104682-97-5

Basic information

• Product Name: 2-Propenoic acid, 3-(1H-indol-7-yl)-, Methyl ester
• Synonyms: 2-Propenoic acid, 3-(1H-indol-7-yl)-, Methyl ester;(E)-Methyl 3-(1H-indol-7-yl)acrylate;3-(1H-indol-7-yl)-2-propenoic acid Methyl ester;Methyl (2E)-3-(1H-indol-7-yl)prop-2-enoate;4-(1H-indol-7-yl)-1-Methoxybut-3-en-2-one;Methyl 3-(1H-indol-7-yl)acrylate
• CAS NO: 104682-97-5
• Molecular Formula: C₁₂H₁₁NO₂
• Molecular Weight: 201.22124
• Mol File: 104682-97-5.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propenoic acid, 3-(1H-indol-7-yl)-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenoic acid, 3-(1H-indol-7-yl)-, Methyl ester(104682-97-5)
• EPA Substance Registry System: 2-Propenoic acid, 3-(1H-indol-7-yl)-, Methyl ester(104682-97-5)

Safety Data

• Hazardous Substances Data: 104682-97-5(Hazardous Substances Data)

Usage

General Description

2-Propenoic acid, 3-(1H-indol-7-yl)-, methyl ester, also known as Methyl indole-3-acrylate, is a chemical compound with the molecular formula C12H11NO2. It is a colorless to yellow liquid with a fruity odor, commonly used in the production of perfumes and fragrances due to its pleasant scent. It is also utilized in the pharmaceutical industry as a precursor to various indole derivatives, which have a wide range of biological and pharmacological activities. Additionally, this compound has potential applications in the field of organic synthesis for the preparation of diverse chemical products. However, it is important to handle this chemical with caution as it may have harmful effects if mishandled or exposed inappropriately.

Upstream product

• 1074-88-0 1H-indole-7-carbaldehyde 
• 5927-18-4 trimethyl phosphonoacetate 
• 120-72-9 indole 
• 292638-85-8 acrylic acid methyl ester 
• 53406-38-5 1H-indol-1-amine 
• 51417-51-7 7-bromo-1H-indole 
• 93247-78-0 methyl 1H-indole-7-carboxylate 
• 5471-82-9 methyl 3-methyl-2-nitrobenzoate 
• 1074-87-9 indole-7-methanol 
• 104682-96-4 2,3-dihydro-7-iodoindole 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1314947-18-6 3-(1H-indol-7-yl)-prop-2-en-1-ol 
• 288371-43-7 (E)-3-(1H-indol-7-yl)acrylic acid 
• 915377-39-8 methyl 3-(1H-indol-7-yl)propanoate 
• 408356-04-7 7-(3-hydroxypropyl)indole 
• 890120-41-9 5-[7-(3-acetoxy-propyl)-1H-indole-3-carbonyl]-4-hydroxy-3-phenyl-furan-2-carboxylic acid methyl ester 
• 890120-39-5 5-[7-(3-acetoxy-propyl)-1H-indole-3-carbonyl]-4-methoxy-3-phenyl-furan-2-carboxylic acid methyl ester 
• 915377-53-6 4-methoxy-5-[7-(2-methoxycarbonyl-ethyl)-1H-indole-3-carbonyl]-3-phenyl-furan-2-carboxylic acid methyl ester 
• 915377-55-8 4-hydroxy-5-[7-(2-methoxycarbonyl-ethyl)-1H-indole-3-carbonyl]-3-phenyl-furan-2-carboxylic acid methyl ester 

Relevant articles and documents

A Modified ToxT Inhibitor Reduces Vibrio cholerae Virulence in Vivo

We have previously designed and synthesized small-molecule inhibitors that reduce Vibrio cholerae virulence in vitro by targeting the transcription factor ToxT. Here we report the synthesis and biological activity of derivatives of our previous bicyclic, fatty acid-like inhibitors. All of the synthesized derivatives show antivirulence activity in vitro. For the most potent compounds, a concentration of 5 μM completely inhibited ToxT-mediated tcpA expression as measured in the β-galactosidase assay. One indole compound, 3-(1-butyl-1H-indol-7-yl)propanoic acid (8), was also effective at inhibiting intestinal colonization in the infant mouse. These modified compounds may serve as good candidates for further anti-cholera drug development.

Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group

An efficient rhodium-catalyzed method for C-H olefination at the C7 position of indoles has been developed. The N-imino directing group was shown to be crucial for high regioselectivity and reactivity of the metal catalyst. The utility of this protocol was further demonstrated through a concise, four-step synthesis of pyroquilon from indole.

Sulfur-Directed C7-Selective Alkenylation of Indoles under Rhodium Catalysis

Regioselective direct functionalization of an indole benzenoid fragment has been a significant challenge because of its inherently lower reactivity. In this report, we introduce a Rh-catalyzed C7-selective alkenylation of indole derivatives using a new sulfur directing group N-SCy. A notable feature of this system is that the directing group is readily installed to the indoles and easily removed after the catalysis under mild conditions.