3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid

Base Information

• Chemical Name: 3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid
• CAS No.: 6948-33-0
• Molecular Formula: C10H9 Br O4
• Molecular Weight: 273.083
• Hs Code.: 2918990090
• European Community (EC) Number: 863-567-0
• NSC Number: 55760
• Nikkaji Number: J364.526F
• Wikidata: Q106902698
• ChEMBL ID: CHEMBL450003
• Mol file: 6948-33-0.mol

Synonyms:6948-33-0;3-(3-bromo-4-hydroxy-5-methoxyphenyl)acrylic acid;5-Bromoferulic acid;3-BROMO-4-HYDROXY-5-METHOXYCINNAMIC ACID;NSC55760;3-(3-Bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid;CHEMBL450003;948051-10-3;(E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid;(E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)acrylic acid;(2E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid;(2E)-3-(3-bromo-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid, E;MLS000775620;HMS1409A10;HMS2760O11;BDBM50479629;MFCD00017334;NSC-55760;STK398187;AKOS000263550;SMR000370511;TS-03525;CS-0168668;CS-0368497;EN300-17290;3-(3-bromo-4-hydroxy-5-methoxyphenyl)acrylicacid;J-510588;Z56911947;2-Propenoic acid,3-(3-bromo-4-hydroxy-5-methoxyphenyl)-;(E)-3-(3-bromo-4-hydroxy-5-methoxy-phenyl)prop-2-enoic acid;(E)-3-(3-BROMO-4-HYDROXY-5-METHOXYPHENYL)-2-PROPENOIC ACID;3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid(predominantly trans)

Chemical Property of 3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid

Chemical Property:

• Vapor Pressure: 1.72E-06mmHg at 25°C
• Melting Point: 255 °C
• Boiling Point: 381.2oC at 760 mmHg
• Flash Point: 184.4oC
• PSA: 66.76000
• Density: 1.668
• LogP: 2.26110
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 271.96842
• Heavy Atom Count: 15
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC(=C1)C=CC(=O)O)Br)O
• Isomeric SMILES: COC1=C(C(=CC(=C1)/C=C/C(=O)O)Br)O

Technology Process of 3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid

There total 2 articles about 3-(3-Bromo-4-hydroxy-5-methoxyphenyl)acrylic acid 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: 71.9%

malonic acid (141-82-2) + 5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → trans-3-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-propenoic acid (6948-33-0)

Guidance literature:

With pyridine; aniline; In toluene; for 2h; Reflux;

DOI:10.1016/j.bmcl.2008.10.046

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) + acetic anhydride (108-24-7) → trans-3-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-propenoic acid (6948-33-0)

Guidance literature:

With sodium acetate; anschliessend Erwaermen mit Wasser;

Reference yield: 80.0%

trans-3-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-propenoic acid (6948-33-0) + tyramine hydrochloride (60-19-5) → C18H18BrNO4

Guidance literature:

trans-3-(5-bromo-4-hydroxy-3-methoxyphenyl)-2-propenoic acid; With 1-hydroxy-pyrrolidine-2,5-dione; In acetonitrile; for 0.0833333h;

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; for 20h; Cooling with ice;

tyramine hydrochloride; With triethylamine; In acetonitrile; at 20 ℃; for 8h;

DOI:10.1002/cjoc.201500054

upstream raw materials:

malonic acid

5-bromo-4-hydroxy-3-methoxybenzaldehyde

acetic anhydride

Downstream raw materials:

methyl 3-methoxy-4-hydroxy-5-bromocinnamate

methyl 3-methoxy-4-hydroxy-5-bromo-cinnamate

3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeuremethylester

3-Methoxy-4-hydroxy-5-brom-hydrozimtsaeure-hydrazid

Refernces

• 1、 Gaspar, Alexandra,Garrido, E. Manuela,Esteves, Mario,Quezada, Elias,Milhazes, Nuno,Garrido, Jorge,Borges, Fernanda. "New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives". experimental part. p. 2092 - 2099. Retrieved 2009/09/08.