N,N-Diisopropyl-2-phenylbenzamide

Base Information

• Chemical Name: N,N-Diisopropyl-2-phenylbenzamide
• CAS No.: 103681-91-0
• Molecular Formula: C19H23NO
• Molecular Weight: 281.398
• DSSTox Substance ID: DTXSID50359616
• Nikkaji Number: J622.166A
• Wikidata: Q82140904
• ChEMBL ID: CHEMBL1408831
• Mol file: 103681-91-0.mol

Synonyms:STK225823;103681-91-0;HMS2334H09;SMR000142933;MLS000535497;CHEMBL1408831;DTXSID50359616;N,N-diisopropyl-2-phenyl-benzamide;N,N-diisopropyl-2-biphenylcarboxamide;AKOS003340287;N,N-di(propan-2-yl)biphenyl-2-carboxamide;N,N-diisopropyl[1,1'-biphenyl]-2-carboxamide

Chemical Property of N,N-Diisopropyl-2-phenylbenzamide

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 281.177964357
• Heavy Atom Count: 21
• Complexity: 323

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(C(C)C)C(=O)C1=CC=CC=C1C2=CC=CC=C2

Technology Process of N,N-Diisopropyl-2-phenylbenzamide

There total 1 articles about N,N-Diisopropyl-2-phenylbenzamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phenylmagnesium bromide + 2-(tert-butylsulfonyl)-N,N-diisopropylbenzamide (155496-72-3) → N,N-diisopropyl benzamide (20383-28-2) + N,N-diisopropyl-[1,1'-biphenyl]-2-carboxamide (103681-91-0)

Guidance literature:

With bis(acetylacetonate)nickel(II); In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1039/c39930001682

Reference yield: 73.0%

N,N-diisopropyl-[1,1'-biphenyl]-2-carboxamide (103681-91-0) + bis(pinacol)diborane (73183-34-3) → C25H34BNO3

Guidance literature:

bis(pinacol)diborane; With 5-methyl-2-(thiophen-3-yl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 20 ℃; for 0.0333333h; Inert atmosphere; Glovebox;

N,N-diisopropyl-[1,1'-biphenyl]-2-carboxamide; In tetrahydrofuran; at 100 ℃; for 24h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.0c13415

Reference yield:

N,N-diisopropyl-[1,1'-biphenyl]-2-carboxamide (103681-91-0) → 2-Phenylbenzaldehyde (1203-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane; tetrahydrofuran / -78 - 20 °C / Inert atmosphere

2: lithium tri-t-butoxyaluminum hydride / dichloromethane; tetrahydrofuran / 4 h / -78 °C / Inert atmosphere

With 2,6-di-tert-butyl-4-methylpyridine; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.joc.7b02868

upstream raw materials:

2-(tert-butylsulfonyl)-N,N-diisopropylbenzamide

Downstream raw materials:

3-Naphthalen-1-yl-biphenyl-2-carboxylic acid diisopropylamide

2-Phenylbenzaldehyde

Refernces

• 1、 Clayden, Jonathan,Julia, Marc. "ortho-Substituted Unsymmetrical Biaryls from Aryl tert-Butyl Sulfones". . p. 1682 - 1683. Retrieved 2007/10/02.