82860-53-5

Basic information

• Product Name: 2-hydroxy-N,N-di(propan-2-yl)benzamide
• CAS NO: 82860-53-5
• Molecular Formula: C₁₃H₁₉NO₂
• Molecular Weight: 221.2955
• Mol File: 82860-53-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 354.2°C at 760 mmHg
• Flash Point: 168°C
• Density: 1.054g/cm³
• Vapor Pressure: 1.67E-05mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 2-hydroxy-N,N-di(propan-2-yl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-N,N-di(propan-2-yl)benzamide(82860-53-5)
• EPA Substance Registry System: 2-hydroxy-N,N-di(propan-2-yl)benzamide(82860-53-5)

Safety Data

• Hazardous Substances Data: 82860-53-5(Hazardous Substances Data)

Upstream product

• 20383-28-2 N,N-diisopropyl benzamide 
• 444-30-4 2-(trifluoromethyl)phenol 
• 108-18-9 diisopropylamine 
• 1228447-84-4 2-(isopropoxydimethylsilyl)-N,N-diisopropylbenzamide 
• 1441-87-8 salicyloyl chloride 
• 69-72-7 salicylic acid 
• 98-88-4 benzoyl chloride 
• 142075-48-7 phenyl N,N-diisopropylcarbamate 

Downstream Products

• 63026-69-7 ortho-diisopropylaminomethylphenol 

Relevant articles and documents

Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination

Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.

Aryl Carbamates: Mechanisms of Orthosodiations and Snieckus-Fries Rearrangements

Aryl carbamates are orthometalated by sodium diisopropylamide (NaDA) in tetrahydrofuran. The resulting arylsodiums undergo Snieckus-Fries rearrangement to give orthoacylated phenols in good yield. The intermediate arylsodiums and resulting orthoacylated phenolates are suggested to be monomeric. The rate-limiting step in the two-step sequence depends on the steric demands of the carbamoyl moiety and the substituents in the meta position of the arene. Rate studies reveal a dominant disolvated-monomer-based orthometalation followed by a di- or trisolvated arylsodium monomer-based rearrangement. Kinetic evidence of a NaDA-catalyzed Snieckus-Fries rearrangement suggests the intermediacy of mixed trimers. Competitive halide eliminations to form benzyne are also discussed.

Diastereoselective synthesis of trans-3,5-disubstituted dihydrofuran-2(3H)-ones via SmI2-mediated reductive coupling of 2-alkylacrylates of N,N-diisopropyl-2-hydroxybenzamide with aldehydes

Samarium(II) diiodide has been used to mediate reductive coupling reactions of aldehydes with a variety of substituted acrylates, in both achiral and chiral forms, for accessing substituted dihydrofuran-2(3H)-ones (γ-butyrolactones). Two major issues, concerning with self-dimerization of α-non-branched aliphatic aldehydes and low diastereoselectivity of the products, render limited application of the reductive coupling protocol in total synthesis of natural products. We report here on a novel type of substituted acrylates derived from the 2-amido arenols (HO-Aram) such as N,N-diisopropyl-2-hydroxybenzamide. The acrylates of HO-Aram enable: (a) preferential conjugate reduction of the acrylates than carbonyl reduction of aliphatic aldehydes, leading to diminished aldehyde self-dimerization; and (b) organization of an eight-membered ring among the amide carbonyl oxygen atom and samarium(III) to form a 7/8-bicyclic transition state, resulting in highly diastereoselective protonation of the samarium(III) enolate intermediate. Examples of synthesis of trans-3,5-disubstituted dihydrofuran-2(3H)-ones from 2-alkylacrylates of HO-Aram and aliphatic aldehydes are provided.