4-Dimethylaminopyridine

Description

4-(Dimethylamino)pyridine (DMAP) is a toxic, corrosive solid that is widely used as a nucleophilic catalyst in esterification, hydrosilylation, Bayliss–Hillman reactions, and many more. In 2001, G. C. Fu and co-workers showed that chiral derivatives of DMAP can be used for stereoselective catalysis. More recently,?D. Seidel and co-workers used DMAP and other inexpensive reagents in acylation reactions?to give products that can be enantiomerically resolved. DMAP is also a nucleophilic catalyst and can be used in a variety of different reactions.DMAP is used as a very efficient acyl transfer agent. Studies have shown that esterification of hindered alcohols via anhydrides can be increased by a factor of 10,000 using 4-aminopyridines such as DMAP.

Chemical properties

White solid

The Uses of 4-Dimethylaminopyridine

4-Dimethylaminopyridine (Valaciclovir EP Impurity G; Valacyclovir USP Related Compound G) is a highly efficient catalyst for acylation reactions.

The Uses of 4-Dimethylaminopyridine

A highly fluorescent adenosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3?5?phosphodiester linkage using an automated DNA synthesizer

The Uses of 4-Dimethylaminopyridine

4-Dimethylaminopyridine is a versatile hypernucleophilic acylation catalyst, it is used to improve the yield, reduce the reaction time, improving relaxation process conditions. Widely used in perfumes, dyes, pigments, pesticides, pharmaceuticals and polymer compounds and other fields. Also used as a catalyst for the synthesis of polyurethane, a curing agent and a blowing catalyst.

The Uses of 4-Dimethylaminopyridine

DMAP is a useful highly basic nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement.

The Uses of 4-Dimethylaminopyridine

In a wide variety of organic syntheses as a catalyst.

What are the applications of Application

4-Dimethylaminopyridine is a highly efficient catalyst for acylation reactions

Definition

ChEBI: 4-Dimethylaminopyridine is a dialkylarylamine and a tertiary amino compound.

Definition

4-Dimethylaminopyridine is a dialkylarylamine and a tertiary amino compound.

General Description

Valacyclovir Related Compound G, also called as 4-(Dimethylamino)pyridine (DMAP) is an excellent catalyst for acylation of hindered alcohols and in chemical transformations. It is highly nucleophilic in nature.

Hazard

4-Dimethylaminopyridine (4-DMAP) is readily absorbed through the skin and is highly toxic by skin absorption. It also causes skin and eye burns. All skin and eye contact and inhalation should be avoided. Appropriate OSHA/ MSHA-approved respirator, chemical-resistant gloves and impervious or disposable protective clothing should be worn. Work should be carried out in a chemical fume hood.

Flammability and Explosibility

Non flammable

Hazard

4-Dimethylaminopyridine is a strong skin and eye irritant; toxic if ingested; highly toxic if absorbed through the skin.

Solubility in organics

4-Dimethylaminopyridine can be soluble in methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. Less soluble in ether, diisopropyl ether, cyclohexane, hexane, and water.

Purification Methods

Recrystallise DMAP from toluene [Sadownik et al. J Am Chem Soc 108 7789 1986]. [Beilstein 22 V 112.] § A polystyrene supported version (PS-DMAP) is commercially available.