Methyl 5-bromonicotinoylacetate

Base Information

• Chemical Name: Methyl 5-bromonicotinoylacetate
• CAS No.: 205985-97-3
• Molecular Formula: C₉H₈BrNO₃
• Molecular Weight: 258.071
• Hs Code.: 2933399090
• European Community (EC) Number: 674-234-2
• DSSTox Substance ID: DTXSID10371632
• Wikidata: Q82159029
• Mol file: 205985-97-3.mol

Synonyms:Methyl 5-bromonicotinoylacetate;205985-97-3;methyl 3-(5-bromopyridin-3-yl)-3-oxopropanoate;CLAVULANICACID;3-Pyridinepropanoicacid, 5-bromo-b-oxo-,methyl ester;SCHEMBL1477156;DTXSID10371632;YVDRZMXIMURBFZ-UHFFFAOYSA-N;MFCD00216527;AKOS015835059;PS-6108;methyl 5-bromonicotinoylacetate, AldrichCPR;CS-0302063;FT-0706625;F81485;methyl3-(5-bromopyridin-3-yl)-3-oxopropanoate;EN300-1124856;A879543;3-Pyridinepropanoic acid, 5-bromo-beta-oxo-, methyl ester

Chemical Property of Methyl 5-bromonicotinoylacetate

Chemical Property:

• Vapor Pressure: 0.000132mmHg at 25°C
• Melting Point: 88-93oC
• Refractive Index: 1.6200 (estimate)
• Boiling Point: 334°C at 760 mmHg
• PKA: 9.51±0.50(Predicted)
• Flash Point: 155.8°C
• PSA: 56.26000
• Density: 1.546g/cm³
• LogP: 1.58990
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 256.96876
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

97% ^*data from raw suppliers

Methyl5-Bromonicotinoylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(=O)C1=CC(=CN=C1)Br

Technology Process of Methyl 5-bromonicotinoylacetate

There total 4 articles about Methyl 5-bromonicotinoylacetate 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: 62.0%

3-acetyl-5-bromopyridine (38940-62-4) + carbonic acid dimethyl ester (616-38-6) → methyl (5-bromopyridin-3-yl)-3-oxopropanoate (205985-97-3)

Guidance literature:

carbonic acid dimethyl ester; With sodium hydride; In tetrahydrofuran; at 70 ℃; for 2h;

3-acetyl-5-bromopyridine; In tetrahydrofuran; at 70 ℃; for 12h;

Reference yield:

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + monomethyl monopotassium malonate (38330-80-2) → methyl (5-bromopyridin-3-yl)-3-oxopropanoate (205985-97-3)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 1h;

With triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

monomethyl monopotassium malonate; With magnesium chloride; In tetrahydrofuran; at 20 ℃; for 11h;

Reference yield:

5-bromo-3-pyridinecarboxylic acid (20826-04-4) + monomethyl monopotassium malonate (38330-80-2) → methyl (Z)-3-(5-bromo-3-pyridyl)-3-hydroxyprop-2-enoate + methyl (5-bromopyridin-3-yl)-3-oxopropanoate (205985-97-3)

Guidance literature:

5-bromo-3-pyridinecarboxylic acid; With triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 30 ℃; for 1h; Inert atmosphere;

monomethyl monopotassium malonate; With magnesium chloride; In tetrahydrofuran; at 30 ℃; for 16h;

upstream raw materials:

5-bromo-3-pyridine carboxylic acid methyl ester

acetic acid methyl ester

3-acetyl-5-bromopyridine

carbonic acid dimethyl ester