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39405

Sigma-Aldrich

4-(Dimethylamino)pyridine

purum, ≥98.0% (NT)

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Synonym(s):
N,N-Dimethylpyridin-4-amine, DMAP
Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
Molecular Weight:
122.17
Beilstein:
110354
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

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

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1 of 4

This Item
107700PHR29258.20499
assay

≥98.0% (NT)

assay

≥99%

assay

-

assay

≥99.0% (GC)

form

crystals, pellets

form

chips, crystalline powder, flakes

form

solid

form

solid

mp

108-110 °C (lit.), 111-114 °C

mp

108-110 °C (lit.)

mp

108-110 °C (lit.)

mp

110-112 °C

solubility

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

solubility

H2O: 50 mg/mL

solubility

-

solubility

60 g/L

Quality Level

200

Quality Level

200

Quality Level

300

Quality Level

200

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. Review

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

255.2 °F

Flash Point(C)

124 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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4-(Dimethylamino) pyridine-catalysed iodolactonisation of γ, δ-unsaturated carboxylic acids
Meng C, et al.
Organic & Biomolecular Chemistry, 13(24), 6766-6772 (2015)
Homopolymerization of epoxy monomers initiated by 4-(dimethylamino) pyridine
Dell'Erba IE and Williams RJ
Polym. Eng. Sci., 46(3), 351-359 (2006)
4-Dimethylamino-pyridine (DMAP)
Grondal C
Synlett, 2003(10), 1568-1569 (2003)
E.F. Scriben
Chemical Society Reviews, 13, 129-129 (1983)
Assessment of 4-(dimethylamino) pyridine as a capping agent for gold nanoparticles
Gandubert VJ and Lennox RB
Langmuir, 21(14), 6532-6539 (2005)

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