Date published: 2026-3-19

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2-Cyano-6-hydroxybenzothiazole (CAS 939-69-5)

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Alternate Names:
6-Hydroxy-benzothiazole-2-carbonitrile
CAS Number:
939-69-5
Purity:
≥95%
Molecular Weight:
176.20
Molecular Formula:
C8H4N2OS
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2-Cyano-6-hydroxybenzothiazole, also referred to as 2-CHBT, holds immense significance in the realm of organic synthesis. Throughout scientific research, 2-Cyano-6-hydroxybenzothiazole has been employed in diverse applications. It exhibits catalytic properties, facilitating organic synthesis as a catalyst, and enabling the synthesis of compounds as a reagent and ligand for metal complexes. Moreover, it serves as a fundamental starting material for synthesizing an array of compounds. Additionally, 2-Cyano-6-hydroxybenzothiazole plays a role in the production of dyes, pigments, and other materials. The precise mechanism of action for 2-Cyano-6-hydroxybenzothiazole remains elusive, although there is speculation that the compound may act as an electron donor, facilitating electron transfer between molecules. This potential electron transfer phenomenon could impart a catalytic effect, enabling the synthesis of compounds that would otherwise prove challenging to produce.


2-Cyano-6-hydroxybenzothiazole (CAS 939-69-5) References

  1. Oxyluciferin, a luminescence product of firefly luciferase, is enzymatically regenerated into luciferin.  |  Gomi, K. and Kajiyama, N. 2001. J Biol Chem. 276: 36508-13. PMID: 11457857
  2. Evolution of beetle bioluminescence: the origin of beetle luciferin.  |  Day, JC., et al. 2004. Luminescence. 19: 8-20. PMID: 14981641
  3. Synthesis of an N-acyl sulfamate analog of luciferyl-AMP: a stable and potent inhibitor of firefly luciferase.  |  Branchini, BR., et al. 2005. Bioorg Med Chem Lett. 15: 3860-4. PMID: 15990297
  4. New bioluminogenic substrates for monoamine oxidase assays.  |  Zhou, W., et al. 2006. J Am Chem Soc. 128: 3122-3. PMID: 16522074
  5. Firefly bioluminescence: a mechanistic approach of luciferase catalyzed reactions.  |  Marques, SM. and Esteves da Silva, JC. 2009. IUBMB Life. 61: 6-17. PMID: 18949818
  6. Applications of luciferin biosynthesis: Bioluminescence assays for l-cysteine and luciferase.  |  Niwa, K., et al. 2010. Anal Biochem. 396: 316-8. PMID: 19748476
  7. Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis.  |  Oba, Y., et al. 2013. PLoS One. 8: e84023. PMID: 24391868
  8. Mechanistic model for the firefly luciferin regeneration in biomimetic conditions: a model for the in vivo process?  |  Salatino, CT., et al. 2017. Org Biomol Chem. 15: 3479-3484. PMID: 28379268
  9. An allylated firefly luciferin analogue with luciferase specific response in living cells.  |  Ikeda, Y., et al. 2018. Chem Commun (Camb). 54: 1774-1777. PMID: 29383338
  10. Visualization of mercury(ii) accumulation in vivo using bioluminescence imaging with a highly selective probe.  |  Ke, B., et al. 2018. Org Biomol Chem. 16: 2388-2392. PMID: 29560483
  11. Luciferin Regeneration in Firefly Bioluminescence via Proton-Transfer-Facilitated Hydrolysis, Condensation and Chiral Inversion.  |  Cheng, YY. and Liu, YJ. 2019. Chemphyschem. 20: 1719-1727. PMID: 31090243
  12. Enzymatic promiscuity and the evolution of bioluminescence.  |  Adams, ST. and Miller, SC. 2020. FEBS J. 287: 1369-1380. PMID: 31828943
  13. General Strategy for Bioluminescence Sensing of Peptidase Activity In Vivo Based on Tumor-Targeting Probiotic.  |  Ren, Y., et al. 2021. Anal Chem. 93: 4334-4341. PMID: 33624497
  14. Enhancement of the horseradish peroxidase-catalyzed chemiluminescent oxidation of cyclic diacyl hydrazides by 6-hydroxybenzothiazoles.  |  Thorpe, GH., et al. 1985. Anal Biochem. 145: 96-100. PMID: 4003766

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2-Cyano-6-hydroxybenzothiazole, 10 mg

sc-265653
10 mg
$58.00