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Sigma-Aldrich

4-(Dimethylamino)pyridine

ReagentPlus®, ≥99%

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:
110354
EC Number:
214-353-5
MDL number:
MFCD00006418
UNSPSC Code:
12352302
PubChem Substance ID:
24846774
NACRES:
NA.22

Quality Level

200

product line

ReagentPlus®

Assay

≥99%

form

chips
crystalline powder
flakes

mp

108-110 °C (lit.)

solubility

H2O: 50 mg/mL

storage temp.

room temp

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 (DMAP) is a highly versatile nucleophilic catalyst for acylation reactions and esterifications. It is also employed in various organic transformations like Baylis-Hillman reaction, Dakin-West reaction, protection of amines, C-acylations, silylations, applications in natural products chemistry, and many others.

Application

4-(Dimethylamino)pyridine can be used as a catalyst:
  • To synthesize 3,5-disubstituted 2,6-dicyanoaniline by reacting malononitrile, aldehydes, and β-nitroolefins.
  • For the acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to synthesize corresponding esters.
  • In Baylis-Hillman reaction to form carbon-carbon bond by the coupling of an activated alkene with an aldehyde or ketone.
A highly efficient catalyst for acylation reactions

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Akira Iida et al.
Organic letters, 8(23), 5215-5218 (2006-11-03)
[Structure: see text] A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give alpha-monoalkylated esters and thermodynamically unfavorable (less accessible) alpha,alpha-dialkylated beta-keto esters in good yield (46 examples; 41-98% yield). A closely
Chenghu Yan et al.
Biomacromolecules, 10(8), 2013-2018 (2009-09-03)
An effective method for grafting L-lactide (LA) from unmodified cellulose by ring-opening polymerization (ROP) in homogeneous mild conditions is presented. By using 4-dimethylaminopyridine (DMAP) as an organic catalyst, cellulose-graft-poly(L-lactide) (cellulose-g-PLLA) copolymers with a molar substitution (MS(PLLA)) of PLLA in a
Hangxiang Wang et al.
Journal of the American Chemical Society, 133(31), 12220-12228 (2011-07-19)
Catalysts hold promise as tools for chemical protein modification. However, the application of catalysts or catalyst-mediated reactions to proteins has only recently begun to be addressed, mainly in in vitro systems. By radically improving the affinity-guided DMAP (4-dimethylaminopyridine) (AGD) catalysts
A M van Wijk et al.
Analytical and bioanalytical chemistry, 400(5), 1375-1385 (2011-03-30)
A generic LC-MS/MS method was developed for the analysis of potentially genotoxic alkyl halides. A broad selection of alkyl halides were derivatized using 4-dimethylaminopyridine in acetonitrile. The reaction conditions for derivatization, i.e., solvent, reaction time, temperature and concentration of alkyl
Min Suk Shim et al.
Journal of controlled release : official journal of the Controlled Release Society, 133(3), 206-213 (2008-11-11)
To maximize therapeutic effects, targeted delivery of nucleic acids (e.g., DNA and RNA) in their appropriate intracellular targets is highly desirable. In this study, primary amines of a model polymeric nonviral carrier, polyethylenimine (PEI), at two molecular weights (0.8 and
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