879-37-8

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 NO: 879-37-8
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• EINECS: 212-904-4
• Product Categories: Indoles and derivatives;Pyrroles & Indoles;Indole;Indoles;Simple Indoles;Pyrroles & Indoles;Building Blocks;Heterocyclic Building Blocks;Heterocycle-Indole series
• Mol File: 879-37-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 148-150 °C(lit.)
• Boiling Point: 469.7 °C at 760 mmHg
• Flash Point: 237.8 °C
• Appearance: /
• Density: 1.285 g/cm³
• Vapor Pressure: 5.4E-09mmHg at 25°C
• Refractive Index: 1.687
• Storage Temp.: -20°C
• Solubility: DMSO (Slightly)
• PKA: 16.37±0.40(Predicted)
• CAS DataBase Reference: 3-Indoleacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Indoleacetamide(879-37-8)
• EPA Substance Registry System: 3-Indoleacetamide(879-37-8)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• Hazardous Substances Data: 879-37-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Indole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid.

Definition

ChEBI: A member of the class of acetamides 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).

General Description

Indole-3-acetamide is an auxin precursor.

InChI:InChI=1/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

Upstream product

• 239127-19-6 ethyl 3-indolylmethyl sulfide 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 50720-05-3 indolyl acetyl chloride 
• 1912-33-0 Indole-3-acetic acid methyl ester 
• 778-82-5 ethyl 3-indoleacetate 
• 771-51-7 indole-3-acetonitrile 
• 18443-04-4 3-indolylacetic acid ethyl imido ester hydrochloride 
• 63853-74-7 5-methoxypyrrolidin-2-one 
• 100-63-0 phenylhydrazine 
• 392-12-1 Indole-3-pyruvic acid 
• 7664-41-7 ammonia 
• 67-63-0 isopropyl alcohol 
• 73-22-3 L-Tryptophan 
• 5448-47-5 1H-indol-3-acetohydrazide 

Downstream Products

• 61-54-1 tryptamine 
• 87-51-4 indole-3-acetic acid 
• 150114-41-3 1-methylindole-3-acetamide 
• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 219817-92-2 3-<4-(1-(methoxymethyl)-1H-2-(phenylthio)imidazol-5-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl>indole 
• 259752-97-1 16-phenylthiodidemnimide C 
• 203719-72-6 2-[1-(2-{3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]ethanamide 
• 1026294-20-1 3-{1-[3-(2-hydroxyethoxy)-4-(phenylmethoxy)butyl]indol-3-yl}-4-(indol-3-yl)-3-pyrroline-2,5-dione 
• 336883-76-2 6,7,10,11-tetrahydro-9-[(phenylmethoxy)methyl]-9H,18H-5,21:12,17-dimethenodibenzo[e,k]pyrrolo[3,4-h][1,4,13]oxadiazacyclohexadecine-18,20(19H)-dione 
• 175601-94-2 2-(2,3-dihydro-1H-indol-3-yl)acetamide 
• 257874-86-5 2-(1-{3-[(tert-butyl)dimethylsilanyloxy]propyl}-1H-indol-3-yl)acetamide 
• 257876-71-4 2-{1-[(R)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide 
• 257875-28-8 2-{1-[(S)-2-(tert-butyldiphenylsilyloxymethyl)-4,4-diethoxybutyl]-1H-indol-3-yl}acetamide 
• 918327-55-6 2-(1-{2-[1-(1,4-dioxa-spiro[4.5]dec-2-yl)-3-trityloxy-propoxy]-ethyl}-1H-indol-3-yl)-acetamide 

Relevant articles and documents

Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex

Catalytic aerobic oxidation of primary amines to the amides, using the precatalyst [Ru(COD)(L1)Br2] (1) bearing an annulated π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand L1, is disclosed. This catalytic protocol is distinguished by its high activity and selectivity, wide substrate scope and modest reaction conditions. A variety of primary amines, RCH2NH2 (R = aliphatic, aromatic and heteroaromatic), are converted to the corresponding amides using ambient air as an oxidant in the presence of a sub-stoichiometric amount of KOtBu in tBuOH. A set of control experiments, Hammett relationships, kinetic studies and DFT calculations are undertaken to divulge mechanistic details of the amine oxidation using 1. The catalytic reaction involves abstraction of two amine protons and two benzylic hydrogen atoms of the metal-bound primary amine by the oxo and hydroxo ligands, respectively. A β-hydride transfer step for the benzylic C-H bond cleavage is not supported by Hammett studies. The nitrile generated by the catalytic oxidation undergoes hydration to afford the amide as the final product. This journal is

Molecular-docking-guided design and synthesis of new IAA-tacrine hybrids as multifunctional AChE/BChE inhibitors

A series of new indole-3-acetic acid (IAA)-tacrine hybrids as dual acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) inhibitors were designed and prepared based on the molecular docking mode of AChE with an IAA derivative (1a), a moderate AChE inhibitor identified by screening our compound library for anti-Alzheimer's disease (AD) drug leads. The enzyme assay results revealed that some hybrids, e.g. 5d and 5e, displayed potent dual in vitro inhibitory activities against AChE/BChE with IC50 values in low nanomolar range. Molecular modeling studies in tandem with kinetic analysis suggest that these hybrids target both catalytic active site and peripheral anionic site of cholinesterase (ChE). Molecular dynamic simulations and Molecular Mechanics/Poisson-Boltzmann Surface Area (MM-PBSA) calculations indicate that 5e has more potent binding affinity than hit 1a, which may explain the stronger inhibitory effect of 5e on AChE. Furthermore, their predicted pharmacokinetic properties and in vitro influences on mouse brain neural network electrical activity were discussed. Taken together, compound 5e can be highlighted as a lead compound worthy of further optimization for designing new anti-AD drugs.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.