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107700

Sigma-Aldrich

4-(Dimethylamino)pyridine

ReagentPlus®, ≥99%

Sinônimo(s):

N,N-Dimethylpyridin-4-amine, DMAP

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About This Item

Fórmula empírica (Notação de Hill):
C7H10N2
Número CAS:
1122-58-3
Peso molecular:
122.17
Beilstein:
110354
Número CE:
214-353-5
Número MDL:
MFCD00006418
Código UNSPSC:
12352302
ID de substância PubChem:
24846774
NACRES:
NA.22

Nível de qualidade

200

linha de produto

ReagentPlus®

Ensaio

≥99%

forma

chips
crystalline powder
flakes

pf

108-110 °C (lit.)

solubilidade

H2O: 50 mg/mL

temperatura de armazenamento

room temp

cadeia de caracteres SMILES

CN(C)c1ccncc1

InChI

1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3

chave InChI

VHYFNPMBLIVWCW-UHFFFAOYSA-N

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Descrição geral

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.

Aplicação

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

Informações legais

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

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Nervous system

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

255.2 °F

Ponto de fulgor (°C)

124 °C

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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
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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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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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
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