115377-94-1

Basic information

• Product Name: (2-BOC-AMINOPHENYL)BORONIC ACID
• Synonyms: N-(TERT-BUTOXYCARBONYL)2-AMINO-1-PHENYLBORONIC ACID;AKOS BRN-0240;2-(T-BUTOXYCARBONYLAMINO)PHENYLBORONIC ACID;2-(TERT-BUTOXYCARBONYLAMINO)PHENYLBORONIC ACID;2-(N-BOC-AMINO)PHENYLBORONIC ACID;(2-BOC-AMINOPHENYL)BORONIC ACID;2-Aminobenzeneboronic acid, N-BOC protected;(2-Boronophenyl)carbamicacid
• CAS NO: 115377-94-1
• Molecular Formula: C₁₁H₁₆BNO₄
• Molecular Weight: 237.06
• Product Categories: Amines;blocks;BoronicAcids;Amino;Aryl;Organoborons;Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 115377-94-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 123-125°C
• Appearance: /
• Density: 1.183 g/cm³
• Refractive Index: 1.53
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 8.54±0.53(Predicted)
• CAS DataBase Reference: (2-BOC-AMINOPHENYL)BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2-BOC-AMINOPHENYL)BORONIC ACID(115377-94-1)
• EPA Substance Registry System: (2-BOC-AMINOPHENYL)BORONIC ACID(115377-94-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 115377-94-1(Hazardous Substances Data)

Usage

General Description

(2-BOC-AMINOPHENYL)BORONIC ACID, also known as N-(tert-butoxycarbonyl)aniline-4-boronic acid, is a boronic acid derivative commonly used in organic synthesis. It is a white to off-white solid that is soluble in organic solvents. This chemical is often employed as a building block in the production of pharmaceuticals, agrochemicals, and other fine chemicals. With its boronic acid functionality and protecting group, (2-BOC-AMINOPHENYL)BORONIC ACID has proven to be a valuable tool in the development of new compounds and materials in the field of medicinal chemistry and drug discovery. Its potential application in Suzuki-Miyaura cross-coupling reactions and related transformations makes it a highly sought-after reagent in the research and development of new chemical entities.

InChI:InChI=1/C11H16BNO4/c1-11(2,3)17-10(14)13-9-7-5-4-6-8(9)12(15)16/h4-7,15-16H,1-3H3,(H,13,14)

Upstream product

• 3422-01-3 tert-butyl phenylcarbamate 
• 121-43-7 Trimethyl borate 
• 594-19-4 tert.-butyl lithium 
• 24424-99-5 di-tert-butyl dicarbonate 
• 62-53-3 aniline 
• 5570-18-3 2-aminophenylboronic acid 

Downstream Products

• 1015-89-0 6(5H)-phenanthridinone 
• 232276-04-9 N-(2,6-dichlorobenzoyl)-4-[2-(tert-butoxycarbonylamino)phenyl]-L-phenylalanine methyl ester 
• 1186635-34-6 2-phenethylbenzo[f][1,7]naphthyridin-5-amine 

Relevant articles and documents

Harnessing Cascade Suzuki-Cyclization Reactions of Pyrazolo[3,4-b]pyridine for the Synthesis of Tetracyclic Fused Heteroaromatics

Numerous procedures have been described for the functionalization of pyrazolo[3,4-b]pyridine, mainly involving nucleophilic substitutions at the C-4 position or esterifications/amidations at the C-5 position. In this paper, we describe a robust, easy to implement protocol for the Suzuki cross-coupling reaction of chloroarene 2, followed by in-situ lactonization to provide chromenopyrazolopyridines. The extension of the scope of the reaction to fused naphthyridinones is also reported. This strategy gave access to 10 original pyrazolopyridine-containing tetracyclic compounds.

Small molecule thienopyrimidine-based protein tyrosine kinase inhibitors

Various thienopyrimidine-based analog compounds are able to selectively inhibit the Src family of tyrosine kinases. These compounds are useful in the treatment of various diseases including hyperproliferative diseases, hematologic diseases, osteoporosis, neurological diseases, autoimmune diseases, allergic/immunological diseases, or viral infections.

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