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107700

4-(Dimethylamino)pyridine

Name: 4-(Dimethylamino)pyridine
Brand: ALDRICH

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

UNSPSC Code:

12352302

NACRES:

NA.22

PubChem Substance ID:

24846774

EC Number:

214-353-5

Beilstein/REAXYS Number:

110354

MDL number:

MFCD00006418

Assay:

≥99%

Concentration:

≤100%

Form:

chips, crystalline powder, flakes

Grade:

reagent grade

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Properties

grade

reagent grade

Quality Level

200

product line

ReagentPlus^®

assay

≥99%

form

chips, crystalline powder, flakes

concentration

≤100%

pH

(10,23 at -0,1 g/l at 22 °C)

bp

162 °C

mp

108-110 °C (lit.)

solubility

H₂O: 50 mg/mL

functional group

amine

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

Description

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

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pictograms

GHS06,GHS08,GHS05,GHS09

signalword

Danger

hcodes

H301 + H331,H310,H315,H318,H370,H411

pcodes

P262 - P273 - P280 - P301 + P310 - P302 + P352 + P310 - P305 + P351 + P338

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

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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Powerful Ti-crossed Claisen condensation between ketene silyl acetals or thioacetals and acid chlorides or acids.

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

A new approach for generic screening and quantitation of potential genotoxic alkylation compounds by pre-column derivatization and LC-MS/MS analysis.

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

Capture and visualization of hydrogen sulfide by a fluorescent probe.

Chunrong Liu et al.

Angewandte Chemie (International ed. in English), 50(44), 10327-10329 (2011-09-08)

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Global Trade Item Number

SKU	GTIN
CDS001275-1G	04061825962719
107700-5KG	04061833458617
107700-25G	04061835554065
107700-500G	04061838675477
107700-5G	04061835554072
107700-100G	04061835554058