3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid

Base Information

• Chemical Name: 3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid
• CAS No.: 4698-21-9
• Molecular Formula: C12H12O5
• Molecular Weight: 236.224
• DSSTox Substance ID: DTXSID80501227
• Wikidata: Q82353457
• Mol file: 4698-21-9.mol

Synonyms:4698-21-9;3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid;2-Propynoic acid, 3-(3,4,5-trimethoxyphenyl)-;SCHEMBL4640416;DTXSID80501227;JCJHIQYGYVUQEQ-UHFFFAOYSA-N;3,4,5-trimethoxyphenylpropiolic acid;3,4,5-trimethoxyphenylpropynoic acid;AKOS013860531

Chemical Property of 3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 236.06847348
• Heavy Atom Count: 17
• Complexity: 312

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C#CC(=O)O

Technology Process of 3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic acid

There total 14 articles about 3-(3,4,5-Trimethoxyphenyl)prop-2-ynoic 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: 98.0%

methyl 3-(3,4,5-trimethoxyphenyl)-propiolate (71616-33-6) → 3-(3,4,5-trimethoxyphenyl)propiolic acid (4698-21-9)

Guidance literature:

methyl 3-(3,4,5-trimethoxyphenyl)-propiolate; With lithium hydroxide monohydrate; In tetrahydrofuran; methanol; water; at 20 ℃;

With hydrogenchloride; In water; ethyl acetate; at 0 ℃; for 1h; pH=4;

DOI:10.1016/j.ejmech.2010.09.003

Reference yield: 88.0%

carbon dioxide (124-38-9,18923-20-1) + 1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene (77295-62-6) → 3-(3,4,5-trimethoxyphenyl)propiolic acid (4698-21-9)

Guidance literature:

1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.joc.7b02957

Reference yield: 74.0%

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) + Propiolic acid (471-25-0) → 3-(3,4,5-trimethoxyphenyl)propiolic acid (4698-21-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 35 ℃; for 24h;

DOI:10.1002/ejoc.201201606

upstream raw materials:

2,3-Dibrom-3-<3,4,5-trimethoxy-phenyl>-propionsaeure-methylester

ethyl 2,3-dibromo-3-(3,4,5-trimethoxyphenyl)propionate

(E)-3,4,5-trimethoxy-cinnamic acid

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate

Downstream raw materials:

2-Methoxy-3,4-methylenedioxycinnamyl 3',4',5'-trimethoxyphenylpropiolate

3-methoxy-4,5-methylenedioxycinnamyl 3',4',5'-trimethoxyphenylpropiolate

(3,4,5-Trimethoxy-phenyl)-propynoic acid (E)-3-(1-benzenesulfonyl-1H-indol-2-yl)-allyl ester

(Z)3,4,5-trimethoxycinnamic acid