1218790-31-8 | 1-BOC-7-Chloroindole-3-boronic acid, pinacol ester

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$137.00	$96.00
1g	97%	in stock	$330.00	$231.00
5g	97%	in stock	$1,131.00	$792.00

Description

• Catalog Number: AA54552
• Chemical Name: 1-BOC-7-Chloroindole-3-boronic acid, pinacol ester
• CAS Number: 1218790-31-8
• Molecular Formula: C19H25BClNO4
• Molecular Weight: 377.6701
• MDL Number: MFCD15143613
• SMILES: Clc1cccc2c1n(cc2B1OC(C(O1)(C)C)(C)C)C(=O)OC(C)(C)C

Computed Properties

• Complexity: 546
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 26
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3

Upstream Synthesis Route

Tert-Butyl 7-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate is a versatile compound that finds application in chemical synthesis due to its unique structural features and reactivity. This compound serves as a valuable building block in organic chemistry, particularly in the synthesis of complex molecules and pharmaceutical intermediates.One key application of tert-Butyl 7-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate is in cross-coupling reactions, such as Suzuki-Miyaura coupling. The presence of the boron functional group in the molecule allows for efficient and selective C-C bond formation with various aryl or vinyl halides, enabling the synthesis of biaryl compounds and other structurally diverse products. Additionally, the chloro substituent on the 7-position of the indole ring provides a site for further functionalization through nucleophilic substitution or transition metal-catalyzed reactions.Moreover, the tert-butyl ester group on the carboxylate moiety offers protection to the indole nitrogen and carboxylic acid functionalities, allowing for controlled manipulation of the molecule during synthetic transformations. This protective group can be selectively removed under mild conditions to reveal the reactive sites for subsequent chemical modifications.In summary, tert-Butyl 7-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate is a valuable reagent in chemical synthesis, enabling efficient construction of complex molecular frameworks and facilitating the development of novel compounds with potential applications in medicinal chemistry and materials science.