Benzidine
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| Benzidine | |
|---|---|
| Image:Benzidine structure.svg | |
| IUPAC name | 4,4'-diaminobiphenyl |
| Other names | Benzidine |
| Molecular formula | C12H12N2 |
| Molar mass | 184.25 |
| CAS number | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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Overview
Benzidine is the trivial name for 4,4'-diaminobiphenyl, a carcinogenic aromatic amine which has been used as part of a test for cyanide and also in the synthesis of dyes. It has been linked to bladder cancer and pancreatic cancer.
In common with benzidine some other aromatic amines such as 2-aminonaphthalene have been withdrawn from use in almost all industries because they are so carcinogenic.
In the past a common test for blood used benzidine but this has largely been replaced by tests using phenolphthalein / hydrogen peroxide and luminol. An enzyme in blood causes the benzidine to be oxidized to a polymer which is blue coloured. The test for cyanide uses similar chemistry to give the blue colour.
Benzidine is a known human carcinogen. [1]
Benzidine rearrangement
In a classic rearrangement reaction called the benzidine rearrangement benzidine is formed by reaction of the 1,2-diphenylhydrazine (PhNHNHPh) with acids. One plausible reaction mechanism has both hydrazine nitrogen atoms protonated after which a sigmatropic reaction takes place [2].
External links
References
- ↑ www.cancer.org Link
- ↑ Advanced Organic Chemistry third edition Jerry March ISBN 047185472-7
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
