6-Benzothiazolol, 2-(4-nitrophenyl)-

Base Information

• Chemical Name: 6-Benzothiazolol, 2-(4-nitrophenyl)-
• CAS No.: 480391-86-4
• Molecular Formula: C13H8N2O3S
• Molecular Weight: 272.284
• DSSTox Substance ID: DTXSID60447376
• Nikkaji Number: J2.873.645B
• Wikidata: Q82266241
• ChEMBL ID: CHEMBL4564405
• Mol file: 480391-86-4.mol

Synonyms:6-Benzothiazolol, 2-(4-nitrophenyl)-;480391-86-4;SCHEMBL2062033;CHEMBL4564405;DTXSID60447376;GYQGDDBYYWQCAW-UHFFFAOYSA-N;2-(4-Nitrophenyl)benzothiazole-6-ol;2-(4-nitrophenyl)benzo[d]thiazol 6-ol;2-(4-nitrophenyl)benzo[d]thiazol-6-ol;2-(4-Nitrophenyl)-6-hydroxybenzothiazole;2-(4'-Nitrophenyl)-6-hydroxybenzothiazole;2-(4'-nitrophenyl)-6-hydroxy benzothiazole

Chemical Property of 6-Benzothiazolol, 2-(4-nitrophenyl)-

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 272.02556330
• Heavy Atom Count: 19
• Complexity: 341

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=NC3=C(S2)C=C(C=C3)O)[N+](=O)[O-]

Technology Process of 6-Benzothiazolol, 2-(4-nitrophenyl)-

There total 8 articles about 6-Benzothiazolol, 2-(4-nitrophenyl)- 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%

6-methoxy-2-(4-nitrophenyl)benzothiazole (43036-14-2) → 6-hydroxy-2-(4'-nitrophenyl)-1,3-benzothiazole (480391-86-4)

Guidance literature:

With pyridine hydrochloride; at 200 ℃; for 4h;

Reference yield: 87.0%

6-hydroxy-2-bromo-benzothiazole (808755-67-1) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene (171364-83-3) → 6-hydroxy-2-(4'-nitrophenyl)-1,3-benzothiazole (480391-86-4)

Guidance literature:

6-hydroxy-2-bromo-benzothiazole; 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene; With potassium carbonate; In water; N,N-dimethyl-formamide; for 1h; Inert atmosphere;

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; N,N-dimethyl-formamide; at 60 ℃; for 0.25h; Temperature; Time; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.tet.2013.06.085

Reference yield:

N-(4-methoxyphenyl)-4-nitrobenzamide (24730-11-8) → 6-hydroxy-2-(4'-nitrophenyl)-1,3-benzothiazole (480391-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / Lawesson's reagent / chlorobenzene / 3 h / Heating

2: aq. NaOH; K₃Fe(CN)6 / ethanol / 0.5 h / Heating

3: 20 percent / BBr₃ / CH₂Cl₂ / 24 h / 20 °C

With Lawessons reagent; sodium hydroxide; boron tribromide; potassium hexacyanoferrate(III); In ethanol; dichloromethane; chlorobenzene;

DOI:10.1021/jm030026b

upstream raw materials:

6-methoxy-2-(4-nitrophenyl)benzothiazole

N-(4-methoxyphenyl)-4-nitrobenzamide

N-(4-methoxyphenyl)-4-nitrothiobenzamide

4-methoxy-aniline

Downstream raw materials:

C₃₀H₂₆N₂O₅S

C₂₃H₁₉FN₂O₄S