N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide

Base Information

• Chemical Name: N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide
• CAS No.: 978-62-1
• Molecular Formula: C15H8ClF6NO2
• Molecular Weight: 383.677
• Hs Code.: 29242990
• European Community (EC) Number: 635-542-2
• UNII: 76145IS906
• DSSTox Substance ID: DTXSID50243248
• Nikkaji Number: J2.260.032J
• Wikidata: Q27165022
• Pharos Ligand ID: TUWQRU8ZYKRN
• ChEMBL ID: CHEMBL536151
• Mol file: 978-62-1.mol

Synonyms:IMD 0354;IMD-0354;IMD0354;N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide

Chemical Property of N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide

Chemical Property:

• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.543
• Boiling Point: 323.1 °C at 760 mmHg
• PKA: 7.61±0.43(Predicted)
• Flash Point: 149.2 °C
• PSA: 49.33000
• Density: 1.561 g/cm³
• LogP: 5.40850
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Solubility.: Solubility: DMSO (5 mg/ml) or Ethanol (1 mg/ml).
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 383.0147752
• Heavy Atom Count: 25
• Complexity: 462

Purity/Quality:

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

IMD0354 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)C(=O)NC2=CC(=CC(=C2)C(F)(F)F)C(F)(F)F)O
• Uses: IMD 0354 is an IKKβ (IKK2) inhibitor that blocks NF-κB phosphorylation (IC50 = ~250 nM) and subsequent NF-κB p65 nuclear translocation. It exhibits cardioprotective properties by decreasing expression of P-selectin and ICAM-1 in the vasculature and blocking cardiomyocyte IL-1β and MCP-1 production, resulting in suppressed neutrophil accumulation in a rat model of ischemia/reperfusion injury. IMD 0354, suppresses the growth of human breast cancer cells by inducing cell cycle arrest and apoptosis. It induces apoptosis of chronic lymphocytic leukemia cells at 1-10 μM by directly targeting the NF-κB pathway, decreasing expression of anti-apoptotic genes and increasing expression of proapoptotic genes. IMD-0354 has been used to study the effect of NF-κB (nuclear factor) inhibition on differentially expressed in chondrocytes 2. It has also been used to study the role of NF-κB signaling in tumor necrosis factor-induced certain transcription factors expression using human primary fibroblasts.

Technology Process of N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide

There total 6 articles about N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide 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: 85.5%

5-chloro-2-hydroxybenzoic acid (321-14-2) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → N-(3,5-bistrifluoromethylphenyl)-5-chloro-2-hydroxybenzamide (978-62-1)

Guidance literature:

Reference yield: 85.5%

→ N-(3,5-bistrifluoromethylphenyl)-5-chloro-2-hydroxybenzamide (978-62-1)

Guidance literature:

Reference yield:

5-chloro-2-hydroxybenzoyl chloride (15216-81-6) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → N-(3,5-bistrifluoromethylphenyl)-5-chloro-2-hydroxybenzamide (978-62-1)

Guidance literature:

In dichloromethane; at 25 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2019.06.023

upstream raw materials:

5-chloro-2-hydroxybenzoic acid

3,5-Bis-(trifluoromethyl)aniline

5-chloro-2-hydroxybenzoyl chloride

5-chloro-2-methoxybenzoic acid

Downstream raw materials:

C₂₉H₂₁ClF₆NO₅P

C₁₅H₈ClF₆NO₅P^(1-)*Na⁽¹⁺⁾

2-{[3,5-bis(trifluoromethyl)phenyl]carbamoyl}-4-chlorophenyl dihydrogen phosphate

Refernces

• 1、 Tian, Maoqun,Abdelrahman, Aliaa,Baqi, Younis,Fuentes, Eduardo,Azazna, Djamil,Spanier, Claudia,Densborn, Sabrina,Hinz, Sonja,Schmid, Ralf,Müller, Christa E.. "Discovery and Structure Relationships of Salicylanilide Derivatives as Potent, Non-acidic P2X1 Receptor Antagonists". . p. 6164 - 6178. Retrieved 2020/07/10.
• 2、 Krátky, Martin,?těpánková, ?árka,Houngbedji, Neto-Honorius,Vosátka, Rudolf,Vor?áková, Katarína,Vin?ová, Jarmila. "2-Hydroxy-N-Phenylbenzamides and their esters inhibit acetylcholinesterase and Butyrylcholinesterase". . . Retrieved 2019/11/20.