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39405 Sigma-Aldrich

4-(Dimethylamino)pyridine

purum, ≥98.0% (NT)

Synonym: N,N-Dimethylpyridin-4-amine, DMAP

  • CAS Number 1122-58-3

  • Empirical Formula (Hill Notation) C7H10N2

  • Molecular Weight 122.17

  •  Beilstein/REAXYS Number 110354

  •  EC Number 214-353-5

  •  MDL number MFCD00006418

  •  PubChem Substance ID 329755867

  •  NACRES NA.22

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Properties

Related Categories Acids & Bases, Bases, Camostat Mesylate, Chemical Synthesis, Chemicals for the synthesis of candidate COVID-19 treatments,
Quality Level   200
grade   purum
assay   ≥98.0% (NT)
form   crystals
  pellets
mp   108-110 °C (lit.)
  111-114 °C
solubility   methanol: 0.1 g/mL, clear, colorless to almost colorless
SMILES string   CN(C)c1ccncc1
InChI   1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
InChI key   VHYFNPMBLIVWCW-UHFFFAOYSA-N

Description

General description

4-(Dimethylamino)pyridine is generally employed as a catalyst in the acylation of amines, alcohols, enolates, and phenols. It can also be used in the esterification of carboxylic acids. It is known to exhibit good catalytic activity in non-polar solvents.

Application

4-(Dimethylamino)pyridine can be used:
• As a capping agent in the preparation of water-soluble gold nanoparticles.
• As an initiator in the polymerization of epoxy monomers.
• As an auxiliary reagent in the electroless preparation of gold nanotubes applicable in catalysis.
• As a catalyst in the preparation of γ- and δ-lactones via iodolactonization of γ,δ-unsaturated carboxylic acids.

A highly efficient catalyst for acylation reactions

Packaging

1 kg in glass bottle

10, 50, 250 g in glass bottle

Other Notes

Hypernucleophilic acylation catalyst. Review

Safety & Documentation

Safety Information

Signal word 
Danger
Target organs 
Nervous system
RIDADR 
UN 2811 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
US9230000
Flash Point(F) 
255.2 °F
Flash Point(C) 
124 °C

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to...
Matthias Junkers
Aldrich ChemFiles 2007, 7.2, 3.
Keywords: Acylations, Catalysis, Condensations, Dehydration reaction, Peptide synthesis, Racemizations, Solid phase peptide synthesis

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Peer-Reviewed Papers
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References

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