4-Chloro-3-nitroquinoline

Base Information

• Chemical Name: 4-Chloro-3-nitroquinoline
• CAS No.: 39061-97-7
• Molecular Formula: C9H5ClN2O2
• Molecular Weight: 208.604
• Hs Code.: 29334900
• European Community (EC) Number: 852-888-1
• DSSTox Substance ID: DTXSID60460883
• Wikidata: Q72456153
• Mol file: 39061-97-7.mol

Synonyms:4-Chloro-3-nitroquinoline;39061-97-7;4-chloro-3-nitro-quinoline;Quinoline, 4-chloro-3-nitro-;MFCD07369246;3-nitro-4-chloroquinoline;4chloro-3-nitroquinoline;4-Chlor-3-nitrochinolin;4-Chloro-3-Nitro Quinoline;SCHEMBL202663;4-chloranyl-3-nitro-quinoline;DTXSID60460883;ZRFUZDDJSQVQBY-UHFFFAOYSA-N;AMY14303;AKOS005217094;AC-1520;CS-W008830;SB71449;AS-17381;SY027642;FT-0639518;EN300-86218;A22832;A824388;J-515031

Chemical Property of 4-Chloro-3-nitroquinoline

Chemical Property:

• Appearance/Colour: yellow crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 121-122°C
• Refractive Index: 1.688
• Boiling Point: 333.757 °C at 760 mmHg
• PKA: -0.28±0.24(Predicted)
• Flash Point: 155.651 °C
• PSA: 58.71000
• Density: 1.484 g/cm³
• LogP: 3.31960
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 208.0039551
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

98.0%Min ^*data from raw suppliers

4-Chloro-3-nitroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(C=N2)[N+](=O)[O-])Cl
• Uses: 4-Chloro-3-nitroquinoline (cas# 39061-97-7) is a compound useful in organic synthesis.

Technology Process of 4-Chloro-3-nitroquinoline

There total 8 articles about 4-Chloro-3-nitroquinoline 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: 93.0%

3-nitro-quinolin-4-ol (50332-66-6) → 4-chloro-3-nitroquinoline (39061-97-7)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; Reflux; Cooling with ice;

Reference yield:

quinolin-4-ol (611-36-9) → 4-chloro-3-nitroquinoline (39061-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / aq. HNO₃ / propionic acid / 0.25 h / 125 °C

2: SOCl₂; DMF / CH₂Cl₂ / 3 h / Heating

With thionyl chloride; nitric acid; N,N-dimethyl-formamide; In dichloromethane; propionic acid;

DOI:10.1021/jm049211v

Reference yield:

2-<2-nitroethylideneamino>benzoic acid (121845-92-9) → 4-chloro-3-nitroquinoline (39061-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / Ac₂O; CH₃COOK

2: 81 percent / POCl₃

With potassium acetate; acetic anhydride; trichlorophosphate;

DOI:10.1021/jm060086s

upstream raw materials:

3-nitro-quinolin-4-ol

3-nitro-4-(1H)-quinolone

2-<2-nitroethylideneamino>benzoic acid

anthranilic acid hydrochloride

Downstream raw materials:

3-nitro-N-phenylquinolin-4-amine

3-amino-4-chloroquinoleine

3-nitro-4-aminoquinoline

1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Refernces

• 1、 Kansal, Sushil K.,Kaur, Manpreet,Kaushik, Deepender,Mehta, Surinder K.,Mutreja, Vishal,Pathania, Khushboo,Pawar, Sandip V.,Sahoo, Subash Chandra,Saini, Vaneet,Salunke, Deepak B.. "Synthesis of quinoline based molecular probes for detection of nitric oxide". . . Retrieved 2022/03/31.
• 2、 -. "LOCALLY ACTING TOLL-LIKE RECEPTOR 7 (TLR7) AND/OR TLR8 AGONIST IMMUNOTHERAPY COMPOUNDS AND THEIR USES". Paragraph 0031-0032; 00181-00182; 00186-00187; 00190. . Retrieved 2020/10/19.