903895-48-7

Basic information

• Product Name: 3-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER
• Synonyms: TERT-BUTYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE;3-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER;3-(t-butoxycarbonyl)henyl boronicacid pinacol ester
• CAS NO: 903895-48-7
• Molecular Formula: C17H25BO4
• Molecular Weight: 304.19
• Product Categories: Heterocyclic Compounds;Aryl;Boronic ester;Organoborons
• Mol File: 903895-48-7.mol

Chemical Properties

• Boiling Point: 396.7°C at 760 mmHg
• Flash Point: 193.7°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 1.68E-06mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER(903895-48-7)
• EPA Substance Registry System: 3-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER(903895-48-7)

Safety Data

• Hazardous Substances Data: 903895-48-7(Hazardous Substances Data)

Usage

Uses

3-t-Butoxycarbonylphenylboronic acid, pinacol ester

InChI:InChI=1/C17H25BO4/c1-15(2,3)20-14(19)12-9-8-10-13(11-12)18-21-16(4,5)17(6,7)22-18/h8-11H,1-7H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 220210-56-0 3-(tert-butoxycarbonyl)phenylboronic acid 
• 69038-74-0 tert-butyl 3-bromobenzoate 
• 73183-34-3 bis(pinacol)diborane 
• 585-76-2 m-bromobenzoic acid 
• 831-34-5 tert-butyl 3-fluorobenzoate 

Relevant articles and documents

EIF4E-INHIBITING 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE COMPOUNDS

The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X1, X2, X3, X4, X5, X6, Q, L1, L2, Y, R1, R2, R3, R4, R5, R6, R7, R8 and rings A, B and C are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4e and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles

We herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated rhodium complex with two dimethyl groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.

Copper-Catalyzed ipso-Borylation of Fluoroarenes

ipso-Borylation of fluoroarenes has been achieved using an air-stable copper complex as a catalyst. Mechanistic studies suggest that the reaction proceeds via an SRN1 mechanism involving a single-electron-transfer (SET) process and not via the typical SNAr mechanism. This method differs from the previously reported nickel/copper-cocatalyzed system in terms of scope of the substrate and has exhibited good scalability. Double and triple ipso-borylations of several di- and trifluoroarenes have been also achieved efficiently, enhancing the synthetic utility of this method.