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

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

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 
• 108-94-1 cyclohexanone 
• 1640-39-7 2,3,3-trimethylindoleniune 

Downstream Products

• 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-) 
• 1587704-67-3 C₄₆H₅₅N₆O₆S⁽¹⁺⁾*I^(1-) 

Relevant articles and documents

Co-delivery of Cu(I) chelator and chemotherapeutics as a new strategy for tumor theranostic

Chelating Cu from tumors has been verified as an effective and promising strategy for cancer therapy through antiangiogenesis. However, systematic removal Cu by injecting with Cu chelators will result unavoidable side effects, since Cu is indispensable to the body. In this work, a micelle targeting to tumors' newborn vessels based on a polypeptide was developed to co-load DOX and Probe X, which can go through an “OFF-to-ON” procedure to report the Cu+-capture events in vivo in a real-time way by giving near infrared (NIR) fluorescence and photoacoustic signal. By co-delivering antiangiogenesis and chemotherapeutic reagents, the tumor can be significantly suppressed, meanwhile with a low systematic toxicity. Hopefully, this work can offer new insights in designing sophisticated antitumor strategy.

A near-infrared cyanine dye preparation method (by machine translation)

The invention discloses a having excellent light stability of the near-infrared cyanine dye preparation method and use, the dye of the formula I as shown in the structural formula, R1 Hydrogen, methyl, in any one of a carboxyl group; R2 Hydrogen, methyl, alkoxy in any one of; X- Is iodine ion, bromide ion in any one of; n=1 - 5 is any integer. The dye through chemical bonding will be blocked piperidine structure unit introduced into the cycloheptane boeki indole cyanine in the mother's body, such that the resulting dye has good light stability, in the near-infrared region with absorption and emission, and has good photosensitive, photo-thermal characteristic, so that the fabric is colored, near-infrared fluorescence imaging, the photodynamic treatment, heat treating the field have good application prospect. (by machine translation)

A cyanine-based fluorescent cassette with aggregation-induced emission for sensitive detection of pH changes in live cells

An aggregation-induced emission (AIE) cyanine-based fluorescent cassette with a large pseudo-Stokes shift was designed and prepared to sensitively image pH changes in live cells via through-bond energy transfer (TBET) from a tetraphenylethene (TPE) donor to a cyanine acceptor.

Probe for early diagnosis of tumor as well as synthesis and application of probe

The invention discloses an NQO (quinone oxidoreductase) response type near infrared fluorescence probe compound related to early diagnosis of tumor. The structure of the compound is represented as theformula (I), wherein R1 and R2 are the same or different, and R1 and R2 are independently selected from C1-6 linear alkyl, C1-6 linear alkyl carboxyl, sulfonyl or C1-6 linear alkyl ester; X is halogen. The primary cell confocal experiment of the compound proves that the compound has good NQO response capacity, can produce strong fluorescence easy to detect, and can be applied to early detection of tumor.

Photophysical properties of near-IR cyanine dyes and their application as photosensitizers in dye sensitized solar cells

The photophysical properties of eight structurally diverse near-infrared cyanine dyes were investigated with respect to their structural features and potential use as light-harvesting sensitizers of dye sensitized solar cells. The absorption, emission, and lifetime characteristics of the dyes were assessed under a variety of conditions. The photophysical properties and sensitizing efficiency of three of the eight dyes, with an additional six-membered cyclic ring, were markedly different from the other five. The dyes absorbed light of wavelength within the range of 779–823 nm and emitted within the range of 832–876 nm.The dyes had fluorescence quantum yield in the range of 14–22%. The surface morphology and elemental analysis of the cyanine dye sensitized photoanodes were characterized via Field-Emission Scanning Microscopy Imaging (FESEM) and Transmission Electron Microscopy (TEM). The performance of the fabricated cyanine dye sensitized solar cells was assessed via current-voltage and electrochemical impedance spectroscopic measurements. The solar-to-electric power conversion efficiency ranged from 0.04% to 0.24%.

Cyanine dye for laveling biomolecule and preparation method thereof

The present invention relates to a cyanine dye represented by [Chemical Formula 1] for labeling a biomolecule and a method for producing the same. [Chemical Formula 1] In [Chemical Formula 1], each of Y, Z, R_1, R_1andprime;, R_2, R_2andprime;, R_3, l and m is the same as defined in the specification.(AA) MarkerCOPYRIGHT KIPO 2015

A macrophage uptaking near-infrared chemical probe CDnir7 for in vivo imaging of inflammation

Visualization of macrophages in live animals has been of great interest for a better understanding of inflammation. We developed a near infrared (NIR) probe CDnir7 that can selectively detect macrophages and visualize inflammation in vivo using the IVIS spectrum, Fluorescence Molecular Tomography (FMT) and Multi-Spectral Optoacoustic Tomography (MSOT). This journal is the Partner Organisations 2014.

DEVELOPMENT OF PHOTOSTABLE NEAR-IR CYANINE DYES FOR IN VIVO IMAGING

A compound of structural formula (I). The values and alternative values are as defined herein. The invention also includes biosensors comprising nanoparticles functionalized with a compound of structural formula (I). Also described is a method for labeling a biomolecule using a compound of structural formula (I) and a method of detecting a target biomolecule using a compound of structural formula (I) or a biosensor of the invention.

Development of photostable near-infrared cyanine dyes

With the emerging interest in optical in vivo imaging, there is an increasing demand of photostable near-infrared (NIR) dyes. Herein we report the rational design of an amine tricarbocyanine structure with improved photostability (CyNA) and its combinatorial derivatization to render CyNA-414 as a NIR-fluorescent dye with stronger emission intensity and higher photostability than the NIR standard IndoCyanine Green (ICG).