Bisbenzimide

Names
Preferred IUPAC name

2′-(4-Ethoxyphenyl)-6-(4-methylpiperazin-1-yl)-1H,3′H-2,5′-bi-1,3-benzimidazole

Other names

Hoechst 33342; Hoe 33342

Identifiers

CAS Number

* 23491-52-3 Y
* 23491-45-4 (trihydrochloride) Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 1420

PubChem CID

* 1464

UNII |

* 99KZS6CNZX Y
* MHT095273M (trihydrochloride) Y

InChI

* InChI=1S/C27H28N6O/c1-3-34-21-8-4-18(5-9-21)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-7-20(17-25(23)31-27)33-14-12-32(2)13-15-33/h4-11,16-17H,3,12-15H2,1-2H3,(H,28,30)(H,29,31)

Key: PRDFBSVERLRRMY-UHFFFAOYSA-N

* InChI=1/C27H28N6O/c1-3-34-21-8-4-18(5-9-21)26-28-22-10-6-19(16-24(22)30-26)27-29-23-11-7-20(17-25(23)31-27)33-14-12-32(2)13-15-33/h4-11,16-17H,3,12-15H2,1-2H3,(H,28,30)(H,29,31)

Key: PRDFBSVERLRRMY-UHFFFAOYAR

SMILES

* CCOc1ccc(cc1)c2[nH]c3cc(ccc3n2)c4[nH]c5cc(ccc5n4)N6CCN(CC6)C

Properties

Chemical formula

| C27H28N6O
Molar mass | 452.562 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Bisbenzimide (Hoechst 33342) is an organic compound used as a fluorescent stain for DNA in molecular biology applications.[1] Several related chemical compounds are used for similar purposes and are collectively called Hoechst stains.

## Application

Bisbenzimide tends to bind to adenine–thymine-rich regions of DNA and can decrease its density. Bisbenzimide mixed with DNA samples can then be used to separate DNA according to their AT percentage using a cesium chloride (CsCl) gradient centrifugation.

Nuclei of Platynereis dumerilii larvae stained with Hoechst 33342

## References

1. ↑ "bisBenzimide H 33342 trihydrochloride". Sigma-Aldrich. https://www.sigmaaldrich.com/catalog/product/sigma/14533.

## External links

* Fluorescence Spectra: http://www.fluorophores.tugraz.at/substance/463

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*[CID]: Compound ID