207399-07-3

Basic information

• Product Name: 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE
• Synonyms: IR-780 IODIDE;2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE;2-[2-[2-CHLORO-3-[2-(1,3-DIHYDRO-1-(PROP-1-YL)-3,3-TRIMETHYL-2H-INDOL-2-YLIDENE)-ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-1-(PROP-1-YL)-3,3-TRIMETHYL-3H-INDOLIUM IODIDE;2-(2-(2-Chloro-3-(2-(1,3-dihydro-1-(prop-1-yl)-3,3-trimethyl-2H-indol-2-ylidene)ethylidene)-1-cyclohexen-1-yl)ethenyl)-;11-CHLORO-1,1''-DIPROPYL-3,3,3'',3''-TETRAMETHYL-10,12-TRIMETHYLENEINDATRICARBOCYANINE IODIDE;IR-780 iodide,2-[2-[2-Chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide;11-Chloro-1,1'-di-n-propyl-3,3,3',3'-tetraMethyl-10,12-triMethyleneindatricarbocyanine iodide;2-(2-(2-Chloro-3-(-2-(3,3-dimethyl-1-propylindolin-2-ylidene)ethylidene)cyclohex-1-enyl)vinyl)-3,3-dimethyl-1-propyl-3H-indolium iodide
• CAS NO: 207399-07-3
• Molecular Formula: C36H44ClIN2
• Molecular Weight: 667.11
• Mol File: 207399-07-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 232-234 °C(lit.)
• Appearance: solid
• Solubility: It is soluble in methanol.
• CAS DataBase Reference: 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE(207399-07-3)
• EPA Substance Registry System: 2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE(207399-07-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 22-24/25-60-37-26-23
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 207399-07-3(Hazardous Substances Data)

Usage

Description

2-[2-[2-CHLORO-3-[(1,3-DIHYDRO-3,3-DIMETHYL-1-PROPYL-2H-INDOL-2-YLIDENE)ETHYLIDENE]-1-CYCLOHEXEN-1-YL]ETHENYL]-3,3-DIMETHYL-1-PROPYLINDOLIUM IODIDE, also known as IR-780 iodide, is a near-infrared lipophilic cation heptamethine fluorescent dye. It possesses good fluorescent intensity and exhibits an optical absorption spectrum of 780 nm, making it a promising candidate for various applications in the medical and industrial fields.

Uses

Used in Medical Applications:
IR-780 iodide is used as a photothermal therapy agent for the treatment of various medical conditions. Its near-infrared absorption properties allow for effective targeting and treatment of diseases at the cellular level.
Used in Diagnostic Imaging:
Due to its strong fluorescence, IR-780 iodide is employed as a contrast agent in diagnostic imaging techniques, such as fluorescence imaging and near-infrared imaging, to enhance the visualization of specific tissues or organs.
Used in Laser and IR Dye Applications:
IR-780 iodide is utilized as a laser and IR dye in various industrial applications, including lithographic computer-to-plate laser applications, where its near-infrared absorption properties provide enhanced performance and efficiency.
Used in Sonodynamic Therapy:
The optical absorption spectrum of 780 nm makes IR-780 iodide a suitable agent for sonodynamic therapy, a medical treatment that combines the use of ultrasound and a photosensitizer to generate reactive oxygen species, leading to the destruction of targeted cells.
Used in Pharmaceutical Research:
The unique properties of IR-780 iodide make it a valuable compound in pharmaceutical research, where it can be explored for potential applications in drug delivery systems, targeting specific biological processes, and developing novel therapeutic strategies.

InChI:InChI=1/C36H44ClN2.HI/c1-7-24-38-30-18-11-9-16-28(30)35(3,4)32(38)22-20-26-14-13-15-27(34(26)37)21-23-33-36(5,6)29-17-10-12-19-31(29)39(33)25-8-2;/h9-12,16-23H,7-8,13-15,24-25H2,1-6H3;1H/q+1;/p-1

Synthetic route

2-chloro-1-formyl-3-hydroxymethylenecyclohexene (61010-04-6) + 2,3,3-trimethyl-1-propyl-3H-indolium iodide (20205-29-2) → 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3)

Conditions	Yield
In butan-1-ol; benzene at 160℃; for 10h; Inert atmosphere;	96%
In butan-1-ol; benzene at 160℃; for 10h; Inert atmosphere;	96%
In butan-1-ol; benzene at 160℃; for 10h; Inert atmosphere; Dean-Stark;	96%

2,3,3-trimethyl-1-propyl-3H-indolium iodide (20205-29-2) + N-((2-chloro-3-((phenylimino)methyl)cyclohex-2-en-1-ylidene)methyl)aniline → 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3)

Conditions	Yield
With sodium acetate In ethanol at 50℃; for 1h;	79%

2,3,3-trimethylindoleniune (1640-39-7) → 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile / 15 h / Reflux 2: butan-1-ol; benzene / 10 h / 160 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: acetonitrile / 15 h / Reflux 2: butan-1-ol; benzene / 10 h / 160 °C / Inert atmosphere; Dean-Stark View Scheme
Multi-step reaction with 2 steps 1: 5 h / Reflux 2: sodium acetate / ethanol / 1 h / 50 °C View Scheme

cyclohexanone (108-94-1) → 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / dichloromethane / 0.5 h / Inert atmosphere; cooling with ice 1.2: 3 h / 80 °C 2.1: butan-1-ol; benzene / 10 h / 160 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: trichlorophosphate / dichloromethane / 3 h / 80 °C / Inert atmosphere 2: butan-1-ol; benzene / 10 h / 160 °C / Inert atmosphere; Dean-Stark View Scheme
Multi-step reaction with 2 steps 1.1: trichlorophosphate / dichloromethane / 0.17 h / 0 °C 1.2: 3.2 h / Reflux 1.3: 1 h / 20 °C 2.1: sodium acetate / ethanol / 1 h / 50 °C View Scheme

