Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate

Base Information

• Chemical Name: Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate
• CAS No.: 873208-18-5
• Molecular Formula: C₉H₁₀O₂S
• Molecular Weight: 182.243
• DSSTox Substance ID: DTXSID90381294
• Mol file: 873208-18-5.mol

Synonyms:Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate;873208-18-5;DTXSID90381294;FT-0772635;METHYL3-(3-METHYL-2-THIENYL)ACRYLATE

Chemical Property of Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate

Chemical Property:

• PSA: 54.54000
• LogP: 2.24270
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 182.04015073
• Heavy Atom Count: 12
• Complexity: 189

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=C1)C=CC(=O)OC

Technology Process of Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate

There total 4 articles about Methyl 3-(3-methylthiophen-2-yl)prop-2-enoate 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: 80.0%

3-Methylthiophene (616-44-4,84928-92-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl trans-β-(3-methyl-2-thienyl)acrylate (873208-18-5)

Guidance literature:

With tetrafluoroboric acid diethyl ether; sodium 3-(methylthio)propane-1-sulfonate; palladium diacetate; acetic acid; hydroquinone; In tetrahydrofuran; at 40 ℃; for 18h;

DOI:10.1021/jacs.7b03887

Reference yield: 77.0%

2-bromo-3-methylthiophene (14282-76-9) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl trans-β-(3-methyl-2-thienyl)acrylate (873208-18-5)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); N-Methyldicyclohexylamine; 4,4'-di-tert-butylbiphenyl; tetrabutyl-ammonium chloride; In N,N-dimethyl acetamide; at 80 ℃; for 24h; Glovebox;

DOI:10.1021/op300364p

Reference yield: 13.0%

3-Methylthiophene (616-44-4,84928-92-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → C9H10O2S + dimethyl 3,3'-(3-methylthiophene-2,5-diyl)(2E,2'E)diacrylate + methyl trans-β-(3-methyl-2-thienyl)acrylate (873208-18-5)

Guidance literature:

With 3-methyl-2-(phenylthio)butanoic acid; silver(I) acetate; palladium diacetate; In ethyl acetate; at 60 ℃; for 6h; Sealed tube;

DOI:10.1002/ejoc.201900077

upstream raw materials:

2-bromo-3-methylthiophene

acrylic acid methyl ester

3-Methylthiophene

Refernces

• 1、 Gorsline, Bradley J.,Wang, Long,Ren, Peng,Carrow, Brad P.. "C-H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands". supporting information. p. 9605 - 9614. Retrieved 2017/07/24.