Sodium 2-(7-(3,3-dimethyl-1-(4-sulfonatobutyl)benz(e)indolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-1-(4-sulfonatobutyl)benz[e]indolinium

Base Information

• Chemical Name: Sodium 2-(7-(3,3-dimethyl-1-(4-sulfonatobutyl)benz(e)indolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-1-(4-sulfonatobutyl)benz[e]indolinium
• CAS No.: 3599-32-4
• Molecular Formula: C43H47N2NaO6S2
• Molecular Weight: 774.978
• Hs Code.: 32129000
• European Community (EC) Number: 222-751-5
• DSSTox Substance ID: DTXSID2023145
• Wikipedia: Indocyanine_green
• NCI Thesaurus Code: C65913
• RXCUI: 5775
• Mol file: 3599-32-4.mol

Synonyms:1H-Benz[e]indolium,2-[7-[1,1-dimethyl-3-(4-sulfobutyl)benz[e]indolin-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,hydroxide, inner salt, sodium salt (8CI);1H-Benz[e]indolium,2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,hydroxide, inner salt, sodium salt;1H-Benz[e]indolium,2-[7-[1,3-dihydro-1,1-dimethyl-3-(4-sulfobutyl)-2H-benz[e]indol-2-ylidene]-1,3,5-heptatrienyl]-1,1-dimethyl-3-(4-sulfobutyl)-,inner salt, sodium salt (9CI);4,5-Benzoindotricarbocyanine;Cardio Green;HWDIndocyanine Green;ICG;IR 125;Indocyanin green;NK 2612;Opthagreen;SO 270;Ujoviridin;Wofaverdin;

Chemical Property of Sodium 2-(7-(3,3-dimethyl-1-(4-sulfonatobutyl)benz(e)indolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-1-(4-sulfonatobutyl)benz[e]indolinium

Chemical Property:

• Appearance/Colour: green to brown crystals or crystalline powder
• Melting Point: 235 °C
• Boiling Point: 157oC
• PSA: 137.41000
• LogP: 10.55570
• Storage Temp.: Amber Vial, Refrigerator
• Solubility.: H2O: soluble1mg/mL
• Water Solubility.: slightly soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 774.27732385
• Heavy Atom Count: 54
• Complexity: 1520

Purity/Quality:

99%, ^*data from raw suppliers

Indocyanine green ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Dyes -> Carbocyanine Dyes
• Canonical SMILES: CC1(C(=[N+](C2=C1C3=CC=CC=C3C=C2)CCCCS(=O)(=O)[O-])C=CC=CC=CC=C4C(C5=C(N4CCCCS(=O)(=O)[O-])C=CC6=CC=CC=C65)(C)C)C.[Na+]
• Recent ClinicalTrials: IGG Using in Laparoscopic Gastrectomy for Locally Advanced Gastric Cancer After Neoadjuvant Chemotherapy
• Recent EU Clinical Trials: Selective Indocyanine Green Injection of a Segmental Hepatic Artery Followed by Near-Infrared Fluorescence
• Recent NIPH Clinical Trials: Evaluation of Lymphatic flow using indocyanine green fluorescence imaging
• Uses: A tricarbocyanine type of dye with infrared absorbing properties. Diagnostic aid (blood volume determination, cardiac output, hepatic function). In infrared photography; in preparation of Wratten filters. A tricarbocyanine type of dye with infrared absorbing properties. Diagnostic aid (blood volume determination, cardiac output, hepatic function). Dyes and metabolites.

Technology Process of Sodium 2-(7-(3,3-dimethyl-1-(4-sulfonatobutyl)benz(e)indolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-1-(4-sulfonatobutyl)benz[e]indolinium

There total 10 articles about Sodium 2-(7-(3,3-dimethyl-1-(4-sulfonatobutyl)benz(e)indolin-2-ylidene)hepta-1,3,5-trien-1-yl)-3,3-dimethyl-1-(4-sulfonatobutyl)benz[e]indolinium 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: 85.9%

indocyanine green (28782-33-4) → cardiogreen (3599-32-4)

Guidance literature:

With sodium acetate; In ethanol; at 20 ℃; for 0.5h; Inert atmosphere;

Reference yield: 80.0%

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate (63149-24-6) + glutacondianil hydrochloride (1497-49-0) → cardiogreen (3599-32-4)

Guidance literature:

With sodium acetate; acetic anhydride; In ethanol; at 75 ℃; for 3h; Inert atmosphere; Darkness;

DOI:10.1002/chem.202102816

Reference yield: 42.0%

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate (63149-24-6) + 4-(1,1-dimethyl-2-((1E,3E,5E)-6-(N-phenylacetamido)hexa-1,3,5-trienyl)-1H-benzo[e]indolium-3-yl)butane-1-sulfonate (1351043-94-1,63450-66-8) → indocyanine green (3599-32-4)

Guidance literature:

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate; 4-(1,1-dimethyl-2-((1E,3E,5E)-6-(N-phenylacetamido)hexa-1,3,5-trienyl)-1H-benzo[e]indolium-3-yl)butane-1-sulfonate; With triethylamine; In methanol; at 60 - 65 ℃; for 1.5h;

With sodium iodide; In methanol; at 10 - 65 ℃; for 1.5h;

upstream raw materials:

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate

2,3,3-trimethylbenzo[e]indole

indocyanine green

glutacondianil hydrochloride

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF SODIUM 4-(2-((1E,3E,5E,7Z)-7-(1,1-DIMETHYL-3-(4-SULFONATOBUTYL)-1H-BENZO[e]INDOL-2(3H)-YLIDENE) HEPTA-1,3,5-TRIENYL)-1,1-DIMETHYL-1H-BENZO[e]INDOLIUM-3-YL) BUTANE-1-SULFONATE (INDOCYANINE GREEN)". . . Retrieved 2019/11/19.
• 2、 -. "Method for the purification of betaines". Page/Page column 1-2. . Retrieved 2009/04/24.