129822-46-4

Basic information

• Product Name: N-(BOC)-4-CHLOROINDOLE
• Synonyms: N-(BOC)-4-CHLOROINDOLE;1-BOC-4-Chloroindole;tert-Butyl 4-chloro-1H-indole-1-carboxylate
• CAS NO: 129822-46-4
• Molecular Formula: C₁₃H₁₄ClNO₂
• Molecular Weight: 251.70876
• Mol File: 129822-46-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 349.9°C at 760 mmHg
• Flash Point: 165.4°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 4.55E-05mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Room temperature.
• CAS DataBase Reference: N-(BOC)-4-CHLOROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(BOC)-4-CHLOROINDOLE(129822-46-4)
• EPA Substance Registry System: N-(BOC)-4-CHLOROINDOLE(129822-46-4)

Safety Data

• Hazardous Substances Data: 129822-46-4(Hazardous Substances Data)

Usage

General Description

N-(BOC)-4-CHLOROINDOLE is a chemical compound that consists of a 4-chloroindole molecule with a BOC (tert-butoxycarbonyl) protecting group attached to the nitrogen atom. The BOC group is commonly used in organic synthesis to protect amine functional groups from unwanted reactions. The 4-chloroindole moiety is a derivative of the heterocyclic compound indole and contains a chlorine atom at the 4-position. N-(BOC)-4-CHLOROINDOLE has potential applications in organic chemistry, medicinal chemistry, and pharmaceutical research, due to the reactivity of the indole moiety and the ability to selectively remove the BOC protective group for further functionalization. The 4-chloroindole structure can also influence the physical and biological properties of compounds it is incorporated into, making it a valuable building block in the synthesis of new chemical entities.

InChI:InChI=1/C13H14ClNO2/c1-13(2,3)17-12(16)15-8-7-9-10(14)5-4-6-11(9)15/h4-8H,1-3H3

Upstream product

• 138343-81-4 4-Chloro-2-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 25235-85-2 4-chloro-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 87-60-5 3-chloro-2-methylbenzenamine 
• 129822-39-5 N-(tert-butoxycarbonyl)-2-amino-6-chlorotoluene 
• 4248-19-5 tert-butyl carbazate 
• 1243601-90-2 1-bromo-2-[(E)-2-bromovinyl]-3-chlorobenzene 

Downstream Products

• 475102-11-5 [1-(tert-butoxycarbonyl)-4-chloro-1H-indol-2-yl]boronic acid 
• 1443151-93-6 tert-butyl 4-chloro-2-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,2-triazin-2-yl)-1H-indole-1-carboxylate 
• 1443151-42-5 4-(4-chloro-1H-indol-2-yl)-N-[2-(4-fluorophenyl)ethyl]-6-methoxy-1,3,5-triazin-2-amine 

Relevant articles and documents

A non-cryogenic method for the preparation of 2-(indolyl) borates, silanes, and silanols

2-Indolyl borates are prepared via addition of LDA to a mixture of N-Bo-indole and triisopropyl borate at 0-5 °C. Following acidic hydrolysis, the boronic acids are isolated by crystallization in good to excellent yield (73-99%). The method is quite general, tolerating a wide range of functional groups, and also provides access to 2-silyl derivatives (80-91%).

1,3,5-TRIAZINE-2-AMINE DERIVATIVES, PREPARATION THEREOF AND DIAGNOSTIC AND THERAPEUTIC USE THEREOF

The present invention relates to compounds corresponding to formula (I) in which: - R1 represents a substituted phenyl; - R2 represents: - a substituted phenyl; - a heteroaromatic group, the said group being unsubstituted or substituted one or more times; - R3 represents a group Alk; - R4 represents a hydrogen atom or a (C1-C4)alkyl; - R5 represents a hydrogen atom, a (C3-C6)cycloalkyl or a (C1-C4)alkyl-O-Alk; - or alternatively R4 and R5, together with the nitrogen atom to which they are attached, constitute a heterocyclic radical chosen from: azetidin-1-yl, pyrrolidin-1-yl, piperid-1-yl, morpholin-4-yl; - R6 represents a group -COOAlk, a group -CONH2 or a group -NHSO2 Alk; - Alk represents a (C1-C4)alkyl, which is unsubstituted or substituted one or more times with a halogen atom; in the form of the base or of an acid-addition salt. Preparation process and diagnostic and therapeutic use

Palladium catalyzed tandem alkenyl- and aryl-C-N bond formation: A cascade N-annulation route to 4-, 5-, 6- and 7-chloroindoles

A series of trihalogenated alkenylbenzenes undergo consecutive palladium catalyzed inter- and intramolecular amination reactions to deliver a series of 1-functionalized mono-chloroindoles. 4-, 5-, 6- and 7-Chloroindoles can all be prepared; carbamates, anilines and amines can be employed as the N-nucleophile.