Ethyl 4-nitro-3-(trifluoromethylsulfonyloxy)benzoate

Base Information

• Chemical Name: Ethyl 4-nitro-3-(trifluoromethylsulfonyloxy)benzoate
• CAS No.: 86400-58-0
• Molecular Formula: C₁₀H₈F₃NO₇S
• Molecular Weight: 343.237
• DSSTox Substance ID: DTXSID801201588
• Mol file: 86400-58-0.mol

Synonyms:86400-58-0;SCHEMBL3354100;DTXSID801201588;Ethyl 4-nitro-3-[[(trifluoromethyl)sulfonyl]oxy]benzoate

Chemical Property of Ethyl 4-nitro-3-(trifluoromethylsulfonyloxy)benzoate

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 342.99735725
• Heavy Atom Count: 22
• Complexity: 522

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=C(C=C1)[N+](=O)[O-])OS(=O)(=O)C(F)(F)F

Technology Process of Ethyl 4-nitro-3-(trifluoromethylsulfonyloxy)benzoate

There total 1 articles about Ethyl 4-nitro-3-(trifluoromethylsulfonyloxy)benzoate 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: 85.0%

trifluoromethane sulfonyl chloride (421-83-0) + ethyl 3-hydroxy-4-nitro-benzoate (717-01-1) → 5-carbethoxy-2-nitro-phenyl triflate (86400-58-0)

Guidance literature:

With triethylamine; In acetone; at 25 ℃; for 15h;

Reference yield: 75.0%

5-carbethoxy-2-nitro-phenyl triflate (86400-58-0) + diethyl malonate (105-53-3) → diethyl 5-carbethoxy-2-nitro-benzyl malonate (86400-59-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

Reference yield:

5-carbethoxy-2-nitro-phenyl triflate (86400-58-0) → 5-carboxy-3-benzyl-indolin-2-one (86400-62-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / NaH / dimethylformamide / 24 h / 25 °C

2: 82 percent / iron powder / acetic acid / 2 h / Heating

3: 80 percent / piperidine / ethanol / 2 h / Heating

4: 88 percent / NaBH₄ / ethanol; H₂O / 0.33 h / Heating

5: 90 percent / conc. HCl / acetic acid / 2 h / Heating

With piperidine; hydrogenchloride; sodium tetrahydroborate; iron; sodium hydride; In ethanol; water; acetic acid; N,N-dimethyl-formamide;

upstream raw materials:

trifluoromethane sulfonyl chloride

ethyl 3-hydroxy-4-nitro-benzoate

Downstream raw materials:

diethyl 5-carbethoxy-2-nitro-benzyl malonate

ethyl 2-oxindoline-5-carboxylate

3-benzyl-5-chloromethyl-indolin-2-one

3-benzyl-5-hydroxymethyl-indolin-2-one