2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride

Base Information

• Chemical Name: 2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride
• CAS No.: 23491-52-3
• Molecular Formula: C27H28 N6 O
• Molecular Weight: 452.559
• Hs Code.: 32129000
• European Community (EC) Number: 245-691-1
• Wikipedia: Bisbenzimide
• Mol file: 23491-52-3.mol

Synonyms:4-(5-(4-Methyl-1-piperazinyl)(2,5'-bi-1H-benzimidazol)-2'-yl)phenol, trihydrochloride;Bisbenzimidazole;Bisbenzimidazole Trihydrochloride;Bisbenzimide;Hoe 33258;Hoe-33258;Hoe33258;Hoechst 33258;NSC 322921;NSC-322921;NSC322921;Pibenzimol

Chemical Property of 2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride

Chemical Property:

• Appearance/Colour: Yellow-green powder.
• Melting Point: 268oC
• Boiling Point: 725.9±70.0 °C(Predicted)
• PKA: 10.97±0.10(Predicted)
• PSA: 100.76000
• Density: 1.274±0.06 g/cm3(Predicted)
• LogP: 7.13970
• Storage Temp.: 2-8°C
• Solubility.: H2O: soluble20mg/mL
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 614.194187
• Heavy Atom Count: 40
• Complexity: 664

Purity/Quality:

≥98.0% ^*data from raw suppliers

Hoechst 33342 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,C
• Statements: 22-37/38-36/37/38-20/21/22-37-35
• Safety Statements: 22-36/37-24/25-36-26-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Dyes -> Other Dyes
• Canonical SMILES: CCOC1=CC=C(C=C1)C2=NC3=C(N2)C=C(C=C3)C4=NC5=C(N4)C=C(C=C5)N6CCN(CC6)C.O.O.O.Cl.Cl.Cl
• Uses: Hoechst 33342 is useful for staining DNA, chromosomes and nuclei. May be used for fluorescence microscopy or flow cytometry. Suitable for vital DNA staining of a variety of cell types and as a probe of membrane permeability in mammalian cells. Hoechst 33342 is an A:T-specific DNA minor groove ligand that is a widely used fluorochrome for visualizing cellular DNA. Excitation of the dye occurs around 350 nm with an emission maxima around 461 nm. Hoechst-33342, unlike other Hoechst dyes, is more lipophillic due to an additional ethyl group. The compound has been observed to displace several known DNA intercalators. Adriamycin has been shown to disrupt the DNA dye update. The compound can be used in sorting living cells based on DNA content by FACS, in the visualization of chromatin distribution in living cells, to detect BrdU incorporation into cells, the visualization of fixed cells by microscopy, and to study the initial stages of apoptosis and cell-cycle distribution. In addition to Hoechst-33342''s fluorescent capability, the

Technology Process of 2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride

There total 11 articles about 2'-(4-Ethoxyphenyl)-5-(4-methyl-1-piperazinyl)-2,5'-bi-1H-benzimidazole trihydrochloride 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: 80.0%

4-ethoxybenzaldehyde (10031-82-0) + 2-amino-4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>aniline (23491-49-8) → 2-[2-(4-ethoxyphenyl)benzimidazol-5(6)-yl]-5(6)-(4-methylpiperazin-1-yl)benzimidazole (23491-52-3)

Guidance literature:

With molecular sieve; In nitrobenzene; toluene; at 98 - 100 ℃; for 36h;

DOI:10.1021/jm9602672

Reference yield:

5-chloro-2-nitroaniline (1635-61-6) → 2-[2-(4-ethoxyphenyl)benzimidazol-5(6)-yl]-5(6)-(4-methylpiperazin-1-yl)benzimidazole (23491-52-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / K₂CO₃ / dimethylformamide / 4.5 h / Heating

2: H₂ / 10percent Pd/C / methanol / 1.25 h / Ambient temperature

3: 1.171 g / AcOH / 12 h / 55 °C

4: H₂ / 10percent Pd/C / methanol / 1.25 h / Ambient temperature

5: 80 percent / mol. sieves / nitrobenzene; toluene / 36 h / 98 - 100 °C

With molecular sieve; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; In methanol; nitrobenzene; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9602672

Reference yield:

1-methyl-piperazine (109-01-3) → 2-[2-(4-ethoxyphenyl)benzimidazol-5(6)-yl]-5(6)-(4-methylpiperazin-1-yl)benzimidazole (23491-52-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 60 percent / K₂CO₃ / dimethylformamide / 4.5 h / Heating

2: H₂ / 10percent Pd/C / methanol / 1.25 h / Ambient temperature

3: 1.171 g / AcOH / 12 h / 55 °C

4: H₂ / 10percent Pd/C / methanol / 1.25 h / Ambient temperature

5: 80 percent / mol. sieves / nitrobenzene; toluene / 36 h / 98 - 100 °C

With molecular sieve; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; In methanol; nitrobenzene; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm9602672

upstream raw materials:

4-ethoxybenzaldehyde

2-amino-4-<5'-(4''-methylpiperazin-1''-yl)benzimidazol-2'-yl>aniline

1-methyl-piperazine

5-chloro-2-nitroaniline

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