1,3-diethyl-2-[(E,3E)-3-(1,3,3-trimethylindol-2-ylidene)prop-1-enyl]-1,2-dihydrobenzo[f]benzimidazol-1-ium;chloride

Base Information

• Chemical Name: 1,3-diethyl-2-[(E,3E)-3-(1,3,3-trimethylindol-2-ylidene)prop-1-enyl]-1,2-dihydrobenzo[f]benzimidazol-1-ium;chloride
• CAS No.: 139167-47-8
• Molecular Formula: C₂₉H₃₂N₃*Cl
• Molecular Weight: 458.046
• Mol file: 139167-47-8.mol

Synonyms:1,3-diethyl-2-(3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl)-1H-naphth(2,3-d)imidazolium;TYP-NIC

Chemical Property of 1,3-diethyl-2-[(E,3E)-3-(1,3,3-trimethylindol-2-ylidene)prop-1-enyl]-1,2-dihydrobenzo[f]benzimidazol-1-ium;chloride

Chemical Property:

• Vapor Pressure: 1.72E-13mmHg at 25°C
• Boiling Point: 581°Cat760mmHg
• Flash Point: 315.2°C
• PSA: 10.92000
• Density: g/cm³
• LogP: 7.09800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 459.2441258
• Heavy Atom Count: 33
• Complexity: 724

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[NH+]1C(N(C2=CC3=CC=CC=C3C=C21)CC)C=CC=C4C(C5=CC=CC=C5N4C)(C)C.[Cl-]
• Isomeric SMILES: CC[NH+]1C(N(C2=CC3=CC=CC=C3C=C21)CC)/C=C/C=C/4\C(C5=CC=CC=C5N4C)(C)C.[Cl-]

Technology Process of 1,3-diethyl-2-[(E,3E)-3-(1,3,3-trimethylindol-2-ylidene)prop-1-enyl]-1,2-dihydrobenzo[f]benzimidazol-1-ium;chloride

There total 5 articles about 1,3-diethyl-2-[(E,3E)-3-(1,3,3-trimethylindol-2-ylidene)prop-1-enyl]-1,2-dihydrobenzo[f]benzimidazol-1-ium;chloride 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: 95.6%

1,3-diethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide (139167-43-4) → 1,3-diethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium chloride (139167-47-8)

Guidance literature:

With amberlite IRA-400 chloride ion-exchange resin; for 2h; Ambient temperature;

DOI:10.1021/jm00085a015

Reference yield:

1H-2-methylnaphtho[2,3-d]imidazole (1792-36-5) → 1,3-diethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium chloride (139167-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 53.8 percent / potassium hydroxide / acetone / 3 h / Ambient temperature

2: 94.3 percent / 4 h / 100 °C

3: 85.4 percent / DBU / acetonitrile / 0.5 h / Heating

4: 95.6 percent / amberlite IRA-400 chloride ion-exchange resin / 2 h / Ambient temperature

With potassium hydroxide; amberlite IRA-400 chloride ion-exchange resin; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; acetonitrile;

DOI:10.1021/jm00085a015

Reference yield:

2,3-Diaminonaphthalene (771-97-1) → 1,3-diethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium chloride (139167-47-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 68.7 percent / concd. sulfuric acid / dimethylformamide / a) 120 deg C, 2 h, b) 140 deg C, 2 h

2: 53.8 percent / potassium hydroxide / acetone / 3 h / Ambient temperature

3: 94.3 percent / 4 h / 100 °C

4: 85.4 percent / DBU / acetonitrile / 0.5 h / Heating

5: 95.6 percent / amberlite IRA-400 chloride ion-exchange resin / 2 h / Ambient temperature

With potassium hydroxide; amberlite IRA-400 chloride ion-exchange resin; sulfuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm00085a015

upstream raw materials:

1,3-diethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1-propenyl>-1H-naphth<2,3-d>imidazolium iodide

1H-2-methylnaphtho[2,3-d]imidazole

2,3-Diaminonaphthalene

1-ethyl-2-methyl-1H-naphth<2,3-d>imidazole