2,3,3-trimethyl-1-propyl-3H-indolium iodide (20205-29-2) + N-((E)-(2-chloro-3-((E)-(phenylimino)methyl)cyclohex-2-enylidene)methyl)aniline → 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3)

Conditions	Yield
With sodium acetate In ethanol at 120℃; for 0.333333h; Microwave irradiation;

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + tert-butyl (4-hydroxybenzyl)carbamate (149505-94-2) → 2-(2-{2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene]-2-(4-tert-butylcarbamate aminomethylphenoxy)-1-cyclohexen-1-yl}ethenyl)-3,3-dimethyl-1-propylindolium iodide

Conditions	Yield
With caesium carbonate In dichloromethane at 40℃; for 1h; Inert atmosphere;	100%
With caesium carbonate In dichloromethane at 40℃; for 1h; Inert atmosphere;	100%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + phosphomolybdic acid triacontahydrate → Mo12O40P(3-)*3C36H44ClN2(1+)

Conditions	Yield
In ethanol; water	96%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + phosphotungstic acid triacontahydrate + phosphomolybdic acid triacontahydrate → 0.5Mo12O40P(3-)*3C36H44ClN2(1+)*0.5O40PW12(3-)

Conditions	Yield
In ethanol; water	94%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + phosphotungstic acid triacontahydrate → 3C36H44ClN2(1+)*O40PW12(3-)

Conditions	Yield
In ethanol; water	93%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + 4-mercaptobenzoic acid (1074-36-8) → C43H49N2O2S(1+)*I(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere;	92%
In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	85%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + phosphotungstic acid triacontahydrate + phosphomolybdic acid triacontahydrate → 0.3Mo12O40P(3-)*3C36H44ClN2(1+)*0.7O40PW12(3-)

Conditions	Yield
In ethanol; water	92%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + 2-(4'-hydroxyphenyl)-1,2-benzoisoselenazol-3(2H)-one (81744-01-6) → C49H52N3O2Se(1+)*I(1-)

Conditions

Yield

Stage #1: 2-(4'-hydroxyphenyl)-1,2-benzoisoselenazol-3(2H)-one With potassium tert-butylate In tetrahydrofuran at 15℃; for 0.5h; Inert atmosphere; Stage #2: 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide In tetrahydrofuran at 60℃; for 5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

92%

piperazine (110-85-0) + 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) → C40H53N4(1+)*I(1-) (1477522-55-6)

Conditions	Yield
In acetonitrile at 82℃; for 4h; Inert atmosphere;	90%
In N,N-dimethyl-formamide at 85℃; for 4h;	86%
In N,N-dimethyl-formamide at 85℃; for 4h; Inert atmosphere;	85%

piperazine (110-85-0) + 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) → C40H53N4(1+) (1477612-49-9)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 4h;	87.4%
In N,N-dimethyl-formamide at 85℃; for 4h; Inert atmosphere;

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + ethylamine (75-04-7) → C38H50N3(1+)*I(1-) (1255954-15-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.333333h;	87%
With triethylamine In acetonitrile at 80℃;

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + thiophenol (108-98-5) → IR-792

Conditions	Yield
In N,N-dimethyl-formamide at 25℃; for 10h; Inert atmosphere; Schlenk technique;	87%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + aluminium(III) sulfate hexahydrate → 3C38H46ClN2O6S2(1-)*Al(3+)

Conditions	Yield
With sodium hydroxide In water	87%

2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) + 4-Chlororesorcinol (95-88-5) → C28H29ClNO2(1+)

Conditions	Yield
Stage #1: 4-Chlororesorcinol With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide In N,N-dimethyl-formamide at 75℃; for 6h; Inert atmosphere;	86.9%

2-(aminoethyl)pyridine (2706-56-1) + 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indolyl-2-ylidenyl)ethylidenyl]-1-cyclohexen-1-yl]ethenyl]-3,3-dimethyl-1-propylindolium iodide (207399-07-3) → C43H53N4(1+)*I(1-)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.333333h;	85%

Upstream product

• 61010-04-6 2-chloro-1-formyl-3-hydroxymethylenecyclohexene 
• 20205-29-2 2,3,3-trimethyl-1-propyl-3H-indolium iodide 
• 1640-39-7 2,3,3-trimethylindoleniune 
• 108-94-1 cyclohexanone 

Downstream Products

• 1380599-31-4 C₄₂H₅₀N₃⁽¹⁺⁾*I^(1-) 
• 1262963-05-2 C₅₈H₇₉N₄O₄⁽¹⁺⁾*I^(1-) 
• 1262963-06-3 C₆₀H₈₃N₄O₈⁽¹⁺⁾*I^(1-) 
• 1262963-01-8 C₅₆H₇₅N₄O₆⁽¹⁺⁾*I^(1-) 
• 1262963-07-4 C₄₉H₆₂N₃O₃⁽¹⁺⁾*I^(1-) 
• 1242439-55-9 C₄₇H₅₈N₃O₃⁽¹⁺⁾*I^(1-) 
• 1428582-92-6 C₄₂H₄₇F₂N₂⁽¹⁺⁾*I^(1-) 

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