1-(2-Thiazolylazo)-2-naphthol

Base Information

• Chemical Name: 1-(2-Thiazolylazo)-2-naphthol
• CAS No.: 1147-56-4
• Molecular Formula: C13H9N3OS
• Molecular Weight: 255.3
• Hs Code.: 2934100090
• European Community (EC) Number: 214-555-3
• NSC Number: 139021
• DSSTox Substance ID: DTXSID7061566
• Nikkaji Number: J7.283D
• Pharos Ligand ID: A369N4H37B19,A36LK9BMM4M6
• ChEMBL ID: CHEMBL2094383,CHEMBL1511179
• Mol file: 1147-56-4.mol

Synonyms:1-(2-thiazolylazo)-2-naphthol;1-TANP;ERGi-USU;NSC139021

Chemical Property of 1-(2-Thiazolylazo)-2-naphthol

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 138-139 °C
• Refractive Index: 1.728
• Boiling Point: 464.8 °C at 760 mmHg
• PKA: 8.71±0.50(Predicted)
• Flash Point: 234.9 °C
• PSA: 86.08000
• Density: 1.4 g/cm³
• LogP: 4.41730
• Storage Temp.: 2-8°C
• Solubility.: methanol: 10 mg/mL, clear
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 255.04663309
• Heavy Atom Count: 18
• Complexity: 313

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(2-Thiazolylazo)-2-naphthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2N=NC3=NC=CS3)O
• Description: ERGi-USU (1147-56-4) selectively inhibits the growth of ERG-positive VCaP prostate cancer cells, COLO320 colon cancer cells, KG-1 and MOLT-4 leukemia cells with minimal effect on ERG-negative cells or normal prostate or endothelial cells (IC50 = 169 nM for cell growth and 315 nM for ERG protein in VCaP cells). It selectively inhibits the kinase RIOK2 (Kd = 200 nM) causing disruption of ribosomal biogenesis and ribosomal stress.
• Uses: 1-(2-Thiazolylazo)-2-naphthol is a high affinity Rio Kinase 2 (RIOK2) inhibitor (Kd = 200 nM). Exhibits >6-fold selectivity for RIOK2 over a panel of 456 kinases. Inhibits ERG protein and potently inhibits growth of ERG-positive VCaP prostate cancer cells in vitro (IC50 = 169 nM) but not ERG-negative cell lines. Also inhibits growth of VCaP xenografts in mice.

Technology Process of 1-(2-Thiazolylazo)-2-naphthol

There total 1 articles about 1-(2-Thiazolylazo)-2-naphthol 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: 79.0%

2-thiazolylamine (96-50-4) + β-naphthol (135-19-3) → 1-(2-thiazolylazo)-2-naphthol (1147-56-4)

Guidance literature:

2-thiazolylamine; With nitrosylsulfuric acid;

β-naphthol; With phosphoric acid; In methanol; acetic acid; propionic acid; at 0 ℃; Cooling;

DOI:10.5560/ZNB.2014-4001

Reference yield: 100.0%

1-(2-thiazolylazo)-2-naphthol (1147-56-4) + toluene-4-sulfonic acid (104-15-4) → naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazin-4-ium tosylate (1638770-49-6)

Guidance literature:

In acetic acid; for 3h; Reflux;

DOI:10.5560/ZNB.2014-4001

Reference yield:

1-(2-thiazolylazo)-2-naphthol (1147-56-4) + 2,4-Dinitrophenol (51-28-5) → C13H9N3OS*C6H4N2O5

Guidance literature:

In methanol; for 2h;

DOI:10.1016/j.molliq.2017.09.124

upstream raw materials:

2-thiazolylamine

β-naphthol

Downstream raw materials:

8,8-diphenoxy-8λ⁵-naphtho[1',2':4,5][1,3,2]oxazaphospholo[3,2-b]thiazolo[3,2-d][1,2,4,3]triazaphosphole

8,8-diphenyl-8λ⁵-naphtho[1',2':4,5][1,3,2]oxazaphospholo[3,2-b]thiazolo[3,2-d][1,2,4,3]triazaphosphole

naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazin-4-ium tosylate

Refernces

• 1、 Gandhi, M. H.,Pathak, K. C.,Parikh, D. J.,Lahiri, S. A.. "Thiazolylazo Dyes as Reagents for Detection and Ring Colorimetric Determination of Copper". . p. 499 - 500. Retrieved 2007/10/02.