3599-32-4

Basic information

• Product 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
• Synonyms: 4-(2-{7-[1,1-Dimethyl-3-(4-sulfo-butyl)-1H-benzo[e]indol-2-yl]-hepta-2,4,6-trienylidene}-1,1-dimethyl-benzo[e]indolium-3-yl)-butane-1-sulfonic acid sodium salt;IR-125,pure,laser grade;Cardiogreen,Foxgreen, IC Green, Indocyanine green;Indocyanine Green (~90%);Indocyanine Green (250 mg);4-(2-{7-[1,1-Dimethyl-3-(4-sulfo-butyl)-1H-benzo[e]indol-2-yl]-hepta-2,4,6-trienylidene}-1,1-dimethyl-benzo[e]indolium-3-yl)-butane-1-sulfonic acid sodium;sodiuM 2-[(1E,3E,5E)-7-[(2Z)-1,1-diMethyl-3-(4-sulfonatobutyl)-1H,2H,3H-benzo[e]indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-diMethyl-1-(4-sulfonatobutyl)-3H-benzo[f]indol-1-iuM;IR-125, laser grade, pure 100MG
• CAS NO: 3599-32-4
• Molecular Formula: C₄₃H₄₇N₂O₆S₂*Na
• Molecular Weight: 774.96
• EINECS: 222-751-5
• Product Categories: Cyanine Dyes;Fluorescent Labels & Indicators;Sulfur & Selenium Compounds
• Mol File: 3599-32-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 235 °C
• Boiling Point: 157oC
• Appearance: Green-bronze/Powder
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: H2O: soluble1mg/mL
• Water Solubility: slightly soluble
• Merck: 14,4962
• BRN: 4115884
• CAS DataBase Reference: 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 DataBase Reference)
• NIST Chemistry Reference: 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(3599-32-4)
• EPA Substance Registry System: 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(3599-32-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: DE3150000
• Hazardous Substances Data: 3599-32-4(Hazardous Substances Data)

Usage

Chemical Properties

green to brown crystals or crystalline powder

Uses

Different sources of media describe the Uses of 3599-32-4 differently. You can refer to the following data:
1. A tricarbocyanine type of dye with infrared absorbing properties. Diagnostic aid (blood volume determination, cardiac output, hepatic function).
2. In infrared photography; in preparation of Wratten filters.
3. A tricarbocyanine type of dye with infrared absorbing properties. Diagnostic aid (blood volume determination, cardiac output, hepatic function). Dyes and metabolites.

Brand name

IC-Green (Akorn).

Safety Profile

Poison by intravenous route. When heated to decomposition it emits very toxic fumes of SOx, Na2O, and NOx.

InChI:InChI=1/C43H48N2O6S2.Na/c1-42(2)36-26-24-32-18-10-12-20-34(32)40(36)44(28-14-16-30-52(46,47)48)38(42)22-8-6-5-7-9-23-39-43(3,4)37-27-25-33-19-11-13-21-35(33)41(37)45(39)29-15-17-31-53(49,50)51;/h5-13,18-27H,14-17,28-31H2,1-4H3,(H-,46,47,48,49,50,51);/q;+1/p-1/rC43H47N2NaO6S2/c1-42(2)36-26-24-32-18-10-12-20-34(32)40(36)44(28-14-16-30-53(47,48)49)38(42)22-8-6-5-7-9-23-39-43(3,4)37-27-25-33-19-11-13-21-35(33)41(37)45(39)29-15-17-31-54(50,51)52-46/h5-13,18-27H,14-17,28-31H2,1-4H3

Synthetic route

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)

Conditions	Yield
Stage #1: 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; Stage #2: With sodium iodide In methanol at 10 - 65℃; for 1.5h;	42%

4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate (63149-24-6) + (E)-N-((2E,4E)-5-(phenylamino)penta-2,4-dienylidene)aniline hydrochloride → indocyanine green (3599-32-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1.5 h / 130 - 140 °C 2.1: triethylamine / methanol / 1.5 h / 60 - 65 °C 2.2: 1.5 h / 10 - 65 °C View Scheme

1-(2,4-dinitrophenyl)-pyridinium chloride (4185-69-7) → indocyanine green (3599-32-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanol / water / 2 h / 25 - 30 °C 2.1: 1.5 h / 130 - 140 °C 3.1: triethylamine / methanol / 1.5 h / 60 - 65 °C 3.2: 1.5 h / 10 - 65 °C View Scheme

2,3,3-trimethylbenzo[e]indole (41532-84-7) → indocyanine green (3599-32-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 18 h / 140 - 150 °C 2.1: 1.5 h / 130 - 140 °C 3.1: triethylamine / methanol / 1.5 h / 60 - 65 °C 3.2: 1.5 h / 10 - 65 °C View Scheme

pyridine (110-86-1) → indocyanine green (3599-32-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: acetone / 12 - 14 h / 60 - 65 °C 2.1: methanol / water / 2 h / 25 - 30 °C 3.1: 1.5 h / 130 - 140 °C 4.1: triethylamine / methanol / 1.5 h / 60 - 65 °C 4.2: 1.5 h / 10 - 65 °C View Scheme

Upstream product

• 110-86-1 pyridine 
• 41532-84-7 2,3,3-trimethylbenzo[e]indole 
• 4185-69-7 1-(2,4-dinitrophenyl)-pyridinium chloride 
• 63149-24-6 4-(1,1,2-trimethyl-1H-benzo[e]indol-3-ium-3-yl)butane-1-sulfonate 
• 1351043-94-1 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 
• 1497-49-0 glutacondianil hydrochloride 
• 28782-33-4 indocyanine green 

Relevant articles and documents

Deuterated Indocyanine Green (ICG) with Extended Aqueous Storage Shelf-Life: Chemical and Clinical Implications

Indocyanine Green (ICG) is a clinically approved near-infrared fluorescent dye that is used extensively for various imaging and diagnostic procedures. One drawback with ICG is its instability in water, which means that reconstituted clinical doses have to be used very shortly after preparation. Two deuterated versions of ICG were prepared with deuterium atoms on the heptamethine chain, and the spectral, physiochemical, and photostability properties were quantified. A notable mechanistic finding is that self-aggregation of ICG in water strongly favors dye degradation by a photochemical oxidative dimerization reaction that gives a nonfluorescent product. Storage stability studies showed that replacement of C?H with C?D decreased the dimerization rate constant by a factor of 3.1, and it is likely that many medical and preclinical procedures will benefit from the longer shelf-lives of these two deuterated ICG dyes. The discovery that ICG self-aggregation promotes photoinduced electron transfer can be exploited as a new paradigm for next-generation photodynamic therapies.

Indocyanine green, and preparation method and application thereof

The invention provides indocyanine green, and a preparation method and application thereof. The indocyanine green is shown as formula 1. The method is performed according to a path recorded in the specification. According to the path, 2, 3, 3-trimethyl-4, 5-benzoindoles, 1, 4-butyl sultone and 2-glutarate diphenylamine hydrochloride, as raw materials, are compounded into the indocyanine green shown as the target compound formula 1. The method has a short compounding path, simple process and high yield, does not need heavy metal catalysis, and meets requirements of 'green chemical' development.