Methyl 3-(3-nitrophenyl)prop-2-ynoate

Base Information

• Chemical Name: Methyl 3-(3-nitrophenyl)prop-2-ynoate
• CAS No.: 7515-22-2
• Molecular Formula: C10H7NO4
• Molecular Weight: 205.17
• DSSTox Substance ID: DTXSID601286328
• Mol file: 7515-22-2.mol

Synonyms:7515-22-2;Methyl 3-(3-nitrophenyl)prop-2-ynoate;methyl (3-nitrophenyl)propiolate;DTXSID601286328;Methyl 3-(3-nitrophenyl)-2-propynoate;EN300-743525

Chemical Property of Methyl 3-(3-nitrophenyl)prop-2-ynoate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 205.03750770
• Heavy Atom Count: 15
• Complexity: 319

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C#CC1=CC(=CC=C1)[N+](=O)[O-]

Technology Process of Methyl 3-(3-nitrophenyl)prop-2-ynoate

There total 10 articles about Methyl 3-(3-nitrophenyl)prop-2-ynoate 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: 82.0%

methyl 3-(3-nitrophenyl)-3-oxo-2-(triphenylphosphoranylidene)propanoate (96869-84-0) → methyl 3-(3-nitrophenyl)propiolate (7515-22-2)

Guidance literature:

at 250 ℃; for 0.333333h; under 1 Torr;

DOI:10.1055/s-1994-25402

Reference yield: 52.0%

3-nitrophenylacetylene (3034-94-4) + methyl chloroformate (79-22-1) → methyl 3-(3-nitrophenyl)propiolate (7515-22-2)

Guidance literature:

3-nitrophenylacetylene; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

methyl chloroformate; In tetrahydrofuran; hexane; at -20 ℃; for 1h;

DOI:10.1002/anie.202008572

Reference yield:

m-iodonitrobenzene (645-00-1) + propynoic acid methyl ester (922-67-8) → methyl 3-(3-nitrophenyl)propiolate (7515-22-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80 ℃; for 0.166667h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152378

upstream raw materials:

methanol

3-(3-nitrophenyl)propynoic acid

methyl 3-(3-nitrophenyl)-3-oxo-2-(triphenylphosphoranylidene)propanoate

hydrogenchloride

Downstream raw materials:

3-(3-nitrophenyl)propynoic acid

3-(3-nitrophenyl)-3-oxopropionic acid methyl ester

Refernces

• 1、 Archambeau, Alexis,Cossy, Janine,Meyer, Christophe,Pierre, Hugo,Yamani, Khalil. "Asymmetric Transfer Hydrogenation of gem-Difluorocyclopropenyl Esters: Access to Enantioenriched gem-Difluorocyclopropanes". supporting information. p. 18505 - 18509. Retrieved 2020/08/27.
• 2、 Gomez, Virginia,Perez-Medrano, Arturo,Muchowski, Joseph M.. "Synthesis of β-Dicarbonyl Compounds via the Conjugate Addition of Benzaldoximate Anion to α,β-Acetylenic Carbonyl Compounds". . p. 1219 - 1221. Retrieved 2007/10/02.