79606-46-5

Basic information

• Product Name: 4-Bromo-N,N-diisopropylbenzamide
• Synonyms: 4-Bromo-N,N-diisopropylbenzamide;N-Diisopropyl 4-bromobenzamide;BenzaMide, 4-broMo-N,N-bis(1-Methylethyl)-
• CAS NO: 79606-46-5
• Molecular Formula: C₁₃H₁₈BrNO
• Molecular Weight: 284.19
• Product Categories: blocks;Bromides;Carboxes
• Mol File: 79606-46-5.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 362.8°C at 760 mmHg
• Flash Point: 173.2°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Bromo-N,N-diisopropylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-N,N-diisopropylbenzamide(79606-46-5)
• EPA Substance Registry System: 4-Bromo-N,N-diisopropylbenzamide(79606-46-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 79606-46-5(Hazardous Substances Data)

Usage

General Description

4-Bromo-N,N-diisopropylbenzamide, also known as bromadoline, is a chemical compound with the molecular formula C15H20BrNO. It is a white to off-white solid with a molecular weight of 298.23 g/mol. This chemical is commonly used in research and development as a building block for the synthesis of other organic compounds. It is also known for its potential use as a bioactive compound, with studies showing its possible activity as a potential analgesic and anti-inflammatory agent. Additionally, it has shown potential for use in the development of new drugs, particularly in the field of pharmaceuticals. Overall, 4-Bromo-N,N-diisopropylbenzamide is a versatile chemical with potential applications in various fields, making it a valuable compound for research and development purposes.

InChI:InChI=1/C13H18BrNO/c1-9(2)15(10(3)4)13(16)11-5-7-12(14)8-6-11/h5-10H,1-4H3

Upstream product

• 201230-82-2 carbon monoxide 
• 5467-74-3 4-Bromophenylboronic acid 
• 108-18-9 diisopropylamine 
• 586-76-5 4-Bromobenzoic acid 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 586-75-4 4-chlorobenzoyl chloride 
• 5419-55-6 Triisopropyl borate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 4111-54-0 lithium diisopropyl amide 

Downstream Products

• 1058129-82-0 {5-bromo-2-[(diisopropylamino)carbonyl]phenyl}boronic acid 
• 1429609-72-2 C₁₆H₂₂N₂O₂ 
• 1609554-27-9 N,N-diisopropyl 4-[1-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]benzamide 
• 327057-57-8 N,N-diisopropyl-4-(2-methoxy-quinolin-6-yl)-benzamide 
• 586-76-5 4-Bromobenzoic acid 
• 336182-29-7 4-bromo-N-isopropyl-benzamide 
• 850568-33-1 (4-(diisopropylcarbamoyl)phenyl)boronic acid 
• 67289-11-6 4-cyano-N,N-diisopropylbenzamide 

Relevant articles and documents

Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates

Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.

Amide Effects in C?H Activation: Noncovalent Interactions with L-Shaped Ligand for meta Borylation of Aromatic Amides

A new concept for the meta-selective borylation of aromatic amides is described. It has been demonstrated that while esters gave para borylations, amides lead to meta borylations. For achieving high meta selectivity, an L-shaped bifunctional ligand has been employed and engages in an O???K noncovalent interaction with the oxygen atom of the moderately distorted amide carbonyl group. This interaction provides exceptional control for meta C?H activation/borylation.

Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration

Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.