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3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole (CAS 27933-36-4)

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Alternate Names:
BNPS skatole
Application:
CAS Number:
27933-36-4
Purity:
≥85%
Molecular Weight:
363.23
Molecular Formula:
C15H11BrN2O2S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole is a peptide cleavage reagent specific for the carboxyl side of tryptophan residues. 3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole is a synthesized compound originating from skatole, an aromatic compound present in animal feces and tobacco. It has been the subject of investigation as a prospective insect repellent, primarily due to its demonstrated insecticidal properties in laboratory experiments.


3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole (CAS 27933-36-4) References

  1. Photoaffinity labeling of the nucleotide-binding site of the uncoupling protein from hamster brown adipose tissue.  |  Winkler, E. and Klingenberg, M. 1992. Eur J Biochem. 203: 295-304. PMID: 1730236
  2. Mapping general anesthetic binding site(s) in human α1β3 γ-aminobutyric acid type A receptors with [³H]TDBzl-etomidate, a photoreactive etomidate analogue.  |  Chiara, DC., et al. 2012. Biochemistry. 51: 836-47. PMID: 22243422
  3. [34] Modification of tryptophan with BNPS-skatole (2-(2-nitrophenylsulfenyl)-3-methyl-3-bromoindolenine).  |  Fontana, A. 1972. Methods Enzymol. 25: 419-23. PMID: 23014422
  4. Mink serum amyloid A protein. Expression and primary structure based on cDNA sequences.  |  Marhaug, G., et al. 1990. J Biol Chem. 265: 10049-54. PMID: 2351648
  5. Photoaffinity labeling the propofol binding site in GLIC.  |  Chiara, DC., et al. 2014. Biochemistry. 53: 135-42. PMID: 24341978
  6. Pronase E-Based Generation of Fluorescent Peptide Fragments: Tracking Intracellular Peptide Fate in Single Cells.  |  Mainz, ER., et al. 2015. Anal Chem. 87: 7987-95. PMID: 26171808
  7. Identification, Characterization, and Three-Dimensional Structure of the Novel Circular Bacteriocin, Enterocin NKR-5-3B, from Enterococcus faecium.  |  Himeno, K., et al. 2015. Biochemistry. 54: 4863-76. PMID: 26174911
  8. Positive and Negative Allosteric Modulation of an α1β3γ2 γ-Aminobutyric Acid Type A (GABAA) Receptor by Binding to a Site in the Transmembrane Domain at the γ+-β- Interface.  |  Jayakar, SS., et al. 2015. J Biol Chem. 290: 23432-46. PMID: 26229099
  9. In Silico Proteome Cleavage Reveals Iterative Digestion Strategy for High Sequence Coverage.  |  Meyer, JG. 2014. ISRN Comput Biol. 2014: PMID: 30687733
  10. Feasability of Introducing a Thioether Ring in Vasopressin by nisBTC Co-expression in Lactococcus lactis.  |  Li, Q., et al. 2019. Front Microbiol. 10: 1508. PMID: 31333616
  11. Purification, Characterization, Identification, and Anticancer Activity of a Circular Bacteriocin From Enterococcus thailandicus.  |  Al-Madboly, LA., et al. 2020. Front Bioeng Biotechnol. 8: 450. PMID: 32656185
  12. Poly(ADP-ribose) polymerase from Ehrlich ascites-tumour cells. Amino acid composition, N-terminal analysis and chemical cleavage of the purified protein.  |  Holtlund, J., et al. 1980. Biochem J. 185: 779-82. PMID: 6248036
  13. Peptide fragmentation suitable for solid-phase microsequencing. Use of N-bromosuccinimide and BNPS-skatole (3-bromo-3-methyl-2-[(2-nitrophenyl)thio]-3H-indole).  |  Hunziker, PE., et al. 1980. Biochem J. 187: 515-9. PMID: 7396860

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

3-Bromo-3-methyl-2-(2-nitrophenylthio)-3H-indole, 100 mg

sc-254434
100 mg
$163.00