2-Chloro-5-nitro-N-phenylbenzamide

Base Information

• Chemical Name: 2-Chloro-5-nitro-N-phenylbenzamide
• CAS No.: 22978-25-2
• Molecular Formula: C13H9 Cl N2 O3
• Molecular Weight: 276.679
• Hs Code.: 2924299090
• European Community (EC) Number: 636-590-7
• UNII: UM18UZV2YD
• DSSTox Substance ID: DTXSID8040723
• Nikkaji Number: J1.074.057F
• Wikidata: Q27077962
• Pharos Ligand ID: RSL6U4Z5M277
• Metabolomics Workbench ID: 151018
• ChEMBL ID: CHEMBL375270
• Mol file: 22978-25-2.mol

Synonyms:2-chloro-5-nitrobenzanilide;GW-9662;GW9662

Chemical Property of 2-Chloro-5-nitro-N-phenylbenzamide

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 2.15E-05mmHg at 25°C
• Melting Point: 171-175?°C(lit.)
• Boiling Point: 360.9°Cat760mmHg
• PKA: 11.77±0.70(Predicted)
• Flash Point: 172°C
• PSA: 74.92000
• Density: 1.44g/cm³
• LogP: 4.09670
• Storage Temp.: 2-8°C
• Solubility.: DMSO: 26 mg/mL, soluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 276.0301698
• Heavy Atom Count: 19
• Complexity: 339

Purity/Quality:

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

2-Chloro-5-nitro-N-4-phenylbenzamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 26-36/37-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)NC(=O)C2=C(C=CC(=C2)[N+](=O)[O-])Cl
• Description: GW-9662 (22978-25-2) is a selective PPARγ antagonist (IC50 = 3.3, 32 and 2000 nM for PPARγ, PPARα and PPARδ respectively).1 Blocks the inhibition of osteoclast formation induced by IL-4 (1-2 μM).2 Displays anticancer activity inhibits growth of human mammary tumor cell lines.3 GW-9662 is a useful tool for dissecting the involvement of PPARγ in cellular physiology.4,5
• Uses: An irreversible PPAR antagonist GW9662 has been used as a peroxisome proliferator activated receptor γ (PPARγ) antagonist in human pluripotent stem cells, in phenylephrine stimulated cardiomyocytes and to inhibit the protective effect of telmisartan pheochromocytoma, PC12 cells. A cell-permeable, selective and irreversible PPAR antagonist (IC50 = 3.3 nM, 32 nM, and 2 for PPAR, PPARa, and PPARd, respectively). Reported to covalently modify a cysteine residue in the binding site of PPAR. At a concentration of 10 , also

Technology Process of 2-Chloro-5-nitro-N-phenylbenzamide

There total 3 articles about 2-Chloro-5-nitro-N-phenylbenzamide 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: 90.0%

2-chloro-5-nitrobenzoylchloride (25784-91-2) + aniline (62-53-3) → 2-chloro-5-nitrobenzanilide (22978-25-2)

Guidance literature:

With pyridine; at 0 - 20 ℃;

DOI:10.1021/jo801319x

Reference yield: 66.0%

2-chloro-5-nitrobenzoic acid (2516-96-3) + aniline (62-53-3) → 2-chloro-5-nitrobenzanilide (22978-25-2)

Guidance literature:

2-chloro-5-nitrobenzoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 0.166667h;

aniline; Further stages.; Heating;

DOI:10.1016/j.bmc.2007.03.074

Reference yield:

diethyl ether (60-29-7,927820-24-4) + phosphorus pentachloride (10026-13-8,874483-75-7) + 2-chloro-5-nitro-benzophenone oxime (141883-38-7) → 2-chloro-5-nitrobenzanilide (22978-25-2)

Guidance literature:

upstream raw materials:

2-chloro-5-nitrobenzoylchloride

aniline

diethyl ether

phosphorus pentachloride

Downstream raw materials:

2-methoxy-5-nitro-benzoic acid anilide

6-chloro-2-nitro-10-phenyldibenzo[b,f][1,4]thiazepin-11(10H)-one

8-nitro-11-phenyl-3-(trifluoromethyl)benzo[f]pyrido[3,2-b][1,4]thiazepin-10(11H)one

N-(N-(4-chloro-3-(phenylcarbamoyl)phenyl)carbamimidoyl)-3,4,5-trimethoxybenzamide

Refernces

• 1、 Robarge, Kirk D.,Brunton, Shirley A.,Castanedo, Georgette M.,Cui, Yong,Dina, Michael S.,Goldsmith, Richard,Gould, Stephen E.,Guichert, Oivin,Gunzner, Janet L.,Halladay, Jason,Jia, Wei,Khojasteh, Cyrus,Koehler, Michael F.T.,Kotkow, Karen,La, Hank,LaLonde, Rebecca L.,Lau, Kevin,Lee, Leslie,Marshall, Derek,Marsters Jr., James C.,Murray, Lesley J.,Qian, Changgeng,Rubin, Lee L.,Salphati, Laurent,Stanley, Mark S.,Stibbard, John H.A.,Sutherlin, Daniel P.,Ubhayaker, Savita,Wang, Shumei,Wong, Susan,Xie, Minli. "GDC-0449-A potent inhibitor of the hedgehog pathway". scheme or table. p. 5576 - 5581. Retrieved 2010/04/05.
• 2、 -. "Method for the treatment of breast cancer". Page/Page column 4. . Retrieved 2008/12/08.