Structure via PubChem · Public domain (PubChem)
4-dimethylaminopyridine
Sign in to saveAlso known as DMAP
4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent.
Chemical data
- Formula
- C7H10N2
- Molecular weight
- 122.17 g/mol
- IUPAC name
- N,N-dimethylpyridin-4-amine
- SMILES
- CN(C)C1=CC=NC=C1
- InChIKey
- VHYFNPMBLIVWCW-UHFFFAOYSA-N
- XLogP
- 1.3
- Polar surface area
- 16.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Has part
- hydrogen
- Mass
- 122.084
Show 6 more facts
- chemical formula
- C₇H₁₀N₂
- canonical SMILES
- CN(C)C1=CC=NC=C1
- Commons category
- DMAP
- boiling point
- 162
- melting point
- 112.0
- found in taxon
- Panax ginseng
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Preparation
- Esterification catalyst
- Safety
- Related compound
- References
- Further reading
4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe2 substituent.
Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxiliary type amides.
Excerpted from Wikipedia’s “4-dimethylaminopyridine” article, available under the CC BY-SA 4.0 licence.