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39405

Sigma-Aldrich

4-(Dimethylamino)pyridine

purum, ≥98.0% (NT)

Sinonimo/i:

N,N-Dimethylpyridin-4-amine, DMAP

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About This Item

Formula empirica (notazione di Hill):
C7H10N2
Numero CAS:
1122-58-3
Peso molecolare:
122.17
Beilstein:
110354
Numero CE:
214-353-5
Numero MDL:
MFCD00006418
Codice UNSPSC:
12352005
ID PubChem:
329755867
NACRES:
NA.22

Grado

purum

Livello qualitativo

200

Saggio

≥98.0% (NT)

Forma fisica

crystals
pellets

Punto di fusione

108-110 °C (lit.)
111-114 °C

Solubilità

methanol: 0.1 g/mL, clear, colorless to almost colorless

Gruppo funzionale

amine

Stringa SMILE

CN(C)c1ccncc1

InChI

1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
VHYFNPMBLIVWCW-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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

Altre note

Hypernucleophilic acylation catalyst. Review

Avvertenze

Danger

Classi di pericolo

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 1

Organi bersaglio

Nervous system

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

255.2 °F

Punto d’infiammabilità (°C)

124 °C

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
WXBD5727V
WXBD4805V
WXBD2693V
WXBD2319V
WXBD1308V

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A. Hassner
Tetrahedron, 34, 2069-2069 (1978)
E.F. Scriben
Chemical Society Reviews, 13, 129-129 (1983)
Hoefle, G., et al.
Angewandte Chemie (International Edition in English), 90, 602-602 (1978)
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Articoli

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 the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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