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Merck

107700

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
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

Key Documents

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InChI key

VHYFNPMBLIVWCW-UHFFFAOYSA-N

InChI

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

SMILES string

CN(C)c1ccncc1

grade

reagent grade

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

Quality Level

200

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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

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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

107700-CH: + 107700-25KG: + 107700-5G: + 107700-25G: + 107700-1KG: + 107700-BULK: + 107700-VAR: + 107700-500G: + 107700-5KG: + 107700-10KG: + 107700-100G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBG3768V
MKBF7494V
MKBB7782
MKBD8692V
MKBD3759

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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
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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