107700

4-(Dimethylamino)pyridine

ReagentPlus^®, ≥99%

• Synonym(s): N,N-Dimethylpyridin-4-amine, DMAP
• Empirical Formula (Hill Notation): C₇H₁₀N₂
• CAS Number: 1122-58-3
• Molecular Weight: 122.17
• Beilstein: 110354
• EC Number: 214-353-5
• MDL number: MFCD00006418
• PubChem Substance ID: 24846774
• NACRES: NA.22

Properties

• Quality Level: 200
• 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

Description

General description

4-(Dimethylamino)pyridine 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

Packaging

5, 25, 100, 500 g in glass bottle

1, 5, 10, 25 kg

Legal Information

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

Safety Information

• Pictograms: GHS05,GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H331 - H310 - H315 - H318 - H370 - H411
• Precautionary Statements: P262 - P273 - P280 - P301 + P310 - P302 + P352 + P310 - P305 + P351 + P338
• 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: WGK 3
• Flash Point(F): 255.2 °F
• Flash Point(C): 124 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves