| Identification | More | [Name]
3-Indoleacetamide | [CAS]
879-37-8 | [Synonyms]
2-(1H-INDOL-3-YL)ACETAMIDE
3-INDOLEACETAMIDE
INDOLE-3-ACETAMIDE
INDOLEACETAMIDE
1H-Indole-3-acetamide
1-Indole-3-acetamide
Indol-3-ylacetamide
3-acetamidoindole
ACETAMIDOINDOZE
3-Indoleace
Indole-3-acetamide ,98%
2-(1H-Indole-3-yl)acetamide
3-(2-Oxo-2-aminoethyl)-1H-indole | [EINECS(EC#)]
212-904-4 | [Molecular Formula]
C10H10N2O | [MDL Number]
MFCD00005641 | [Molecular Weight]
174.2 | [MOL File]
879-37-8.mol |
| Chemical Properties | Back Directory | [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 | [Detection Methods]
HPLC,NMR | [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) |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [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 |
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