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)

form 

Solid

pka

16.37±0.40(Predicted)

color 

White to Off-White

InChI

InChI=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)

InChIKey

ZOAMBXDOGPRZLP-UHFFFAOYSA-N

SMILES

N1C2=C(C=CC=C2)C(CC(N)=O)=C1

CAS DataBase Reference

879-37-8(CAS DataBase Reference)

NIST Chemistry Reference

3-Indoleacetamide(879-37-8)

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

3-Indoleacetamide Usage And Synthesis

Chemical Properties

White to Orange to Green powder to crystal

Uses

Indole-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

Definition

ChEBI: 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 Description

Indole-3-acetamide is an auxin precursor.

Biological Activity

Indole-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

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(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