Methyl 3-(4-nitrophenyl)prop-2-ynoate

Base Information

• Chemical Name: Methyl 3-(4-nitrophenyl)prop-2-ynoate
• CAS No.: 7515-15-3
• Molecular Formula: C10H7NO4
• Molecular Weight: 205.17
• NSC Number: 71090
• DSSTox Substance ID: DTXSID70290799
• Nikkaji Number: J1.059.724B
• Wikidata: Q82028590
• ChEMBL ID: CHEMBL1967778
• Mol file: 7515-15-3.mol

Synonyms:methyl 3-(4-nitrophenyl)propiolate

Chemical Property of Methyl 3-(4-nitrophenyl)prop-2-ynoate

Chemical Property:

• PSA: 72.12000
• LogP: 1.64250
• Storage Temp.: 0-5°C
• Solubility.: DMSO: soluble20mg/mL, clear
• 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: 311

Purity/Quality:

99% ^*data from raw suppliers

p-Nitrophenyl Phosphate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Methyl 3-(4-nitrophenyl)prop-2-ynoate

There total 10 articles about Methyl 3-(4-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: 99.0%

p-nitrobenzene iodide (636-98-6) + propynoic acid methyl ester (922-67-8) → methyl 3-(4-nitrophenyl)-2-propynoate (7515-15-3)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate; In tetrahydrofuran; at 65 ℃; for 2h;

DOI:10.1080/00397919808005726

Reference yield: 61.0%

p-nitrobenzene iodide (636-98-6) + propynoic acid ethyl ester (623-47-2) → methyl 3-(4-nitrophenyl)-2-propynoate (7515-15-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; diisopropylamine; zinc dibromide; In tetrahydrofuran; hexane; at -98 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1039/c8ob01343h

Reference yield: 55.0%

methanol (67-56-1) + (4-Nitrophenyl)acetylene (937-31-5) + carbon monoxide (201230-82-2) → methyl 3-(4-nitrophenyl)-2-propynoate (7515-15-3)

Guidance literature:

With bis(benzonitrile)palladium(II) chloride; silver trifluoromethanesulfonate; N-{(1E,2E)-2-[(2,6-diisopropylphenyl)imino]acenaphthenylidene}-2,6-diisopropylaniline; p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 42h; under 3000.3 Torr; Autoclave; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201600521

upstream raw materials:

methanol

3-(4-nitrophenyl)-2-propynoic acid

methyl (Z)-2-bromo-3-(4-nitrophenyl)-2-propenoate

p-nitrobenzene iodide

Downstream raw materials:

(Z)-2-[Bis-(2-hydroxy-ethyl)-amino]-3-(4-nitro-phenyl)-acrylic acid methyl ester

E-methyl β-(N,N-diethylamino)-p-nitrocinnamate

Z-methyl β-(N,N-diethylamino)-p-nitrocinnamate

5-(4-nitro-phenyl)-isoxazol-3-one