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1122-58-3 - 4-(Dimethylamino)pyridine, 99% - A13016 - Alfa Aesar

A13016 4-(Dimethylamino)pyridine, 99%

Numéro CAS

Dimensions Prix ($) Quantité Disponibilité
5g 15,30
25g 44,20
100g 128,00
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4-(Dimethylamino)pyridine, 99%


Propriétés chimiques

Poids formulaire
Point de fusion
Point d'ébullition
Point d'éclair
Soluble in methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. Slightly soluble in ether, diisopropyl ether, cyclohexane, hexane, and water.


4-(Dimethylamino)pyridine is a useful nucleophilic catalyst for various reactions viz. esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation and Steglich rearrangement. It is also an effective catalyst for transesterification of beta-keto esters and silylation of alcohols.


Incompatible with strong oxidizing agents and strong acids.

Références bibliographiques

Hypernucleophilic catalyst. Greatly accelerates the acylation of hindered, including tertiary, alcohols; reviews: Angew. Chem. Int. Ed., 17, 569 (1978). Chem. Soc. Rev., 12, 129 (1983). Catalyst for acylation of alcohols using mixed anhydrides of hindered carboxylic acids with methanesulfonic acid: Synth. Commun., 12, 727 (1982), and with mixed carboxylic anhydrides: J. Org. Chem., 50, 560 (1985). In the Yamaguchi method of macrocyclic lactonization the mixed anhydride formed with 2,4,6-Trichlorobenzoyl­ chloride, L14159 is cyclized with 2 equiv. of DMAP; high dilution conditions are not required: Bull. Chem. Soc. Jpn., 52, 1989 (1979). For improved method in a high yield synthesis of erythronolide A, see: J. Org. Chem., 55, 7 (1990).

Greatly increases the rate of ester and thio ester formation in the carbodiimide method of coupling (Steglich esterification): Angew. Chem. Int. Ed., 17, 522 (1978). For similar use in macrolactonizations, see: J. Org. Chem., 50, 2394 (1985), and in carbodiimide peptide coupling reactions: Int. J. Pept. Prot. Res., 18, 459 (1981). For peptide reagents, see Appendix 6.

Effective catalyst for transesterification of ß-keto esters in toluene: J. Org. Chem., 50, 3618 (1985), and for smooth decarboalkoxylation of enolizable ß-keto esters in toluene containing a small amount of water: J. Org. Chem., 54, 3474 (1989). Under these conditions, other bases (N,N-dimethylaniline, pyridine, tetra-n-pentylammonium bromide) are ineffective.

Also useful as a catalyst for various alkylations. For use in formation of trityl ethers, see: Tetrahedron Lett., 95, (1979); extension to mono- and di-methoxytrityl ethers: Tetrahedron Lett., 21, 3899 (1980); J. Org. Chem., 47, 571 (1982); Chem. Lett., 15 (1982); J. Am. Chem. Soc., 104, 1316 (1982). Useful in silylation of alcohols to give TBDMS ethers: Tetrahedron Lett., 99, (1979).

Catalyst in a simple preparation of N-Boc-amides, using Di-tert-butyl­ dicarbonate, A14708: Acta Chem. Scand. B, 40, 745 (1986); and also of N-Boc-pyrroles: Org. Synth. Coll., 9, 121 (1998).

Reacts with thionyl chloride to form the chlorosulfinyl chloride, an effective reagent for the conversion of acids to their acid chlorides: Synth. Commun., 12, 1139 (1982), and for the dehydration of aldoximes to nitriles: Synthesis, 472 (1983).

For a brief feature on the uses of this reagent in synthesis, see: Synlett, 1568 (2003). Review of developments in the search for optimal reactivity and selectivity with 4-(dialkylamino)pyridines: Angew. Chem. Int. Ed., 43, 5436 (2004).

Xue, F.; Liu, Z.; Wan, N.; Zhu, H.; Zheng, Y. Engineering the epoxide hydrolase from Agromyces mediolanus for enhanced enantioselectivity and activity in the kinetic resolution of racemic epichlorohydrin. RCS Adv. 2015, 5 (40), 31525-31532.

Dobkowski, J.; Kijak, M.; Sazanovich, I. V.; Waluk, J. Solvent-Controlled Excited State Relaxation Path of 4-Acetyl-4'-(dimethylamino)biphenyl. J. Phys. Chem. B 2015, 119 (24), 7294-7307.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H301-H310-H314-H318

Toxic if swallowed. Fatal in contact with skin. Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P260-P262-P301+P310-P303+P361+P353-P305+P351+P338-P361-P301+P330+P331-P302+P350-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. Do NOT induce vomiting. IF ON SKIN: Gently wash with plenty of soap and water. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

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