107700
4-(Dimethylamino)pyridine
ReagentPlus®, ≥99%
Sinónimos:
N,N-Dimethylpyridin-4-amine, DMAP
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Acerca de este artículo
Fórmula empírica (notación de Hill):
C7H10N2
Número CAS:
Peso molecular:
122.17
EC Number:
214-353-5
Beilstein/REAXYS Number:
110354
MDL number:
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
Assay:
≥99%
Concentration:
≤100%
Form:
chips, crystalline powder, flakes
Grade:
reagent grade
Servicio técnico
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reagent grade
Quality Level
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
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
signalword
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
Clase de almacenamiento
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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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 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
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