2-Amino-6-methoxybenzothiazole

Base Information

• Chemical Name: 2-Amino-6-methoxybenzothiazole
• CAS No.: 1747-60-0
• Molecular Formula: C8H8N2OS
• Molecular Weight: 180.23
• Hs Code.: 29342080
• European Community (EC) Number: 217-130-0
• NSC Number: 27516
• UNII: LAT2842YVX
• DSSTox Substance ID: DTXSID9024485
• Nikkaji Number: J37.323K
• Wikipedia: 2-amino-6-methoxybenzothiazole
• Wikidata: Q27282899
• ChEMBL ID: CHEMBL97797
• Mol file: 1747-60-0.mol

Synonyms:2-amino-6-methoxybenzothiazole;2-amino-6-methoxybenzothiazole sulfate (1:1)

Chemical Property of 2-Amino-6-methoxybenzothiazole

Chemical Property:

• Appearance/Colour: off-white to tan-coloured powder
• Vapor Pressure: 0.000142mmHg at 25°C
• Melting Point: 165-167 °C(lit.)
• Refractive Index: 1.599
• Boiling Point: 347.455 °C at 760 mmHg
• PKA: pK1: 4.50(+1) (25°C)
• Flash Point: 163.935 °C
• PSA: 76.38000
• Density: 1.36 g/cm³
• LogP: 2.46830
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: very slightly in Methanol
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 180.03573406
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-6-methoxybenzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Thiazoles
• Canonical SMILES: COC1=CC2=C(C=C1)N=C(S2)N
• Uses: 2-Amino-6-methoxybenzothiazole is an intermediate used to prepare novel series of Schiff bases and 4-thiazolidinones. It is also used in the synthesis of 2-cyano-6-methoxybenzothiazole. 2-Amino-6-methoxybenzothiazole was used as building block in the syntheses of novel series of Schiff bases and 4-thiazolidinones. It was used in the synthesis of 2-cyano-6-methoxybenzothiazole, key intermediate for the synthesis of firefly luciferin.

Technology Process of 2-Amino-6-methoxybenzothiazole

There total 23 articles about 2-Amino-6-methoxybenzothiazole 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: 98.0%

potassium thioacyanate (333-20-0) + 4-methoxy-aniline (104-94-9) → 6-methoxybenzothiazol-2-ylamine (1747-60-0)

Guidance literature:

With sodium iodide dichloride; at 70 ℃; for 3h;

DOI:10.1055/s-0032-1317080

Reference yield: 96.0%

ammonium thiocyanate (1147550-11-5) + 4-methoxy-aniline (104-94-9) → 6-methoxybenzothiazol-2-ylamine (1747-60-0)

Guidance literature:

With tris(2,2'-bipyridyl)ruthenium dichloride; In acetonitrile; at 20 ℃; for 10h; Irradiation;

DOI:10.1016/j.tetlet.2020.151700

Reference yield: 93.0%

ammonium thiocyanate + 4-methoxy-aniline (104-94-9) → 6-methoxybenzothiazol-2-ylamine (1747-60-0)

Guidance literature:

With N,N,N-trimethylbenzenemethanaminium dichloroiodate; In water; dimethyl sulfoxide; at 70 ℃; for 1h;

DOI:10.1016/j.tetlet.2021.153388

upstream raw materials:

potassium thioacyanate

4-methoxy-aniline

ammonium thiocyanate

1-(4-methoxyphenyl)thiourea

Downstream raw materials:

6-methoxy-N,N-dimethylbenzo[d]thiazol-2-amine

N-(6-methoxybenzo[d]thiazol-2-yl)acetamide

N-phenyl-N'-(6-methoxy)benzothiazolylthiocarbamide

3-methyl-6-methoxy-2-aminobenzothiazolium chloride

Refernces

• 1、 Rubin et al.. "-". . . Retrieved 1974.
• 2、 Shahmoradi, Ghasem,Amani, Saeid. "Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor". . p. 255 - 258. Retrieved 2018.
• 3、 Ali, Ruhi,Siddiqui, Nadeem. "New Benzo[d]thiazol-2-yl-aminoacetamides as Potential Anticonvulsants: Synthesis, Activity and Prediction of Molecular Properties". . p. 254 - 265. Retrieved 2015.
• 4、 Mishra, Chandra Bhushan,Kumari, Shikha,Angeli, Andrea,Bua, Silvia,Mongre, Raj Kumar,Tiwari, Manisha,Supuran, Claudiu T.. "Discovery of Potent Carbonic Anhydrase Inhibitors as Effective Anticonvulsant Agents: Drug Design, Synthesis, and in Vitro and in Vivo Investigations". . p. 3100 - 3114. Retrieved 2021/04/12.
• 5、 Cai, Jie-Hui,Huang, Qiu-Chan,Huang, Qiu-Ping,Qin, Li-Jin,Wei, You-Huan,Zeng, Zhen-Fang,Zheng, Guang-Jin. "CT-DNA/HSA binding interactions and cytotoxicity activity of a new copper(II) complex". . . Retrieved 2021/09/20.