3-Indoleacetamide

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Products Intro: Product Name:3-IndoleacetaMide
CAS:879-37-8
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CAS:879-37-8
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3-Indoleacetamide manufacturers

  • 3-Indoleacetamide
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  • Indole-3-acetamide
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  • 2025-09-25
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Related articles

3-Indoleacetamide Basic information
Product Name:3-Indoleacetamide
Synonyms:INDOLE-3-ACETAMIDE;INDOLEACETAMIDE;2-(1H-INDOL-3-YL)ACETAMIDE;3-INDOLEACETAMIDE;1H-Indole-3-acetamide;1-Indole-3-acetamide;Indol-3-ylacetamide;3-acetamidoindole
CAS:879-37-8
MF:C10H10N2O
MW:174.2
EINECS:212-904-4
Product Categories:Heterocycle-Indole series;Simple Indoles;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Pyrroles & Indoles;Indole;Indoles;Indoles and derivatives
Mol File:879-37-8.mol
3-Indoleacetamide Structure
3-Indoleacetamide Chemical Properties
Melting point 148-150 °C(lit.)
Boiling point 469.7±28.0 °C(Predicted)
density 1.285±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility DMSO (Slightly)
pka16.37±0.40(Predicted)
form Solid
color White to Off-White
InChIInChI=1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)
InChIKeyZOAMBXDOGPRZLP-UHFFFAOYSA-N
SMILESN1C2=C(C=CC=C2)C(CC(N)=O)=C1
CAS DataBase Reference879-37-8(CAS DataBase Reference)
NIST Chemistry Reference3-Indoleacetamide(879-37-8)
Safety Information
Hazard Codes Xi
WGK Germany 3
Hazard Note Irritant
HS Code 29339900
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
3-Indoleacetamide Usage And Synthesis
Chemical PropertiesWhite to Orange to Green powder to crystal
UsesIndole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid.
Reactant for the synthesis of:
PET agent for imaging of protein kinase C
A potential agent against Prion Disease
Protein kinase C (PKC) inhibitor bisindolylmaleimide IV
Glycogen synthase kinase-3 (GSK-3) inhibitors
Inhibitors of CaMKIId
A VEGF inhibitor
JAK3 inhibitors
Inhibitors of NAD+-Dependent Histone Deacetylases
Inhibitors of human adipocyte fatty acid-binding protein
Cyclin-dependent kinase inhibitors
DefinitionChEBI: Indole-3-acetamide is a member of the class of indoles that is acetamide substituted by a 1H-indol-3-yl group at position 2. It is an intermediate in the production of plant hormone indole acetic acid (IAA). It has a role as a fungal metabolite, a bacterial metabolite and a plant metabolite. It is a N-acylammonia, a monocarboxylic acid amide and a member of indoles. It is functionally related to an acetamide.
General DescriptionIndole-3-acetamide is an auxin precursor.
Biological ActivityIndole-3-acetamide is a biosynthesis intermediate of indole-3-acetic acid. Indole-3-acetic acid is the most common natural plant growth hormone of the auxin class.
Synthesis
3-Indoleacetonitrile

771-51-7

3-Indoleacetamide

879-37-8

The general procedure for the synthesis of 3-indoleacetamide from indole-3-acetonitrile was as follows: the reaction was carried out in a 100-mL stainless steel autoclave. Indole-3-acetonitrile (0.10 g, 1.00 mmol) was added to a mixture of ethylenediamine (0.12 g, 2.00 mmol), CoCl2-H2O (0.24 g, 1.00 mmol), and Zn (0.07 g, 1.00 mmol) and the mixture was transferred to the autoclave. For reactions to be performed in solvent, an additional 5 mL of solvent was added. The autoclave was pressurized to 5.00 atm using O2. the reaction mixture was stirred in a preheated 120°C oil bath for 12 hr. Upon completion of the reaction, the mixture was cooled to room temperature and the product was purified by silica gel column chromatography using a solvent mixture of n-hexane and CH2Cl2 (1:1) as eluent to give the final 3-indoleacetamide in 88% yield.

References[1] Tetrahedron, 1989, vol. 45, # 5, p. 1347 - 1354
[2] Research on Chemical Intermediates, 2015, vol. 41, # 8, p. 5071 - 5078
[3] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 5, p. 501 - 506
[4] Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 5, p. 645 - 650
3-Indoleacetamide Preparation Products And Raw materials
Raw materials3-Indoleacetonitrile-->Indole-3-acetic acid-->Cobalt chloride hexahydrate-->Ethylenediamine-->Oxygen-->ZINC
Preparation ProductsTryptophol-->3-Indoleacetonitrile
Tag:3-Indoleacetamide(879-37-8) Related Product Information
2-Cyanoacetamide Indole Chloroacetamide 2-Phenylacetamide Thioacetamide Acetaminophen Acetamide 2-Iodoacetamide N,N-Dimethylacetamide Ethyl indole-3-carboxylate Indole-5-carboxaldehyde Indole-3-carboxaldehyde Indole-4-carboxaldehyde Indole-5-carboxylic acid Indole-4-carboxylic acid Methyl 1H-indole-7-carboxylate Indole-6-boronic acid pinacol ester Indole-3-butyric acid