2-Cyano-6-hydroxybenzothiazole Chemical Properties

Melting point:

211-213°C

Boiling point:

374.7±34.0 °C(Predicted)

Density 

1.53±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

crystalline solid

pka

7.52±0.40(Predicted)

color 

Light yellow

InChIKey

SQAVNBZDECKYOT-UHFFFAOYSA-N

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36

Safety Statements 

26-36/37

RIDADR 

UN3439

WGK Germany 

3

HS Code 

2934208090

2-Cyano-6-hydroxybenzothiazole Usage And Synthesis

Description

2-Cyano-6-hydroxybenzothiazole (CBTOH) is a critical intermediate in D-luciferin biosynthesis, also used for its chemical synthesis and as luciferin bioluminescence precursor for chemical analysis. Firefly light emission involves the enzymatic oxidation of D-luciferin to yield electronically excited oxyluciferin, which is the bioluminescent molecule. Oxyluciferin is afterwards enzymatically oxidized to thioglycolic acid and CBTOH, which regenerates luciferin by condensation with cysteine[1].

Synthesis

A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with l-cysteine ethyl ester, followed by oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propan-oate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone)[2].

References

[1] Ankita S. Jadhav . “Firefly luciferin precursor 2-cyano-6-hydroxybenzothiazole: Fluorescence à la carte controlled by solvent and acidity.” Dyes and Pigments 177 (2020): Article 108285.
[2] G. Meroni. “A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1,4-benzoquinone.” Synlett 29 1 (2009): 2682–2684.

2-Cyano-6-hydroxybenzothiazole(939-69-5)Related Product Information

• URANIUM
• 6-Benzothiazolol(7CI,8CI,9CI)
• 2-Cyanothiazole
• 2-Cyano-6-methoxybenzothiazole
• 2-CYANO-6-HYDROXYBENZOTHIAZOLE