3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt

Base Information

• Chemical Name: 3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt
• CAS No.: 146368-11-8
• Molecular Formula: C₃₃H₄₀N₂O₈S₂
• Molecular Weight: 656.821
• Hs Code.: 29339900
• Mol file: 146368-11-8.mol

Synonyms:146368-11-8;3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt;(2E)-2-[(2E,4E)-5-[1-(5-carboxypentyl)-3,3-dimethyl-5-sulfoindol-1-ium-2-yl]penta-2,4-dienylidene]-1-ethyl-3,3-dimethylindole-5-sulfonate;Cy5;2-(5-(1-(5-Carboxypentyl)-3,3-dimethyl-5-sulfoindolin-2-ylidene)penta-1,3-dien-1-yl)-1-ethyl-3,3-dimethyl-3H-indol-1-ium-5-sulfonate;AC-35417;AS-75266;2-[(1E,3E)-5-[(2E)-1-(5-carboxypentyl)-3,3-dimethyl-5-sulfo-2,3-dihydro-1H-indol-2-ylidene]penta-1,3-dien-1-yl]-1-ethyl-3,3-dimethyl-3H-indol-1-ium-5-sulfonate;3H-Indolium,2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-,innersalt

Chemical Property of 3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt

Chemical Property:

• PSA: 174.71000
• LogP: 7.51540
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 656.22260859
• Heavy Atom Count: 45
• Complexity: 1430

Purity/Quality:

98%,99%, ^*data from raw suppliers

CY5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCN1C2=C(C=C(C=C2)S(=O)(=O)[O-])C(C1=CC=CC=CC3=[N+](C4=C(C3(C)C)C=C(C=C4)S(=O)(=O)O)CCCCCC(=O)O)(C)C
• Isomeric SMILES: CCN\1C2=C(C=C(C=C2)S(=O)(=O)[O-])C(/C1=C\C=C\C=C\C3=[N+](C4=C(C3(C)C)C=C(C=C4)S(=O)(=O)O)CCCCCC(=O)O)(C)C
• Uses: CY5 is a photoswitchable cyanine dye. The photoswitching mechanism was investigated using thiol agents and it was concluded that photoconversion into the dark state is pH and thiol dependent and the dark state product is a cyanine-thiol adduct.

Technology Process of 3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt

There total 12 articles about 3H-Indolium, 2-[5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadien-1-yl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt 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: 22.0%

1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate (146368-08-3) + C24H26N2O4S (146397-21-9) → 1-(5-carboxypentyl)-2-[3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)-2,3-dihydro-1H-indol-2-yliden]-1,3-pentadienyl-3,3-dimethyl-3H-indolium-5-sulfonate (146368-11-8,209340-51-2,917979-28-3)

Guidance literature:

With pyridine; at 60 ℃; for 4h;

Reference yield: 22.0%

1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate (146368-08-3) + C22H24N2O3S → 1-(5-carboxypentyl)-2-[3,3-dimethyl-5-sulfo-1-(4-sulfobutyl)-2,3-dihydro-1H-indol-2-yliden]-1,3-pentadienyl-3,3-dimethyl-3H-indolium-5-sulfonate (146368-11-8,209340-51-2,917979-28-3)

Guidance literature:

With pyridine; at 60 ℃; for 4h;

Reference yield:

1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate (146368-08-3) + malonaldehyde bis(phenylimine) monohydrochloride (51143-32-9,123071-42-1,137692-98-9) + 1-Ethyl-2,3,3-Trimethylindolenineninium 5-Sulfone (146368-07-2) → 1-(5-carboxypentyl)-2-[(1E,3E)-5-(1-ethyl-3,3-dimethyl-5-sulfo-1,3-dihydro-2H-indol-2-ylidene)-1,3-pentadienyl]-3,3-dimethyl-5-sulfo-3H-indolium (917979-28-3,209340-51-2,146368-11-8)

Guidance literature:

malonaldehyde bis(phenylimine) monohydrochloride; 1-Ethyl-2,3,3-Trimethylindolenineninium 5-Sulfone; With acetic anhydride; acetic acid; for 4h; Heating / reflux;

1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate; With pyridine; for 3h; Heating / reflux;

upstream raw materials:

1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate

malonaldehydebis(dimethylacetal)

1-Ethyl-2,3,3-Trimethylindolenineninium 5-Sulfone

6-bromohexanoic acid

Downstream raw materials:

Cy 5

Cy₅-NHS

C₃₇H₄₃N₃O₁₀S₂

3H-indolium-2-[(1E,3E,5E)-5-[1-(5-carboxypentyl)-1,3-dihydro-3,3-dimethyl-5-sulfo-2H-indol-2-ylidene]-1,3-pentadienyl]-1-ethyl-3,3-dimethyl-5-sulfo-, inner salt, succinimidyl ester

Refernces

• 1、 -. "Cyanine compound for labeling biomolecule and preparation method thereof". Page/Page column 19; 20. . Retrieved 2014/05/25.
• 2、 Jiang, Lin-Ling,Dou, Li-Fang,Li, Bao-Lin. "An efficient approach to the synthesis of water-soluble cyanine dyes using poly(ethylene glycol) as a soluble support". . p. 5825 - 5829. Retrieved 2008/02/09.