32933-86-1

Basic information

• Product Name: 3-(2-chloroethyl)-1H-indole
• Synonyms: 3-(2-chloroethyl)-1H-indole;3-(2-Chloroethyl)indole;(Z)-3-(4-Methyl-2-((2-oxoindolin-3-ylidene)Methyl)-1H-pyrrol-3-yl)propanoic acid
• CAS NO: 32933-86-1
• Molecular Formula: C₁₀H₁₀ClN
• Molecular Weight: 179.6461
• EINECS: 251-300-5
• Mol File: 32933-86-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 342.4°Cat760mmHg
• Flash Point: 191.5°C
• Appearance: /
• Density: 1.229
• Vapor Pressure: 0.00015mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: 3-(2-chloroethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-chloroethyl)-1H-indole(32933-86-1)
• EPA Substance Registry System: 3-(2-chloroethyl)-1H-indole(32933-86-1)

Safety Data

• Hazardous Substances Data: 32933-86-1(Hazardous Substances Data)

Usage

General Description

3-(2-chloroethyl)-1H-indole is a chemical compound with the molecular formula C10H10ClN. It is a synthetic derivative of the indole compound, which is commonly found in various natural products. The compound contains a chlorine atom and an ethyl group attached to the indole ring. 3-(2-chloroethyl)-1H-indole has been studied for its potential biological activities, including its antitumor and cytotoxic effects. It may also be used as an intermediate in the synthesis of other organic compounds. Overall, 3-(2-chloroethyl)-1H-indole is a versatile chemical with potential applications in pharmaceutical and chemical industries.

InChI:InChI=1/C10H10ClN/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2

Upstream product

• 526-55-6 2-(3-indole)-ethanol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 15539-10-3 (+)-vincadifformine 
• 1320327-68-1 methyl 2-(spiro[cyclopropane-1,3'-indoline]-2'-ylidene)acetate 

Relevant articles and documents

Lewis Base Catalysis Enables the Activation of Alcohols by means of Chloroformates as Phosgene Substitutes

Nucleophilic substitutions (SN) are typically promoted by acid chlorides as sacrificial reagents to improve the thermodynamic driving force and lower kinetic barriers. However, the cheapest acid chloride phosgene (COCl2) is a highly toxic gas. Against this background, phenyl chloroformate (PCF) was discovered as inherently safer phosgene substitute for the SN-type formation of C?Cl and C?Br bonds using alcohols. Thereby, application of the Lewis bases 1-formylpyrroldine (FPyr) and diethylcyclopropenone (DEC) as catalysts turned out to be pivotal to shift the chemoselectivity in favor of halo alkane generation. Primary, secondary and tertiary, benzylic, allylic and aliphatic alcohols are appropriate starting materials. A variety of functional groups are tolerated, which includes even acid labile moieties such as tert-butyl esters and acetals. Since the by-product phenol can be isolated, a recycling to PCF with inexpensive phosgene would be feasible on a technical scale. Eventually, a thorough competitive study demonstrated that PCF is indeed superior to phosgene and other substitutes.

METHOD OF CONVERTING ALCOHOL TO HALIDE

The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.

HETEROCYCLIC COMPOUNDS

Indole derivatives of the general formula (I) are disclosed: where R1 is H or an alkyl or alkenyl group, R2 is H, or an alkyl, alkenyl, aryl, aralkyl or cycloalkyl group; R3 is H or an alkyl group; R4 and R5 are independently H or an alkyl or propenyl group or together form an aralkylidene group; and Alk is an optionally substituted alkylene chain; and their physiologically acceptable salts and solutes. These compounds are potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner. Various methods for the production of the compounds are disclosed including a Fischer-indole cyclization process