ChemicalBook > CAS DataBase List > 2-Cyano-6-hydroxybenzothiazole

2-Cyano-6-hydroxybenzothiazole

Product Name
2-Cyano-6-hydroxybenzothiazole
CAS No.
939-69-5
Chemical Name
2-Cyano-6-hydroxybenzothiazole
Synonyms
D-OH;2-cyano-6-hydroxybenzothiazoL;2-CYANO-6-HYDROXYBENZOTHIAZOLE;6-Hydroxy-Benzothiazole-2-Carb;2-Cyano-6-hydroxy-benzo[d]thiazole;2-Cyano-6-hydroxy-1,3-benzothiazole;2-Cyano-6-hydroxybenzothiazole, >=95%;6-Hydroxy-2-Benzothiazolecarbonitrile;2-Benzothiazolecarbonitrile, 6-hydroxy;6-hydroxy-benzothiazole-2-carbonitrile
CBNumber
CB6466639
Molecular Formula
C8H4N2OS
Formula Weight
176.2
MOL File
939-69-5.mol
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2-Cyano-6-hydroxybenzothiazole Property

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)
pka
7.52±0.40(Predicted)
form 
crystalline solid
color 
Light yellow
InChI
InChI=1S/C8H4N2OS/c9-4-8-10-6-2-1-5(11)3-7(6)12-8/h1-3,11H
InChIKey
SQAVNBZDECKYOT-UHFFFAOYSA-N
SMILES
S1C2=CC(O)=CC=C2N=C1C#N
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36
Safety Statements 
26-36/37
RIDADR 
UN3439
WGK Germany 
3
HS Code 
2934208090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
776823
Product name
6-Hydroxybenzothiazole-2-carbonitrile
Purity
96%
Packaging
500mg
Price
$93.38
Updated
2025/07/31
TCI Chemical
Product number
C3952
Product name
6-Hydroxybenzo[d]thiazole-2-carbonitrile
Packaging
1G
Price
$120
Updated
2025/07/31
TRC
Product number
C998385
Product name
2-Cyano-6-hydroxybenzothiazole
Packaging
50mg
Price
$45
Updated
2021/12/16
TRC
Product number
C998385
Product name
2-Cyano-6-hydroxybenzothiazole
Packaging
100mg
Price
$60
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC09476
Product name
2-Cyano-6-hydroxybenzothiazole
Packaging
1g
Price
$75
Updated
2021/12/16
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2-Cyano-6-hydroxybenzothiazole Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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2-Cyano-6-hydroxybenzothiazole Suppliers

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View Lastest Price from 2-Cyano-6-hydroxybenzothiazole manufacturers

Shaanxi Dideu New Materials Co. Ltd
Product
2-Cyano-6-hydroxybenzothiazole 939-69-5
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000KGS
Release date
2025-02-22
ARCTIC EXPORTS INC
Product
2-Cyano-6-hydroxybenzothiazole 939-69-5
Price
US $1.00/kg
Min. Order
100kg
Purity
99%
Supply Ability
1000000
Release date
2024-01-05
Honest Joy Holdings Limited
Product
2-Cyano-6-hydroxybenzothiazole 939-69-5
Price
US $0.00/KG
Min. Order
1KG
Purity
98.5%
Supply Ability
100 tons
Release date
2022-02-21

939-69-5, 2-Cyano-6-hydroxybenzothiazoleRelated Search:

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

  • 2-CYANO-6-HYDROXYBENZOTHIAZOLE
  • 2-Benzothiazolecarbonitrile, 6-hydroxy
  • 6-Hydroxy-2-Benzothiazolecarbonitrile
  • 6-Hydroxy-Benzothiazole-2-Carb
  • 2-cyano-6-hydroxybenzothiazoL
  • 2-Benzothiazolecarbonitrile,6-hydroxy-(7CI,8CI,9CI)
  • 6-hydroxy-benzothiazole-2-carbonitrile
  • 6-hydroxy-1,3-benzothiazole-2-carbonitrile
  • 2-Cyano-6-hydroxy-1,3-benzothiazole
  • 6-Hydroxybenzothiazole-2-carbonitrile 96%
  • 2-Cyano-6-hydroxybenzothiazole, >=95%
  • D-OH
  • 6-hydroxy-2-Benzothiazolecarbonitrile USP/EP/BP
  • 2-Benzothiazolecarbonitrile, 6-hydroxy- USP/EP/BP
  • 6-hydroxy-1,3-benzothiazole-2-carbonitrile(939-69-5)
  • 2-Cyano-6-hydroxy-benzo[d]thiazole
  • 939-69-5
  • 939-65-9
  • Sulphur Derivatives
  • BENZOTHIAZOLE