21909-52-4

Basic information

• Product Name: (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE
• Synonyms: (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE;5-METHYLINDOLE-3-ACETIC ACID HYDRAZIDE
• CAS NO: 21909-52-4
• Molecular Formula: C11H13N3O
• Molecular Weight: 203.24
• Mol File: 21909-52-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 516.8 °C at 760 mmHg
• Flash Point: 266.4 °C
• Appearance: /
• Density: 1.265 g/cm³
• Vapor Pressure: 8.66E-11mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE(21909-52-4)
• EPA Substance Registry System: (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE(21909-52-4)

Safety Data

• Hazardous Substances Data: 21909-52-4(Hazardous Substances Data)

Usage

General Description

(5-Methyl-1H-indol-3-yl)-acetic acid hydrazide, also known as 5-Methylindole-3-acetic acid hydrazide, is a chemical compound that is commonly used in the pharmaceutical industry. It is a hydrazide derivative of 5-methylindole-3-acetic acid, which is a synthetic auxin used in the field of plant growth regulators. (5-METHYL-1H-INDOL-3-YL)-ACETIC ACID HYDRAZIDE has been found to have potential biological activities, such as anti-inflammatory and neuroprotective effects, making it a valuable molecule for medicinal research. Additionally, it has also demonstrated potential as a building block for the synthesis of other biologically active compounds, further adding to its significance in chemical and pharmaceutical research.

InChI:InChI=1/C11H13N3O/c1-7-2-3-10-9(4-7)8(6-13-10)5-11(15)14-12/h2-4,6,13H,5,12H2,1H3,(H,14,15)

Upstream product

• 1337870-84-4 (5-methyl-indol-3-yl)-acetic acid methyl ester 

Relevant articles and documents

Synthesis of 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their protective activity against oxidative stress

A small library of 2-[(1H-indol-3-yl)methyl]-5-(alkylthio)-1,3,4-oxadiazoles was prepared, starting from indole-3-acetic acid methyl ester and its 5-methyl-substituted derivative. The synthetic route involved the formation of intermediate hydrazides, their condensation with carbon disulfide, and intramolecular cyclization to corresponding 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones. The latter were then S-alkylated, and in case of ester derivatives, they were further hydrolyzed into corresponding carboxylic acids. All 5-[(1H-indol-3-yl)methyl]-1,3,4-oxadiazole-2(3H)-thiones and their S-alkylated derivatives were then screened for their protective effects in vitro and in vivo. Methyl substitution on the indole ring and propyl, butyl, or benzyl substitution on sulfhydryl group-possessing compounds were revealed to protect Friedreich's ataxia fibroblasts against the effects of glutathione depletion induced by the γ-glutamylcysteine synthetase inhibitor, buthionine sulfoximine. Two of the active compounds also reproducibly increased the survival of Caenorhabditis elegans exposed to juglone-induced oxidative stress.