N-(2-Cyclohexyloxy-4-nitrophenyl)methanesulfonamide

Base Information

• Chemical Name: N-(2-Cyclohexyloxy-4-nitrophenyl)methanesulfonamide
• CAS No.: 123653-11-2
• Molecular Formula: C13H18 N2 O5 S
• Molecular Weight: 314.362
• Hs Code.: 3824909990
• UNII: 9SP55KM2KS
• DSSTox Substance ID: DTXSID8041084
• Nikkaji Number: J541.148C
• Wikipedia: NS-398
• Wikidata: Q6955228
• Pharos Ligand ID: 8S5C11D5RX6Z,8SRPZB8H6YD1
• Metabolomics Workbench ID: 66469
• ChEMBL ID: CHEMBL7162
• Mol file: 123653-11-2.mol

Synonyms:N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide;NS 398;NS-398;NS398

Chemical Property of N-(2-Cyclohexyloxy-4-nitrophenyl)methanesulfonamide

Chemical Property:

• Vapor Pressure: 8.98E-10mmHg at 25°C
• Melting Point: 124-126 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 490.6°Cat760mmHg
• PKA: 6.33±0.10(Predicted)
• Flash Point: 250.5°C
• PSA: 109.60000
• Density: 1.377g/cm³
• LogP: 4.35480
• Storage Temp.: Store at RT
• Solubility.: DMSO: >5 mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 314.09364285
• Heavy Atom Count: 21
• Complexity: 450

Purity/Quality:

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

NS-398 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2CCCCC2
• Description: NS-398 is a selective inhibitor of cyclooxygenase-2 (COX-2). The IC50 values for human recombinant COX-1 and -2 are 75 and 1.77 μM, respectively. The IC50 values for ovine COX-1 and -2 are 220 and 0.15 μM, respectively.
• Uses: NS-398 is a selective Cox-2 inhibitor neuroprotective agent.

Technology Process of N-(2-Cyclohexyloxy-4-nitrophenyl)methanesulfonamide

There total 7 articles about N-(2-Cyclohexyloxy-4-nitrophenyl)methanesulfonamide 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: 59.5%

C14H20N2O7S2 → N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide (123653-11-2)

Guidance literature:

C₁₄H₂₀N₂O₇S₂; With sodium hydroxide; water; at 80 - 90 ℃;

With hydrogenchloride; In water; pH=1 - 2;

Reference yield: 59.5%

2-cyclohexyloxy-4-nitroaniline (183110-93-2) + methanesulfonyl chloride (124-63-0) → N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide (123653-11-2)

Guidance literature:

2-cyclohexyloxy-4-nitroaniline; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

methanesulfonyl chloride; In N,N-dimethyl-formamide; at 20 ℃;

With sodium hydroxide; at 80 - 90 ℃;

DOI:10.1021/jm051126f

Reference yield:

Cyclohexyl iodide (626-62-0) → N-(2-cyclohexyloxy-4-nitrophenyl)methanesulfonamide (123653-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 5 percent / K₂CO₃ / dimethylformamide / 120 h / Heating

2.1: NaH / dimethylformamide / 0.33 h

2.2: 20 °C

3.1: aq. KOH / 2 h / Heating

With potassium hydroxide; sodium hydride; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.065

upstream raw materials:

2-cyclohexyloxy-4-nitroaniline

methanesulfonyl chloride

Cyclohexyl iodide

5-Nitro-2-aminophenol

Refernces

• 1、 Wang, Min,Lacy, Gabrielle,Gao, Mingzhang,Miller, Kathy D.,Sledge, George W.,Zheng, Qi-Huang. "Synthesis of carbon-11 labeled sulfonanilide analogues as new potential PET agents for imaging of aromatase in breast cancer". . p. 332 - 336. Retrieved 2007/10/03.
• 2、 -. "Method for the treatment and prevention of cachexia". . . Retrieved 2008/06/13.