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107700

Sigma-Aldrich

4-(Dimethylamino)pyridine

ReagentPlus®, ≥99%

Sinonimo/i:

N,N-Dimethylpyridin-4-amine, DMAP

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About This Item

Formula empirica (notazione di Hill):
C7H10N2
Numero CAS:
1122-58-3
Peso molecolare:
122.17
Beilstein:
110354
Numero CE:
214-353-5
Numero MDL:
MFCD00006418
Codice UNSPSC:
12352302
ID PubChem:
24846774
NACRES:
NA.22

Grado

reagent grade

Livello qualitativo

200

Nome Commerciale

ReagentPlus®

Saggio

≥99%

Stato

chips
crystalline powder
flakes

Concentrazione

≤100%

pH

(10,23 at -0,1 g/l at 22  °C)

P. ebollizione

162 °C

Punto di fusione

108-110 °C (lit.)

Solubilità

H2O: 50 mg/mL

Gruppo funzionale

amine

Temperatura di conservazione

room temp

Stringa SMILE

CN(C)c1ccncc1

InChI

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

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Descrizione generale

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.

Applicazioni

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

Note legali

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

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Nervous system

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

255.2 °F

Punto d’infiammabilità (°C)

124 °C

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
BCBG3768V
MKBF7494V
MKBB7782
MKBD8692V
MKBD3759

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Sigma-Aldrich

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Piridina

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
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)
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
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
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