2-Cyano-6-hydroxybenzothiazole

Base Information

• Chemical Name: 2-Cyano-6-hydroxybenzothiazole
• CAS No.: 939-69-5
• Molecular Formula: C8H4N2OS
• Molecular Weight: 176.199
• Hs Code.: 2934999090
• European Community (EC) Number: 633-632-6
• DSSTox Substance ID: DTXSID10432318
• Nikkaji Number: J1.613.044C
• Wikidata: Q72458312
• Mol file: 939-69-5.mol

Synonyms:2-Cyano-6-hydroxybenzothiazole;939-69-5;6-hydroxybenzo[d]thiazole-2-carbonitrile;6-hydroxy-1,3-benzothiazole-2-carbonitrile;6-hydroxybenzothiazole-2-carbonitrile;C8H4N2OS;2-Benzothiazolecarbonitrile, 6-hydroxy-;MFCD00296905;6-Hydroxy-benzothiazole-2-carbonitrile;6-hydroxy-2-cyano-benzothiazole;SCHEMBL140656;6-hydroxy-2-cyanobenzothiazole;DTXSID10432318;SQAVNBZDECKYOT-UHFFFAOYSA-N;BBL101177;GEO-00837;STL554973;AKOS005257673;AC-7689;CS-W005799;FS-2463;SY065965;6-hydroxy-benzo[d]thiazole-2-carbonitrile;6-hydroxybenzo-[d]thiazole-2-carbonitrile;6-Hydroxybenzothiazole-2-carbonitrile, 96%;AM20041433;FT-0603716;J-509202

Chemical Property of 2-Cyano-6-hydroxybenzothiazole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 211-213°C
• Refractive Index: 1.744
• Boiling Point: 374.657 °C at 760 mmHg
• PKA: 7.52±0.40(Predicted)
• Flash Point: 180.387 °C
• PSA: 85.15000
• Density: 1.53 g/cm³
• LogP: 1.87358
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 176.00443393
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

99.0% ^*data from raw suppliers

2-Cyano-6-hydroxybenzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1O)SC(=N2)C#N

Technology Process of 2-Cyano-6-hydroxybenzothiazole

There total 20 articles about 2-Cyano-6-hydroxybenzothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-cyano-6-methoxybenzothiazole (943-03-3) → 2-cyano-6-hydroxybenzothiazole (939-69-5)

Guidance literature:

With pyridine hydrochloride; at 200 ℃;

Reference yield: 90.0%

potassium cyanide + diazonium tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole → 2-cyano-6-hydroxybenzothiazole (939-69-5)

Guidance literature:

potassium cyanide; With dibenzo-18-crown-6; copper(II) tetrafluroborate hexahydrate; copper(l) cyanide; In acetonitrile; for 0.25h;

With N,N,N,N,-tetramethylethylenediamine; In acetonitrile; at 25 ℃; for 0.5h;

diazonium tetrafluoroborate salt of 2-amino-6-hydroxybenzothiazole; In acetonitrile; at 25 ℃; for 1h; Reagent/catalyst; Time; Catalytic behavior; Mechanism; Sealed tube; Inert atmosphere;

DOI:10.3906/kim-1801-76

Reference yield: 83.0%

6-allyloxybenzothiazole-2-carbonitrile (1198094-60-8) → 2-cyano-6-hydroxybenzothiazole (939-69-5)

Guidance literature:

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1055/s-0029-1217971

upstream raw materials:

6-ethoxy-benzothiazole-2-carbonitrile

2-cyano-6-methoxybenzothiazole

6-methoxybenzothiazol-2-ylamine

6-ethoxybenzothiazole-2-sulfonamide

Downstream raw materials:

6-acetoxy-2-cyanobenzothiazole

D-luciferin

(R)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

D-luciferin

Refernces

• 1、 Rylands, Marwaan,Jardine, Anwar. "Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin". . p. 176 - 189. Retrieved 2021/03/17.
• 2、 -. "Bioluminescent probe for detection of selenocysteine in organisms, preparation method and application thereof". Paragraph 0107-0108. . Retrieved 2019/02/13.