2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide

Base Information

• Chemical Name: 2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide
• CAS No.: 119569-97-0
• Molecular Formula: C₂₇H₃₀ClN₂*I
• Molecular Weight: 544.906
• DSSTox Substance ID: DTXSID90694755
• Mol file: 119569-97-0.mol

Synonyms:119569-97-0;2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide;2-[3-chloro-5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]-1,3,3-trimethylindole;iodide;2-[(1E,3Z)-3-CHLORO-5-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)-1,3-PENTADIENYL]-1,3,3-TRIMET;DTXSID90694755

Chemical Property of 2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide

Chemical Property:

• PSA: 6.25000
• LogP: 3.71080
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 544.11422
• Heavy Atom Count: 31
• Complexity: 735

Purity/Quality:

99% ^*data from raw suppliers

2-((1E,3Z)-3-CHLORO-5-(1,3,3-TRIMETHYL-1,3-DIHYDRO-2H-INDOL-2-YLIDENE)-1,3-PENTADIENYL)-1,3,3-TRIMETHYL-3H-INDOLIUM IODIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2[N+](=C1C=CC(=CC=C3C(C4=CC=CC=C4N3C)(C)C)Cl)C)C.[I-]

Technology Process of 2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide

There total 7 articles about 2-[3-Chloro-5-(1,3,3-trimethyl-1,3-dihydro-2H-indol-2-ylidene)penta-1,3-dien-1-yl]-1,3,3-trimethyl-3H-indol-1-ium iodide 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: 64.0%

(E)-N-((Z)-2-chloro-3-(phenylamino)allylidene)benzenaminium chloride (1415118-56-7,55526-63-1) + 1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) → 2-((1E,3Z,5E)-3-chloro-5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide (119569-97-0)

Guidance literature:

With sodium acetate; acetic anhydride; at 40 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00475

Reference yield: 64.0%

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) + N-[2-chloro-3-(phenylamino)-2-propenylidene]-benzenamine monohydrochloride (6684-16-8,55526-63-1) → 2-((1E,3Z,5E)-3-chloro-5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide (119569-97-0)

Guidance literature:

With sodium acetate; acetic anhydride; at 40 - 60 ℃; for 2h;

DOI:10.1021/acs.jmedchem.6b00038

Reference yield:

aniline (62-53-3) → 2-((1E,3Z,5E)-3-chloro-5-(1,3,3-trimethylindolin-2-ylidene)penta-1,3-dien-1-yl)-1,3,3-trimethyl-3H-indol-1-ium iodide (119569-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol

2: sodium acetate; acetic anhydride / 40 °C / Inert atmosphere

With sodium acetate; acetic anhydride; In ethanol;

DOI:10.1021/acs.jmedchem.5b00475

upstream raw materials:

1,2,3,3-tetramethyl-3H-indolium iodide

N-[2-chloro-3-(phenylamino)-2-propenylidene]-benzenamine monohydrochloride

2,3,3-trimethylindoleniune

(E)-N-((Z)-2-chloro-3-(phenylamino)allylidene)benzenaminium chloride

Refernces

• 1、 Owens, Eric A.,Hyun, Hoon,Dost, Tyler L.,Lee, Jeong Heon,Park, Gwangli,Pham, Dang Huan,Park, Min Ho,Choi, Hak Soo,Henary, Maged. "Near-Infrared Illumination of Native Tissues for Image-Guided Surgery". . p. 5311 - 5323. Retrieved 2016/07/06.
• 2、 Owens, Eric A.,Hyun, Hoon,Tawney, Joseph G.,Choi, Hak Soo,Henary, Maged. "Correlating molecular character of NIR imaging agents with tissue-specific uptake". . p. 4348 - 4356. Retrieved 2015/06/08.