All Photos(5)

107700

Sigma-Aldrich

4-(Dimethylamino)pyridine

ReagentPlus®, ≥99%

Synonym(s):
N,N-Dimethylpyridin-4-amine, DMAP
Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
Molecular Weight:
122.17
Beilstein:
110354
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

≥99%

form

chips
crystalline powder
flakes

mp

108-110 °C (lit.)

solubility

H2O: 50 mg/mL

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

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Packaging

5 kg in fiber drum
5, 25, 100, 500 g in glass bottle

Application

Used in conjunction with TiCl4 in a Claisen condensation between ketene silyl acetals and carboxylic acids leading to ß-keto esters.
A highly efficient catalyst for acylation reactions

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

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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 Code

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

WGK Germany

WGK 3

Flash Point F

255.2 °F

Flash Point C

124 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

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)
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...
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...

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