3-(Methylthio)acrylic acid, (E)-

Base Information

• Chemical Name: 3-(Methylthio)acrylic acid, (E)-
• CAS No.: 26398-93-6
• Molecular Formula: C4H6 O2 S
• Molecular Weight: 118.15
• UNII: 9C2XEZ8RWS
• DSSTox Substance ID: DTXSID901290437
• Nikkaji Number: J175.466A,J175.467J
• Wikidata: Q77373922
• Metabolomics Workbench ID: 113538
• Mol file: 26398-93-6.mol

Synonyms:3-methylthioacrylic acid

Chemical Property of 3-(Methylthio)acrylic acid, (E)-

Chemical Property:

• Vapor Pressure: 0.00897mmHg at 25°C
• Boiling Point: 246.1°C at 760 mmHg
• Flash Point: 102.6°C
• PSA: 62.60000
• Density: 1.22g/cm³
• LogP: 0.94770
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 118.00885060
• Heavy Atom Count: 7
• Complexity: 87.7

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC=CC(=O)O
• Isomeric SMILES: CS/C=C/C(=O)O

Technology Process of 3-(Methylthio)acrylic acid, (E)-

There total 8 articles about 3-(Methylthio)acrylic acid, (E)- 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%

methylthiol (74-93-1) + Propiolic acid (471-25-0) → (E)-β-methylthiopropenoic acid (26398-93-6,26995-94-8) + (Z)-β-methylthiopropenoic acid (70424-09-8,26995-94-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; 1.) 85 deg C, 60 atm (sealed tube), 12 h; 2.) xylene, reflux, 24 h;

DOI:10.1016/S0040-4020(01)80647-5

Reference yield: 39.0%

Propiolic acid (471-25-0) + sodium thiomethoxide (5188-07-8) → (E)-β-methylthiopropenoic acid (26398-93-6,26995-94-8)

Guidance literature:

Propiolic acid; sodium thiomethoxide; for 0.25h;

In methanol; for 15h;

DOI:10.1021/acs.joc.8b01609

Reference yield: 31.0%

(Z)-β-methylthiopropenoic acid (70424-09-8,26995-94-8) → (E)-β-methylthiopropenoic acid (26398-93-6,26995-94-8)

Guidance literature:

With toluene-4-sulfonic acid; In xylene; for 9h;

upstream raw materials:

(Z)-β-methylthiopropenoic acid

methylthiol

Propiolic acid

3c-thiocyanato-acrylic acid

Downstream raw materials:

N-(p-hydroxyphenethyl)-(E)-3-(methylthio)-propenamide

(2Z,4E,11E)-Trideca-2,4,11-trienoic acid (S)-3-(4-methoxy-benzyloxy)-2-((E)-3-methylsulfanyl-acryloyloxy)-propyl ester

Refernces

• 1、 Fuse, Shinichiro,Hayashi, Yoshihiro,Kawauchi, Susumu,Nakamura, Hiroyuki,Otake, Yuma,Shibata, Yusuke. "N-Methylated Peptide Synthesis via Generation of an Acyl N-Methylimidazolium Cation Accelerated by a Br?nsted Acid". supporting information. p. 12925 - 12930. Retrieved 2020/06/04.
• 2、 Moon, Jong Taik,Ha, Sung Hoon,Lee, So Hyung,Kwon, Tae Hui,Oh, Chun Rim,Kim, Young Deuk,Kim, Jungahn,Choo, Dong Joon,Lee, Jae Yeol. "Total synthesis and biological evaluation of methylgerambullone". scheme or table. p. 52 - 55. Retrieved 2010/04/24.