4-Dimethylaminopyridine
[CAS# 1122-58-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Aminopyridine
• Name: 4-Dimethylaminopyridine
• Synonyms: N,N-Dimethylpyridin-4-amine; DMAP
• Molecular Formula: C₇H₁₀N₂
• Molecular Weight: 122.17
• CAS Registry Number: 1122-58-3
• EC Number: 214-353-5
• SMILES: CN(C)C1=CC=NC=C1

Properties

• Melting point: 108-113 °C
• Boiling point: 162 °C (50 mmHg)
• Flash point: 110 °C
• Water solubility: 76 g/L (25 °C)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08;GHS09 Danger
• Risk Statements: H301-H310-H314-H315-H318-H319-H331-H335-H370-H411
• Safety Statements: P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P308+P316-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	2	H310
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	3	H331
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	1	H310
Skin corrosion	Skin Corr.	1B	H314
Specific target organ toxicity - single exposure	STOT SE	1	H370
Skin corrosion	Skin Corr.	1C	H314
Acute toxicity	Acute Tox.	3	H311
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Germ cell mutagenicity	Muta.	2	H341
Skin corrosion	Skin Corr.	1	H314
Specific target organ toxicity - single exposure	STOT SE	3	H336

• Transport Information: UN 1760; UN 2811

Discovery and Applications

4-Dimethylaminopyridine (DMAP), with the chemical formula C₈H₁₀N₂, is a heterocyclic organic compound known for its strong basicity and nucleophilicity. It features a pyridine ring substituted with a dimethylamino group at the 4-position. This compound is a valuable reagent in organic synthesis and catalysis due to its unique chemical properties.

The discovery of DMAP is rooted in the study of pyridine derivatives, which began in the 19th century. Pyridine itself was first synthesized in 1849 by the German chemist August Friedlieb Runge. The introduction of the dimethylamino group to the pyridine ring, leading to the formation of 4-dimethylaminopyridine, was explored in the mid-20th century as researchers sought to enhance the reactivity of pyridine-based compounds.

DMAP is widely recognized for its role as a catalytic agent in various chemical reactions. One of its most notable applications is in esterification and acylation reactions. DMAP acts as a nucleophilic catalyst that facilitates the formation of esters and amides from carboxylic acids and alcohols or amines. This catalytic activity is attributed to the strong basicity of the dimethylamino group, which enhances the electrophilicity of the carbonyl group, making it more reactive towards nucleophiles.

In addition to its role in esterification, DMAP is employed in the synthesis of pharmaceuticals and fine chemicals. It is used in the production of various drugs, where it helps in the formation of complex molecules through acylation and esterification processes. DMAP’s ability to accelerate these reactions makes it a valuable tool in the pharmaceutical industry for developing new compounds and optimizing synthetic routes.

DMAP is also utilized in the field of polymer chemistry. It serves as a catalyst in the polymerization of certain monomers, contributing to the synthesis of polymers with specific properties. The compound's catalytic activity is harnessed to produce high-performance materials used in various industrial applications.

Despite its utility, DMAP must be handled with care due to its toxicity and potential health hazards. Safety protocols are essential when working with this compound to avoid exposure and ensure safe handling practices.

Overall, 4-dimethylaminopyridine's discovery and development have established it as a crucial reagent in organic synthesis and catalysis. Its applications in esterification, pharmaceutical synthesis, and polymer chemistry highlight its significance in advancing chemical processes and material science.

References

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DOI: 10.1007/s00726-002-0403-8

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DOI: 10.1007/s00216-008-2496-8

2012. Facile Phase Transfer of Large, Water-Soluble Metal Nanoparticles to Nonpolar Solvents. Langmuir.
DOI: 10.1021/la2038894