119668-50-7

Basic information

• Product Name: N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97
• Synonyms: N,N-diethylindole-1-carboxamide;N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97
• CAS NO: 119668-50-7
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.282
• Product Categories: Heterocyclic Compounds
• Mol File: 119668-50-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 140-147 °C/0.8 mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 1.089 g/mL at 25 °C
• Vapor Pressure: 0.00015mmHg at 25°C
• Refractive Index: n20/D 1.575
• CAS DataBase Reference: N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97(CAS DataBase Reference)
• NIST Chemistry Reference: N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97(119668-50-7)
• EPA Substance Registry System: N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97(119668-50-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 119668-50-7(Hazardous Substances Data)

Usage

Description

N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97, also known as Ibogaine, is a naturally occurring indole alkaloid derived from the African shrub Tabernanthe iboga. It possesses psychoactive properties and has been extensively studied for its potential therapeutic applications.
Used in Pharmaceutical Industry:
N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97 is used as a reactant in the preparation of substituted indoles via ortho-metalation and Suzuki-Miyaura cross coupling for the development of novel pharmaceutical compounds with potential therapeutic benefits.
Used in Chemical Synthesis:
N N-DIETHYL-1H-INDOLE-1-CARBOXAMIDE 97 is used as a reactant in the synthesis of various substituted indole derivatives, which can be further utilized in the development of new chemical entities with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C13H16N2O/c1-3-14(4-2)13(16)15-10-9-11-7-5-6-8-12(11)15/h5-10H,3-4H2,1-2H3

Upstream product

• 120-72-9 indole 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 61589-12-6 N-(N',N'-diethylcarbamyl)indoline 
• 110-62-3 pentanal 
• 1239950-36-7 3-iodoindole-1-carboxylic acid diethylamide 
• 100-52-7 benzaldehyde 
• 75-07-0 acetaldehyde 

Downstream Products

• 548775-58-2 2-trimethylsilanyl-indole-1-carboxylic acid diethylamide 
• 933-67-5 7-methyl-1H-indole 
• 1863-21-4 7-(phenyl)-1H-indole 
• 52886-06-3 hippadine 
• 548775-90-2 7-phenyl-indole-1-carboxylic acid diethylamide 
• 137777-60-7 2-(2-Benzyl-1,3-dithian-2-yl)-1-(diethylcarbamoyl)indole 
• 120-72-9 indole 
• 858647-69-5 N,N-diethyl-2-phenyl-1H-indole-1-carboxamide 
• 1335095-78-7 C₁₉H₂₀N₂O 

Relevant articles and documents

Re-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C?H/C?N Bond Cleavage

Described herein are rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C?H/C?N bond cleavage, which provide rapid access to fused-ring pyrroloindolone derivatives. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C?H activation reactions, enabled by the unique catalytic trio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.

C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.

Schwartz Reagents: Methods of In Situ Generation and Use

Embodiments of the invention provide a method of using Schwartz Reagent, Cp2Zr(H)Cl, without accumulating or isolating it. Methods provide mixtures of Cp2ZrCl2, reductants that selectively reduce Cp2ZrCl2, and substrates. After reaction of Cp2ZrCl2 and the reductant, an intermediate reduction product is formed, apparently Schwartz Reagent. The in situ Schwartz Reagent then selectively reduces certain functional groups on the substrate. Substrates include tertiary amides, tertiary benzamides, aryl O-carbamates, and heteroaryl N-carbamates, which are reduced to aldehydes, benzaldehydes, aromatic alcohols, and heteroaromatics, respectively. Compared to prior methods, reagents are inexpensive and stable, reaction times are short, and reaction temperature in certain cases is conveniently room temperature. It has been estimated that using the in situ method described herein instead of synthesized or commercially obtained Schwartz Reagent provides a 50% reduction in cost.