551-41-7

Basic information

• Product Name: tert-butyl 1H-indol-3-ylacetate
• CAS NO: 551-41-7
• Molecular Formula: C₁₄H₁₇NO₂
• Molecular Weight: 231.2903
• Mol File: 551-41-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 365.4°C at 760 mmHg
• Flash Point: 174.8°C
• Density: 1.132g/cm³
• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.583
• CAS DataBase Reference: tert-butyl 1H-indol-3-ylacetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 1H-indol-3-ylacetate(551-41-7)
• EPA Substance Registry System: tert-butyl 1H-indol-3-ylacetate(551-41-7)

Safety Data

• Hazardous Substances Data: 551-41-7(Hazardous Substances Data)

Usage

General Description

Tert-butyl 1H-indol-3-ylacetate is a chemical compound with the molecular formula C15H19NO2. It is an ester derivative of indole and is composed of a tert-butyl group attached to the nitrogen atom of the indole ring, as well as an acetate group attached to the carbon in position 3 of the indole ring. tert-butyl 1H-indol-3-ylacetate is often used in the synthesis of various pharmaceuticals and organic molecules, as it has potential pharmacological and biological activities. Tert-butyl 1H-indol-3-ylacetate can also act as a precursor for the preparation of other organic compounds through various chemical reactions and transformations.

Upstream product

• 120-72-9 indole 
• 540-88-5 acetic acid tert-butyl ester 
• 87-51-4 indole-3-acetic acid 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 

Relevant articles and documents

Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer

Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec

Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.

Direct coupling of indoles with carbonyl compounds: Short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families

The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and hapali