC)Cl)Cl.[I-]
• Isomeric SMILES: CCN1C2=CC(=C(C=C2[N+](=C1/C=C/C=C3N(C4=CC(=C(C=C4N3CC)Cl)Cl)CC)CC)Cl)Cl.[I-]
• Description: JC-1 is a membrane-permeable cationic dye that is used to study mitochondrial integrity in the context of cellular apoptosis. It selectively enters mitochondria and changes fluorescence characteristics with alteration in mitochondrial transmembrane potential (ΔΨm). In healthy cells with a high mitochondrial ΔΨm, JC-1 forms complexes known as J-aggregates, which fluoresce red/orange and may be detected using FL2 settings by flow cytometry. A drop in ΔΨm, a very early event in apoptosis, results in JC-1 monomers, which fluoresce green (FL1 settings on flow cytometers). JC-1 may also be used with fluorescent microscopes or plate readers, using excitation at 520-570 nm and emission at 570-610 nm for J-aggregates and excitation at 485 nm and emission at 535 nm for monomers.
• Uses: A dual-emission potential-sensitive probe that can be used to measure mitochondrial membrane potential. JC-1 is a green-fluorescent monomer at low membrane potential. At higher potentials, JC-1 forms red-fluorescent "J-aggregates," which exhibit broad exc The cyanine dye JC-1 has been used to determine mitochondrial transmembrane potential.

Technology Process of 1,1',3,3'-Tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide

There total 6 articles about 1,1',3,3'-Tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide 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:

2-(2'-anilinoethenyl)-5,6-dichloro-1,3-diethylbenzimidazole (4751-25-1) → 5,6-dichloro-2-<1-<3-(5,6-dichloro-1,3-diethyl-2-benzimidazolylidene)propenyl>>-1,3-diethylbenzimidazolium iodide (3520-43-2,47729-63-5,440642-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / acetone / 4 h / Ambient temperature

2: 1.) NEt₃, pyridine, 2.) 25percent aq. KI / 1.) reflux, 2.) reflux

With pyridine; triethylamine; potassium iodide; In acetone;

DOI:10.1002/jlac.199719970107

Reference yield:

5,6-dichloro-1-ethyl-2-methyl benzimidazole (3237-62-5) → 5,6-dichloro-2-<1-<3-(5,6-dichloro-1,3-diethyl-2-benzimidazolylidene)propenyl>>-1,3-diethylbenzimidazolium iodide (3520-43-2,47729-63-5,440642-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 2 h / 160 °C

2: 1.) NEt₃, pyridine, 2.) 25percent aq. KI / 1.) reflux, 2.) reflux

With pyridine; triethylamine; potassium iodide;

DOI:10.1002/jlac.199719970107

Reference yield:

ethyl ester of p-toluenesulfonic acid (80-40-0) → 5,6-dichloro-2-<1-<3-(5,6-dichloro-1,3-diethyl-2-benzimidazolylidene)propenyl>>-1,3-diethylbenzimidazolium iodide (3520-43-2,47729-63-5,440642-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 2 h / 160 °C

2: 1.) NEt₃, pyridine, 2.) 25percent aq. KI / 1.) reflux, 2.) reflux

With pyridine; triethylamine; potassium iodide;

DOI:10.1002/jlac.199719970107

upstream raw materials:

ethyl iodide

5,6-dichloro-1-ethyl-2-methyl benzimidazole

ethyl ester of p-toluenesulfonic acid

2-(2'-anilinoethenyl)-5,6-dichloro-1,3-diethylbenzimidazole

Refernces

• 1、 Peng, Zheng-Hong,Geise,Zhou, Xiang-Feng,Peng, Bi-Xian,Carleer,Dommisse. "The structure of benzimidazole cyanine dyes, their spectroscopy and their performance in photographic emulsions". . p. 27 - 33. Retrieved 2007/10/03.