3-Indoleacrylic acid

Base Information

• Chemical Name: 3-Indoleacrylic acid
• CAS No.: 29953-71-7
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.198
• Hs Code.: 2933998090
• European Community (EC) Number: 214-872-7,621-733-8
• UNII: 83X500J040
• DSSTox Substance ID: DTXSID90184060
• Nikkaji Number: J36.994B,J363.762J
• Wikidata: Q27225487
• Metabolomics Workbench ID: 71804
• ChEMBL ID: CHEMBL445966
• Mol file: 29953-71-7.mol

Synonyms:3-indolylacrylic acid;indole acrylic acid;indoleacrylic acid;indoleacrylic acid, (E)-isomer;indoleacrylic acid, sodium salt

Chemical Property of 3-Indoleacrylic acid

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Vapor Pressure: 1.18E-07mmHg at 25°C
• Melting Point: 185 °C (dec.)(lit.)
• Refractive Index: 1.727
• Boiling Point: 432.8 °C at 760 mmHg
• PKA: 4.59±0.10(Predicted)
• Flash Point: 215.6 °C
• PSA: 53.09000
• Density: 1.361 g/cm³
• LogP: 2.26570
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: freely soluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 187.063328530
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-Indole-3-acrylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C=CC(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)/C=C/C(=O)O
• Uses: trans-3-Indoleacrylic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals.

Technology Process of 3-Indoleacrylic acid

There total 16 articles about 3-Indoleacrylic 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: 91.0%

Indole-3-carboxaldehyde (487-89-8,1228547-52-1) + malonic acid (141-82-2) → trans-3-indole-acrylic acid (1204-06-4,29953-71-7)

Guidance literature:

With piperidine; pyridine; at 40 ℃; for 5h;

DOI:10.1016/j.bmc.2014.04.027

Reference yield: 80.0%

3-(1H-indol-3-yl)-acrylic acid ethyl ester (110110-37-7) → trans-3-indole-acrylic acid (1204-06-4,29953-71-7)

Guidance literature:

With sodium hydroxide; In ethanol; water; for 3h; Heating;

Reference yield:

(E)-methyl 3-(1-acetyl-1H-indol-3-yl)acrylate (19626-93-8) → trans-3-indole-acrylic acid (1204-06-4,29953-71-7)

Guidance literature:

With sodium hydroxide; water; In ethanol; at 70 ℃; for 8h;

upstream raw materials:

Indole-3-carboxaldehyde

malonic acid

1-acetyl-3-indolylcarbaldehyde

Indole-3-propionic acid

Downstream raw materials:

cis-3-indole acrylic acid

Refernces

• 1、 Hawash, Mohammed,Kahraman, Deniz Cansen,Cetin-Atalay, Rengul,Baytas, Sultan Nacak. "Induction of Apoptosis in Hepatocellular Carcinoma Cell Lines by Novel Indolylacrylamide Derivatives: Synthesis and Biological Evaluation". . . Retrieved 2021/04/28.
• 2、 Xu, Yun-Yun,Li, Si-Ning,Yu, Gao-Jian,Hu, Qing-Hua,Li, Huan-Qiu. "Discovery of novel 4-anilinoquinazoline derivatives as potent inhibitors of epidermal growth factor receptor with antitumor activity". . p. 6084 - 6091. Retrieved 2013/09/23.