4-(Dimethylamino)pyridine

• Catalog No.: A13016
• CAS Number: 1122-58-3
• M. F.: C7H10N2
• M. W.: 122.1677
• Purity: 99%

SYNONYMS

• Title: 4-二甲基氨基吡啶
• IUPAC name: N,N-dimethylpyridin-4-amine
• IUPAC Traditional name: 4-dimethylaminopyridine

DATABASE IDS

• MDL Number: MFCD00006418
• Beilstein Number: 110354
• EC Number: 214-353-5
• CAS Number: 1122-58-3

PROPERTIES

• Purity: 99%
• Boiling Point: 162°C/50mm
• Flash Point: 124°C(255°F)
• Melting Point: 110-113°C
• GHS Hazard statements: H301-H310-H314-H318
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A
• Risk Statements: 22-27-34
• RTECS: US9230000
• Safety Statements: 26-27/28-36/37/39-45-60
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2928
• Packing Group: I

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 ?-keto esters in toluene: J. Org. Chem., 50, 3618 (1985), and for smooth decarboalkoxylation of enolizable ?-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).