N,N-dimethylpyridin-4-amine

• ChemBase ID: 8556
• Molecular Formular: C7H10N2
• Molecular Mass: 122.1677
• Monoisotopic Mass: 122.08439833
• SMILES: c1cc(ccn1)N(C)C
• Canonical SMILES: CN(c1ccncc1)C
• InChI: InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3
• InChIKey: VHYFNPMBLIVWCW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethylpyridin-4-amine
• IUPAC Systematic name: 4-(dimethylamino)azine; N,N-dimethyl-4-aminoazine; 4-(dimethylamino)azabenzene; N,N-dimethyl-4-aminoazabenzene
• IUPAC Traditional name: 4-dimethylaminopyridine
• Synonyms: 4-Dimethylaminopyridine; N,N-dimethylpyridin-4-amine; 4-(dimethylamino)pyridine; N,N-dimethyl-4-aminopyridine; 4-DIMETHYLAMINO PYRIDINE; N,N-Dimethylpyridin-4-amine; DMAP; 4-(Dimethylamino)pyridine; ChemDose™, 4-(Dimethylamino)pyridine impregnated tablets; DMAP, ChemDose™ impregnated tablets; 4-(Dimethylamino)pyridine, ChemDose™ tablets; DMAP solution; 4-(Dimethylamino)pyridine solution; 4-(Dimethylamino)pyridine; ChemDose™，4-(二甲氨基)吡啶浸渍片剂; DMAP，ChemDose™ 浸渍片剂; 4-(二甲氨基)吡啶，ChemDose™ 片剂; DMAP 溶液; 4-(二甲氨基)吡啶 溶液; 4-(二甲氨基)吡啶; 4-二甲基氨基吡啶

Database IDs

• CAS Number: 1122-58-3
• EC Number: 214-353-5
• MDL Number: MFCD00006418
• Beilstein Number: 110354; 3539759
• PubChem SID: 24874123; 24874122; 24846774; 160971863; 24864562
• PubChem CID: 14284
• Chemspider ID: 13646
• Wikipedia Title: 4-Dimethylaminopyridine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -0.11969553
• LogD (pH = 7.4): 0.008813705
• Log P: 0.86361724
• Molar Refractivity: 38.3297 cm^3
• Polarizability: 14.25138 Å^3
• Polar Surface Area: 16.13 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble0.1 g/mL, clear; methanol: soluble0.1 g/mL, clear, colorless to almost colorless
• Apperance: prilled; white to off-white
• Melting Point: 108-110 °C(lit.); 110-113 °C; 110-113°C; 110-113°C; 111-114 °C; 112°C; 112-114°C
• Boiling Point: 162 °C at 50 mmHg; 162°C/50mm; 162°C/50mm
• Flash Point: 0 °F; 110 °C; 124°C; 124°C(255°F); -18 °C; 230 °F; 25 °F; -4 °C
• Density: 0.884 g/mL at 25 °C; 0.906 g/mL at 25 °C
• Refractive Index: n20/D 1.384; n20/D 1.417

Safety Information

• Storage Warning: TOXIC; Very Toxic/Corrosive/Light Sensitive/Store under Argon
• RTECS: US9230000
• European Hazard Symbols: Corrosive (C); Flammable (F); Toxic (T); Highly toxic (T+)
• UN Number: 1992; 2811; UN2928
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 1; 2; I
• Risk Statements: 11-22-27-36/37; 11-22-27-36-66-67; 22-27-34; 25-27-36/37/38; 25-27-36/37/38-40; R:22-27-34
• Safety Statements: 16-26-28.1; 16-26-28.1-29-33-36/37/39-45; 26-27/28-36/37/39-45-60; 26-28-36/37/39-45; 26-28-36/37-45; S:27/28-29-36/37/39-45
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H314-H318; H301-H310-H315-H319-H335; H302-H310-H315-H319-H335-H351
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P280-P301 + P310-P302 + P350-P305 + P351 + P338-P310; P261-P280-P302 + P350-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1992 3/PG 2; UN 2811 6.1/PG 1

Product Information

• Purity: ≥98.0% (NT); ≥99%; ≥99.0% (NT); 98%; 99%
• Concentration: 0.5 M in ethyl acetate; 0.5 M in THF
• Grade: puriss.; purum; ReagentPlus®
• Empirical Formula (Hill Notation): C7H10N2

DETAILS

Sigma Aldrich - 29224

Application
A highly efficient catalyst for acylation reactions

Sigma Aldrich - 39405

Application
A highly efficient catalyst for acylation reactions
Other Notes
Hypernucleophilic acylation catalyst. Review1,2,3

Sigma Aldrich - 700169

Legal Information
Covered by International Patent Application No. PCT/DK05/000428 and related patent applications, including European Patent Application No. 05753717.7.
ChemDose is a trademark of Reaxa Ltd.

Sigma Aldrich - 714720

Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 522821

Application
A highly efficient catalyst for acylation reactions
Packaging
100, 500 g in glass bottle
Legal Information
A product of Reilly Industries, Inc.
Quality
Low dusting, free-flowing

Sigma Aldrich - 107700

Application
A highly efficient catalyst for acylation reactions
Used in conjunction with TiCl4 in a Claisen condensation between ketene silyl acetals and carboxylic acids leading to β-keto esters.
Packaging
5, 25, 100, 500 g in glass bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 714844

Packaging
100 mL in Sure/Seal™

Sigma Aldrich - 522805

Application
A highly efficient catalyst for acylation reactions
Packaging
5 g in glass bottle

Sigma Aldrich - D5640

Application
酰化反应的高效催化剂

MP Biomedicals - 05222621

MP Biomedicals Rare Chemical collection

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).