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  1. Wikipedia
    https://en.wikipedia.org/wiki/4-Dimethylaminopyridine

    4-Dimethylaminopyridine - Wikipedia

    • In the case of esterification with acetic anhydrides the currently accepted mechanism involves three steps. First, DMAP and acetic anhydride react in a pre-equilibrium reaction to form an ion pair of acetate and the acetylpyridinium ion. In the second step the alcohol adds to the acetylpyridinium, and elimination of pyridine forms an ester. Here the acetate acts … See more

    Overview

    4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This white solid is of interest because it is m…

    Preparation

    DMAP can be prepared in a two-step procedure from pyridine, which is first oxidized to 4-pyridylpyridinium cation. This cation then reacts with dimethylamine:

    Safety

    DMAP has a relatively high toxicity and is particularly dangerous because of its ability to be absorbed through the skin. It is also corrosive.

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  1. Showing results for DMAP Reagent Mechanism
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  2. Studies of DMAP Rea. Get Mechanism
    National Center for Biotechnology Information
    Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions
    Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions wit...
    Author: Hiroki Mandai, …
    Published: 2016
    Publication: Nat Com…
    PubMed
    4-(N,N-Dimethylamino)pyridine hydrochloride as a recyclable catalyst for acylation of inert alcohols: substrate scope and reaction mechanism
    4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP·HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions. The reaction mechanism was investigated in detail for the first time; DMAP·HCl and the acylat...
    Author: Zhihui Liu
    Published: 2014/01/03
    Keywords: National In…
    Chemistry Europe
    The DMAP-Catalyzed Acetylation of Alcohols—A Mechanistic Study (DMAP=4-(Dimethylamino)pyridine)
    The acetylation of tert-butanol with acetic anhydride catalyzed by 4-(dimethylamino)pyridine (DMAP) has been studied at the Becke3 LYP/6-311+G(d,p)//Becke3 LYP/6-31G(d) level of theory. Solvent effects have been estimated through single-point calculations with the PCM/UAHF solvation model. The energ...
    Author: Shangjie Xu D…
    Published: 25 July 2005
    Cited By: 257
  3. Organic Chemistry Portal
    https://www.organic-chemistry.org/namedreactions/...

    Yamaguchi Esterification - Organic Chemistry Portal

  4. ACS Publications
    https://pubs.acs.org/doi/10.1021/ol4030875

    4-(N,N-Dimethylamino)pyridine Hydrochloride as a …

    Dec 16, 2013 · 4-(N,N-Dimethylamino)pyridine hydrochloride (DMAP·HCl), a DMAP salt with the simplest structure, was used as a recyclable catalyst for the acylation of inert alcohols and phenols under base-free conditions.

  5. National Center for Biotechnology Information
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4835565

    Enantioselective acyl transfer catalysis by a combination of …

  6. Organic Chemistry Portal
    https://www.organic-chemistry.org/name…

    Steglich Esterification - Organic Chemistry Portal

    A common explanation of the DMAP acceleration suggests that DMAP, as a stronger nucleophile than the alcohol, reacts with the O -acylisourea leading to a reactive amide ("active ester"). This intermediate cannot form intramolecular …

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  8. Common Organic Chemistry
    https://commonorganicchemistry.com/Common_Reagents/...

    4-Dimethylaminopyridine (DMAP) - Common Organic Chemistry

  9. ACS Publications
    https://pubs.acs.org/doi/10.1021/acsomega.…

    Unveiling the Role of DMAP for the Se-Catalyzed …

    Mar 11, 2024 · Based on these findings, we suggested a plausible reaction mechanism. Notably, DMAP exhibited dual-functional behavior, acting as both a nucleophile and HB acceptor, which is responsible for the remarkable …

  10. Online Organic Chemistry Tutor
    https://onlineorganicchemistrytutor.com/…

    Yamaguchi Esterification - Online Organic Chemistry …

    Apr 20, 2024 · The Yamaguchi esterification is the coupling organic chemistry reaction where the ester is formed from a carboxylic acid in presence of alcohol, triethylamine, 2,4-trichlorobenzoyl chloride i.e. Yamaguchi reagent and DMAP …

  11. PubMed
    https://pubmed.ncbi.nlm.nih.gov/24328854

    4-(N,N-Dimethylamino)pyridine hydrochloride as a recyclable

  12. Common Organic Chemistry
    http://commonorganicchemistry.com/Rx…

    Boc Protection Mechanism (Boc2O + DMAP)

    DMAP should accelate the rate of the boc protection reaction but also makes side reactions more likely. A detailed mechanism illustrating boc protection using boc anhydride (Boc2O) and 4-Dimethylaminopyridine (DMAP).

  14. Showing results for DMAP Reagent Mechanism
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