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-1,3-benzothiazole;2-Cyano-6-hydroxybenzothiazole, >=95%;6-Hydroxy-2-Benzothiazolecarbonitrile;2-Benzothiazolecarbonitrile, 6-hydroxy;6-hydroxy-benzothiazole-2-carbonitrile;6-Hydroxybenzothiazole-2-carbonitrile 96%
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)
form: crystalline solid
pka: 7.52±0.40(Predicted)
color: Light yellow
InChIKey: SQAVNBZDECKYOT-UHFFFAOYSA-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: $68.4
Updated: 2024/03/01

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

SynQuest Laboratories

Product number: 8H37-1-Y2
Product name: 6-Hydroxy-1,3-benzothiazole-2-carbonitrile
Purity: 97%
Packaging: 5G
Price: $368
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FC09476
Product name: 2-Cyano-6-hydroxybenzothiazole
Packaging: 10g
Price: $370
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

Canada 3 China 170 Europe 1 Germany 5 India 9 Japan 1 Russia 1 Slovakia 1 Switzerland 1 Ukraine 1 United Kingdom 9 United States 19 Global 221

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

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

Zhuozhou Wenxi import and Export Co., Ltd

Product: 2-CYANO-6-HYDROXYBENZOTHIAZOLE 939-69-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

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

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

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6-Hydroxy-2-Benzothiazolecarbonitrile

6-Hydroxy-Benzothiazole-2-Carb

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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)

939-69-5

Sulphur Derivatives

BENZOTHIAZOLE