374818-66-3

Basic information

• Product Name: 5-Iodo-1H-indole, N-BOC protected
• Synonyms: 5-Iodo-1H-indole, N-BOC protected;tert-Butyl 5-iodo-1H-indole-1-carboxylate;5-Iodo-1H-indole, N-BOC protected 97%;1-BOC-5-iodoindole;tert-Butyl 5-iodo-1H-indole-1-carboxylate, 1-(tert-Butoxycarbonyl)-5-iodo-1H-indole;1H-Indole-1-carboxylic acid, 5-iodo-, 1,1-diMethylethyl ester;5-Iodo-1H-indole,N-BOCprotected97%
• CAS NO: 374818-66-3
• Molecular Formula: C₁₃H₁₄INO₂
• Molecular Weight: 343.16023
• Product Categories: blocks;IndolesOxindoles;Iodides
• Mol File: 374818-66-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 388.372 °C at 760 mmHg
• Flash Point: 188.681 °C
• Appearance: /
• Density: 1.56 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Iodo-1H-indole, N-BOC protected(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-1H-indole, N-BOC protected(374818-66-3)
• EPA Substance Registry System: 5-Iodo-1H-indole, N-BOC protected(374818-66-3)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 374818-66-3(Hazardous Substances Data)

Usage

General Description

5-Iodo-1H-indole, N-BOC protected, is a chemical compound with the molecular formula C16H15INO3. It is a derivative of 1H-indole that has a BOC (tert-butyloxycarbonyl) group protecting the amine group. 5-Iodo-1H-indole, N-BOC protected is useful in organic synthesis as it can be deprotected to reveal the free amine, allowing for further functionalization. It is often used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other bioactive compounds. 5-Iodo-1H-indole, N-BOC protected, has potential applications in medicinal chemistry and drug discovery due to its versatile reactivity and ability to introduce specific functionalities into molecules.

InChI:InChI=1/C13H14INO2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,1-3H3

Upstream product

• 16066-91-4 5-iodo-1H-indole 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 889108-48-9 5-ethynyl-1H-indole 
• 913388-48-4 5-(4-methyl-piperazin-1-yl)-indole-1-carboxylic acid tert-butyl ester 
• 351500-12-4 tert-butyl 5-(trifluoromethyl)-1H-indole-1-carboxylate 
• 777061-36-6 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 
• 943772-67-6 5-[4-(4-bromo-phenylcarbamoyl)-2-nitro-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester 
• 943772-68-7 5-[2-amino-4-(4-bromo-phenylcarbamoyl)-phenylsulfanyl]-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

One-pot access to L-5,6-dihalotryptophans and L-alknyltryptophans using tryptophan synthase

We report, for the first time, the use of tryptophan synthase in the generation of L-dihalotryptophans and L-alkynyltryptophans. These previously unpublished compounds will be useful tools in the generation of probes for chemical biology, in biosynthetic diversification and as convenient building blocks for synthesis.

Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2-H Functionalizations

Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.

Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides

By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.