2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)-

Base Information

• Chemical Name: 2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)-
• CAS No.: 328956-38-3
• Molecular Formula: C10H5F3N2O3
• Molecular Weight: 258.15
• DSSTox Substance ID: DTXSID00582114
• Wikidata: Q82473436
• Mol file: 328956-38-3.mol

Synonyms:328956-38-3;2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)-;6-NITRO-4-(TRIFLUOROMETHYL)-1H-QUINOLIN-2-ONE;MFCD12828492;4-trifluoromethyl-6-nitroquinolinone;6-Nitro-4-(trifluoromethyl)-2(1H)-quinolinone;SCHEMBL1771140;DTXSID00582114;AKOS015951301;s11905;SY317086;6-Nitro-4-trifluoromethyl-1H-quinolin-2-one;G10412;6-NITRO-4-TRIFLUOROMETHYL-QUINOLIN-2-OL;A875492

Chemical Property of 2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)-

Chemical Property:

• Melting Point: 284-285 °C(Solv: ethanol (64-17-5))
• Boiling Point: 368.7±42.0 °C(Predicted)
• PKA: 9.09±0.70(Predicted)
• PSA: 78.68000
• Density: 1.564±0.06 g/cm3(Predicted)
• LogP: 2.97830
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 258.02522651
• Heavy Atom Count: 18
• Complexity: 414

Purity/Quality:

99% ^*data from raw suppliers

6-Nitro-4-(trifluoromethyl)quinolin-2(1H)-one 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1[N+](=O)[O-])C(=CC(=O)N2)C(F)(F)F
• Uses: 6-Nitro-4-(trifluoromethyl)-2(1H)-quinolinone is an intermediate in the synthesis of LGD-2226 (L397615), an orally active potent and selective androgen receptor modulator used in the treatment of muscle wasting and osteoporosis. Show to have an anabolic effect on muscle and bone tissue.

Technology Process of 2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)-

There total 3 articles about 2(1H)-Quinolinone, 6-nitro-4-(trifluoromethyl)- 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%

4-(trifluoromethyl)quinolin-2(1H)-one (25199-84-2) → 6-nitro-4-trifluoromethylquinolin-2(1H)-one (328956-38-3)

Guidance literature:

With sulfuric acid; nitric acid; at -5 - 10 ℃; for 1h;

DOI:10.1021/jm060792t

Reference yield:

aniline (62-53-3) → 6-nitro-4-trifluoromethylquinolin-2(1H)-one (328956-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene; H₂O / 21 h / 130 °C / Heating

2: 63.4 g / H₂SO₄ / 1.5 h / 80 - 90 °C

3: 93 percent / H₂SO₄; aq. HNO₃ / 1 h / -5 - 10 °C

With sulfuric acid; nitric acid; In water; toluene;

DOI:10.1021/jm060792t

Reference yield:

4,4,4-trifluoro-3-oxo-N-phenylbutyramide (836-31-7) → 6-nitro-4-trifluoromethylquinolin-2(1H)-one (328956-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 63.4 g / H₂SO₄ / 1.5 h / 80 - 90 °C

2: 93 percent / H₂SO₄; aq. HNO₃ / 1 h / -5 - 10 °C

With sulfuric acid; nitric acid;

DOI:10.1021/jm060792t

upstream raw materials:

4-(trifluoromethyl)quinolin-2(1H)-one

aniline

4,4,4-trifluoro-3-oxo-N-phenylbutyramide

Downstream raw materials:

6-amino-4-(trifluoromethyl)quinoline-2-(1H)-one

Refernces

• 1、 Van Oeveren, Arjan,Motamedi, Mehrnouch,Mani, Neelakandha S.,Marschke, Keith B.,López, Francisco J.,Schrader, William T.,Negro-Vilar, Andrés,Zhi, Lin. "Discovery of 6-N,N-Bis(2,2,2-trifluoroethyl)amino-4- trifluoromethylquinolin-2(1H)-one as a novel selective androgen receptor modulator". . p. 6143 - 6146. Retrieved 2007/10/03.