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

A13016 4-(Dimethylamino)pyridine, 99%

CAS Number
1122-58-3
Synonyms

Size Price ($) Quantity Availability
5g 13.29
25g 44.10
100g 126.69
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4-(Dimethylamino)pyridine, 99%

MDL
MFCD00006418
EINECS
214-353-5

Chemical Properties

Formula
C7H10N2
Formula Weight
122.17
Melting point
110-113°
Boiling Point
162°/50mm
Flash Point
124°(255°F)
Solubility
Soluble in methanol, benzene, ethyl acetate, chloroform, methylene chloride, acetone, and acetic acid. Slightly soluble in ether, diisopropyl ether, cyclohexane, hexane, and water.

Applications

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.

Notes

Incompatible with strong oxidizing agents and strong acids.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H310-H314-H318

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

Precautionary Statements: 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.

Other References

Beilstein
110354
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2933.39
TSCA
Yes
RTECS
US9230000

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