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39405

Sigma-Aldrich

4-(Dimethylamino)pyridine

purum, ≥98.0% (NT)

Synonym(s):

N,N-Dimethylpyridin-4-amine, DMAP

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About This Item

Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
1122-58-3
Molecular Weight:
122.17
Beilstein/REAXYS Number:
110354
EC Number:
214-353-5
MDL number:
MFCD00006418
UNSPSC Code:
12352005
PubChem Substance ID:
329755867
NACRES:
NA.22

Key Documents

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grade

purum

Quality Level

200

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

functional group

amine

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

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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

Other Notes

Hypernucleophilic acylation catalyst.

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Danger

Hazard Classifications

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

target_organs

Nervous system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

255.2 °F

flash_point_c

124 °C

ppe

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

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Certificates of Analysis (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)
Giovanna Cutrone et al.
Carbohydrate polymers, 223, 115085-115085 (2019-08-21)
Nanoparticles made of metal-organic frameworks (nanoMOFs) are becoming of increasing interest as drug carriers. However, engineered coatings such as poly(ethylene glycol) (PEG) based ones are required to prevent nanoMOFs recognition and clearance by the innate immune system, a prerequisite for
Yi Zhang et al.
ACS applied materials & interfaces, 11(50), 46427-46436 (2019-11-26)
A kind of specific cyclodextrin polyrotaxanes (PRs) drug delivery system was developed for an effective drug delivery and enhancing antitumor effect. In this work, we prepared the PR by using α-CD derivatives and dicarboxyl-PEG (Mn = 4200) self-assembling and end-capping
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