79606-43-2

Basic information

• Product Name: N,N-DIISOPROPYL-4-METHOXYBENZAMIDE
• Synonyms: N,N-DIISOPROPYL-4-METHOXYBENZAMIDE;4-Methoxy-N,N-bis(1-methylethyl)benzamide;N,N-Diisopropyl-p-anisamide
• CAS NO: 79606-43-2
• Molecular Formula: C₁₄H₂₁NO₂
• Molecular Weight: 235.32
• Mol File: 79606-43-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 359.4 °C at 760 mmHg
• Flash Point: 171.1 °C
• Appearance: /
• Density: 0.999 g/cm³
• Vapor Pressure: 2.39E-05mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: N,N-DIISOPROPYL-4-METHOXYBENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-DIISOPROPYL-4-METHOXYBENZAMIDE(79606-43-2)
• EPA Substance Registry System: N,N-DIISOPROPYL-4-METHOXYBENZAMIDE(79606-43-2)

Safety Data

• Hazardous Substances Data: 79606-43-2(Hazardous Substances Data)

Usage

General Description

N,N-Diisopropyl-4-methoxybenzamide is a chemical compound that belongs to the class of benzamides. It is a white solid that is used as a pharmaceutical intermediate and as a building block in organic synthesis. N,N-DIISOPROPYL-4-METHOXYBENZAMIDE is commonly used in the production of various pharmaceuticals and is also utilized as an intermediate in the synthesis of other organic compounds. It has the molecular formula C13H21NO2 and a molecular weight of 223.31 g/mol. N,N-Diisopropyl-4-methoxybenzamide is known to have mild to moderate acute toxicity and should be handled and used with appropriate safety precautions.

InChI:InChI=1/C14H21NO2/c1-10(2)15(11(3)4)14(16)12-6-8-13(17-5)9-7-12/h6-11H,1-5H3

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 108-18-9 diisopropylamine 
• 937-29-1 4-methoxybenzoyl bromide 
• 5419-55-6 Triisopropyl borate 
• 874-90-8 4-methoxybenzonitrile 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 4111-54-0 lithium diisopropyl amide 
• 121-98-2 methyl 4-methoxybenzoate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 696-62-8 para-iodoanisole 
• 116858-79-8 tributyl-N,N-di-isopropylcarbamoylstannane 
• 116858-82-3 (N,N-diisopropylcarbamoyl)(trimethyl)stannane 
• 98-01-1 furfural 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 

Downstream Products

• 253308-75-7 2-hydroxymethyl-4-methoxy-N,N-diisopropylbenzamide 
• 123-11-5 4-methoxy-benzaldehyde 
• 335371-38-5 2-diisopropylcarbamoyl-5-methoxyphenylboronic acid 
• 1023-17-2 4-methoxyphenyl benzyl ketone 
• 1001351-06-9 2-iodo-N,N-diisopropyl-4-methoxybenzamide 
• 1671-76-7 p-Methoxyvalerophenon 
• 135277-40-6 5-(4-methoxyphenyl)nonan-5-ol 
• 1250259-31-4 N-(4-methoxybenzyl)-N-isopropylpropan-2-amine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 88932-60-9 4-Methoxy-2-(trimethylsilyl)benzaldehyde 

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.

Identification of key functionalization species in the Cp?Ir(iii)-catalyzed-: ortho halogenation of benzamides

Cp?Ir(iii) complexes have been shown to be effective for the halogenation of N,N-diisopropylbenzamides with N-halosuccinimide as a suitable halogen source. The optimized conditions for the iodination reaction consist of 0.5 mol% [Cp?IrCl2]2 in 1,2-dichlor

Chemoselective Reduction of Sterically Demanding N,N-Diisopropylamides to Aldehydes

A sequential one-pot process for chemoselectively reducing sterically demanding N,N-diisopropylamides to aldehydes has been developed. In this reaction, amides are activated with EtOTf to form imidates, which are reduced with LiAlH(OR)3 [R = t-Bu, Et] to give aldehydes by hydrolysis of the resulting hemiaminals. The non-nucleophilic base 2,6-DTBMP remarkably improves reaction efficiency. The combination of EtOTf/2,6-DTBMP and LiAlH(O-t-Bu)3 was found to be optimal for reducing alkyl, alkenyl, alkynyl, and 2-monosubstituted aryl N,N-diisopropylamides. In contrast, EtOTf and LiAlH(OEt)3 in the absence of base were found to be optimal for reducing extremely sterically demanding 2,6-disubstituted N,N-diisopropylbenzamides. The reaction tolerates various reducible functional groups, including aldehyde and ketone. 1H NMR studies confirmed the formation of imidates stable in water. The synthetic usefulness of this methodology was demonstrated with N,N-diisopropylamide-directed ortho-metalation and C-H bond activation.