2-bromo-N,N-diisopropylbenzamide

Base Information

• Chemical Name: 2-bromo-N,N-diisopropylbenzamide
• CAS No.: 79839-66-0
• Molecular Formula: C13H18 Br N O
• Molecular Weight: 284.196
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID30357014
• Nikkaji Number: J3.081.757E
• Wikidata: Q82136692
• Mol file: 79839-66-0.mol

Synonyms:2-bromo-N,N-diisopropylbenzamide;79839-66-0;N-Diisopropyl 2-bromobenzamide;2-bromo-N,N-di(propan-2-yl)benzamide;SCHEMBL4077020;DTXSID30357014;MFCD00583268;STL176383;AKOS003853688;BS-23753;CS-0211093;A864798

Chemical Property of 2-bromo-N,N-diisopropylbenzamide

Chemical Property:

• PSA: 20.31000
• LogP: 3.70810
• Storage Temp.: 2-8°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 283.05718
• Heavy Atom Count: 16
• Complexity: 232

Purity/Quality:

≥95% ^*data from raw suppliers

N-Diisopropyl2-bromobenzamide ^*data from reagent suppliers

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=C1Br

Technology Process of 2-bromo-N,N-diisopropylbenzamide

There total 6 articles about 2-bromo-N,N-diisopropylbenzamide 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: 99.0%

N,N-diisopropyl benzamide (20383-28-2) → o-bromo-N,N-diisopropylbenzamide (79839-66-0)

Guidance literature:

With N-Bromosuccinimide; silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid; In 1,2-dichloro-ethane; at 60 ℃; for 16h; regioselective reaction; Kinetics; Inert atmosphere;

DOI:10.1021/ja302631j

Reference yield: 90.0%

2-bromobenzoic acid chloride (7154-66-7) + diisopropylamine (108-18-9) → o-bromo-N,N-diisopropylbenzamide (79839-66-0)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1002/anie.201809929

Reference yield: 77.0%

diisopropylamine (108-18-9) + 2-bromobenzoic-acid (88-65-3) → o-bromo-N,N-diisopropylbenzamide (79839-66-0)

Guidance literature:

2-bromobenzoic-acid; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1021/jm5002277

upstream raw materials:

N,N-diisopropyl benzamide

2-bromobenzoic acid chloride

diisopropylamine

benzoyl chloride

Downstream raw materials:

N,N-diisopropyl-2-(3-methoxyanilino)benzamide

2-deuterio-N,N-diisopropylbenzamide

N,N-diisopropyl-2-(naphthalen-1-yl)benzamide

2-(benzo[d][1,3]dioxol-5-yl)-N,N-diisopropylbenzamide

Refernces

• 1、 Ghinato, Simone,Dilauro, Giuseppe,Perna, Filippo Maria,Capriati, Vito,Blangetti, Marco,Prandi, Cristina. "Directed: Ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: The organolithium base dictates the chemoselectivity". supporting information. p. 7741 - 7744. Retrieved 2019/07/12.
• 2、 Wang, Lianhui,Ackermann, Lutz. "Ruthenium-catalyzed ortho-C-H halogenations of benzamides". supporting information. p. 1083 - 1085. Retrieved 2014/01/17.