Bismark Brown R

• CAT Number: I023436
• CAS Number: 8005-78-5
• Molecular Formula: C21H26Cl2N8
• Molecular Weight: 461.395
• Purity: 98%
• Synonyms: Bismark Brown R; Basic Brown 4; C.I. 21010; C.I. Basic Brown 4
• Solubility: To be determined
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 4,4'-((1E,1'E)-(4-methyl-1,3-phenylene)bis(diazene-2,1-diyl))bis(5-amino-2-methylbenzenaminium) chloride
• InChI: InChI=1S/C21H24N8.2ClH/c1-11-4-5-14(26-28-20-6-12(2)15(22)9-17(20)24)8-19(11)27-29-21-7-13(3)16(23)10-18(21)25;;/h4-10H,22-25H2,1-3H3;2*1H/b28-26+,29-27+
• InChIKey: WLKAMFOFXYCYDK-CYXDXXRZSA-N
• SMILES: Cc1c([NH3+])cc(N)c(/N=N/c2cc(/N=N/c3c(N)cc([NH3+])c(C)c3)c(C)cc2)c1.[Cl-].[Cl-]

Bismark brown R is a brown dye used in leather. In microscopy it is used for staining.

Reference

1: Enayatzamir K, Tabandeh F, Yakhchali B, Alikhani HA, Rodríguez Couto S. Assessment of the joint effect of laccase and cellobiose dehydrogenase on the decolouration of different synthetic dyes. J Hazard Mater. 2009 Sep 30;169(1-3):176-81. doi: 10.1016/j.jhazmat.2009.03.088. Epub 2009 Mar 27. PMID: 19376643.
2: Enayatzamir K, Alikhani HA, Yakhchali B, Tabandeh F, Rodríguez-Couto S. Decolouration of azo dyes by Phanerochaete chrysosporium immobilised into alginate beads. Environ Sci Pollut Res Int. 2010 Jan;17(1):145-53. doi: 10.1007/s11356-009-0109-5. Epub 2009 Mar 4. PMID: 19259719.
3: Boschnakow A, Treudler R, Lieps D, Steinhoff M, Orfanos CE. Temporäre Tätowierung mit Henna induziert Kontaktallergie auf Textilfarbstoffe [Temporary tattooing with henna induces contact allergy to textile dyes]. J Dtsch Dermatol Ges. 2003 Dec;1(12):962-4. German. PMID: 16285649.
4: Bhatnagar A, Jain AK. A comparative adsorption study with different industrial wastes as adsorbents for the removal of cationic dyes from water. J Colloid Interface Sci. 2005 Jan 1;281(1):49-55. doi: 10.1016/j.jcis.2004.08.076. PMID: 15567379.
5: Garde JJ, Ortiz N, García A, Gallego L. Use of a triple-stain technique to detect viability and acrosome reaction in deer spermatozoa. Arch Androl. 1997 Jul-Aug;39(1):1-9. doi: 10.3109/01485019708987895. PMID: 9202827.
6: Choi JK, Yoon SH, Hong HY, Choi DK, Yoo GS. A modified Coomassie blue staining of proteins in polyacrylamide gels with Bismark brown R. Anal Biochem. 1996 Apr 5;236(1):82-4. doi: 10.1006/abio.1996.0134. PMID: 8619499.
7: Sole GM, Chipman JK. The mutagenic potency of chrysoidines and bismark brown dyes. Carcinogenesis. 1986 Nov;7(11):1921-3. doi: 10.1093/carcin/7.11.1921. PMID: 3769140.