Naphtho[1,2-d]thiazol-2-amine

Base Information

• Chemical Name: Naphtho[1,2-d]thiazol-2-amine
• CAS No.: 40172-65-4
• Molecular Formula: C11H8N2S
• Molecular Weight: 200.264
• Hs Code.: 2934999090
• European Community (EC) Number: 254-822-1
• NSC Number: 6278
• UNII: SW12CAS9T7
• DSSTox Substance ID: DTXSID2068216
• Nikkaji Number: J308.261J
• Wikidata: Q27088806
• Pharos Ligand ID: 8186WD19JSKC
• ChEMBL ID: CHEMBL1709719
• Mol file: 40172-65-4.mol

Synonyms:naphtho(1,2-d)thiazol-2-ylamine;SKA-31

Chemical Property of Naphtho[1,2-d]thiazol-2-amine

Chemical Property:

• Vapor Pressure: 3.63E-07mmHg at 25°C
• Melting Point: 184-188oC
• Boiling Point: 417.1°C at 760 mmHg
• PKA: 3.50±0.30(Predicted)
• Flash Point: 206.1°C
• PSA: 67.15000
• Density: 1.403g/cm³
• LogP: 3.61290
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥30mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 200.04081944
• Heavy Atom Count: 14
• Complexity: 221

Purity/Quality:

99.0% ^*data from raw suppliers

SKA 31 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-36-22
• Safety Statements: 22-36/37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=C2N=C(S3)N
• Description: SKA-31 (40172-65-4) is a KCa3.1 and KCa2 potassium channel activator (EC50 =260, 2900, 2900 nM for KCa3.1, KCa2.1 and KCa2.2 respectively). Enhanced acetylcholine-induced EDHF dilator response in mouse carotid arteries and lowers blood pressure in mouse models at 30 mg/Kg.1,2 Evokes robust vasodilation in rat mesenteric arteries.3

Technology Process of Naphtho[1,2-d]thiazol-2-amine

There total 9 articles about Naphtho[1,2-d]thiazol-2-amine 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: 88.0%

thiourea (17356-08-0) + 3,4-dihydronaphthalene-1(2H)-one (529-34-0) → SKA-31 (40172-65-4)

Guidance literature:

With iodine; oxygen; toluene-4-sulfonic acid; In dimethyl sulfoxide; at 75 ℃; for 24h; under 760.051 Torr;

DOI:10.1021/ol400773k

Reference yield: 82.0%

naphthalen-1-yl-thiourea (86-88-4) → SKA-31 (40172-65-4)

Guidance literature:

With bromine;

DOI:10.1002/ardp.19823151010

Reference yield: 61.5%

potassium thioacyanate (333-20-0) + 1-amino-naphthalene (134-32-7) → SKA-31 (40172-65-4)

Guidance literature:

With bromine; acetic acid; at 25 - 35 ℃; for 20h;

DOI:10.1016/j.molliq.2013.08.021

upstream raw materials:

N,N'-bis(1-naphthyl)thiourea

1-naphthylthiosemicarbazide

naphthalen-1-yl-thiourea

2-aminobenzo-4,5-dihydrobenzothiazole

Downstream raw materials:

phenyl N-(naphtho[1,2-d]thiazol-2-yl)carbamate

3-{3-[4-(4-Fluoro-phenyl)-piperazin-1-yl]-propyl}-1H-naphtho[2,1-b][1,4]thiazin-2-one

Refernces

• 1、 Zhao, Jinwu,Huang, Huawen,Wu, Wanqing,Chen, Huoji,Jiang, Huanfeng. "Metal-free synthesis of 2-aminobenzothiazoles via aerobic oxidative cyclization/dehydrogenation of cyclohexanones and thioureas". supporting information. p. 2604 - 2607. Retrieved 2013/07/11.
• 2、 Azam, Faizul,Alkskas, Ismail A.,Khokra, Sukhbir Lal,Prakash, Om. "Synthesis of some novel N4-(naphtha[1,2-d]thiazol-2-yl)semicarbazides as potential anticonvulsants". experimental part. p. 203 - 211. Retrieved 2009/04/07.