4-Nitrobenzoic acid, but-3-yn-2-yl ester

Base Information

• Chemical Name: 4-Nitrobenzoic acid, but-3-yn-2-yl ester
• CAS No.: 99972-67-5
• Molecular Formula: C₁₁H₉NO₄
• Molecular Weight: 219.197
• DSSTox Substance ID: DTXSID501300042
• Nikkaji Number: J2.319.450C
• Mol file: 99972-67-5.mol

Synonyms:4-Nitrobenzoic acid, but-3-yn-2-yl ester;DTXSID501300042;AKOS033238559;3-Butyn-2-ol, 2-(4-nitrobenzoate);4-Nitrobenzoic acid 1-methyl-2-propynyl ester;Z1291436281;99972-67-5

Chemical Property of 4-Nitrobenzoic acid, but-3-yn-2-yl ester

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 317

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C#C)OC(=O)C1=CC=C(C=C1)[N+](=O)[O-]

Technology Process of 4-Nitrobenzoic acid, but-3-yn-2-yl ester

There total 2 articles about 4-Nitrobenzoic acid, but-3-yn-2-yl ester 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: 29.0%

1,2-dibromo-3-(4-nitrobenzoyloxy)butane (791590-34-6) → 4-nitro-benzoic acid-(1-methyl-prop-2-ynyl ester) (42969-24-4,99972-67-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 80 ℃; for 16h;

DOI:10.1016/j.tetlet.2006.04.075 DOI:10.1246/bcsj.80.578

Reference yield:

3-(4-nitrobenzoyloxy)-1-butene (232926-35-1) → 4-nitro-benzoic acid-(1-methyl-prop-2-ynyl ester) (42969-24-4,99972-67-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / pyridine*HBr₃; pyridine / CH₂Cl₂

2: 29 percent / DBU / dimethylformamide / 16 h / 80 °C

With pyridine; pyridinium perbromide hydrobromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.80.578

Reference yield:

4-nitro-benzoic acid-(1-methyl-prop-2-ynyl ester) (42969-24-4,99972-67-5) → 1-(p-Nitrobenzoyloxy)-butadien-(1,2) (42969-41-5)

Guidance literature:

With silver tetrafluoroborate; benzene; In chlorobenzene;

DOI:10.1002/hlca.19730560309

upstream raw materials:

1,2-dibromo-3-(4-nitrobenzoyloxy)butane

3-(4-nitrobenzoyloxy)-1-butene

Downstream raw materials:

1-(p-Nitrobenzoyloxy)-butadien-(1,2)