2376879-92-2

Basic information

• Product Name: 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one
• CAS NO: 2376879-92-2
• Molecular Weight: 327.231
• Mol File: 2376879-92-2.mol

Chemical Properties

• CAS DataBase Reference: 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one(2376879-92-2)
• EPA Substance Registry System: 2,2-dimethyl-1-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-1-yl)propan-1-one(2376879-92-2)

Safety Data

• Hazardous Substances Data: 2376879-92-2(Hazardous Substances Data)

Usage

Chemical class

ketones

Derivative

indole

Functional group

boronic ester

Usage

reagent for the introduction of the boron atom

Application

building block for the synthesis of pharmaceuticals and biologically active compounds

Unique property

chemical reactivity due to the presence of the boron atom

Value

valuable tool in chemical and pharmaceutical research

Upstream product

• 3282-30-2 pivaloyl chloride 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 70957-04-9 N-pivaloyl indole 
• 10294-33-4 boron tribromide 
• 120-72-9 indole 

Downstream Products

• 642494-37-9 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole 

Relevant articles and documents

Preparation method of indole type or aniline type borate

The invention discloses a preparation method of indole type or aniline type borate, which comprises the following step: reacting an indole type raw material or aniline type raw material with boron trihalide in an organic solvent under the protection of in

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.