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4-(Dimethylamino)pyridine

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Identification
Molecular formula
C7H10N2
CAS number
1122-58-3
IUPAC name
N,N-dimethylpyridin-4-amine
State
State

At room temperature, 4-(Dimethylamino)pyridine is typically a solid. It has a characteristic odor and is often used in organic synthesis as a nucleophilic catalyst.

Melting point (Celsius)
111.00
Melting point (Kelvin)
384.15
Boiling point (Celsius)
154.00
Boiling point (Kelvin)
427.15
General information
Molecular weight
122.17g/mol
Molar mass
122.1690g/mol
Density
0.9780g/cm3
Appearence

4-(Dimethylamino)pyridine, often abbreviated as DMAP, appears as a white to slightly yellow crystalline solid. It is often encountered in its solid form suitable for laboratory use.

Comment on solubility

Solubility of N,N-dimethylpyridin-4-amine

N,N-dimethylpyridin-4-amine, with the chemical formula C7H10N, exhibits interesting solubility characteristics that reflect its molecular structure and functional groups. The solubility of this compound can be summarized as follows:

  • Polar Characteristics: The presence of the amine group (-NH2) contributes to its polar nature, enhancing its solubility in polar solvents.
  • Water Solubility: N,N-dimethylpyridin-4-amine is moderately soluble in water due to hydrogen bonding capabilities.
  • Solvent Compatibility: This compound shows better solubility in organic solvents such as ethanol and acetone, making it versatile for various applications.

Overall, the solubility of N,N-dimethylpyridin-4-amine can be described as moderate, influenced by both the hydrophilic amine group and the hydrophobic pyridine ring. As a key point, it is essential to note that solubility can also be affected by factors such as temperature and the presence of other solutes in the solution.

Interesting facts

Interesting Facts about N,N-Dimethylpyridin-4-amine

N,N-Dimethylpyridin-4-amine, often abbreviated as DMAP, is a notable compound in organic chemistry. It is frequently utilized as a nucleophilic catalyst in various reactions, making it an invaluable asset in synthetic organic chemistry. Here are some intriguing aspects of this compound:

  • Catalytic Properties: DMAP is particularly effective in acylation reactions, where it helps facilitate the formation of amides and esters. Its ability to enhance reaction rates is widely recognized.
  • Mechanistic Insights: The mechanism by which DMAP operates involves its basic nitrogen atom, which can stabilize reactive intermediates, thus accelerating the transformation of substrates. Understanding this mechanism is crucial for chemists looking to optimize reaction conditions.
  • Flexibility in Applications: Beyond acylation, DMAP finds applications in a variety of chemical transformations, including alkylation, hydroxylation, and other nucleophilic substitutions. This versatility makes it a favorite among synthetic chemists.
  • Structural Influence: The presence of the 4-amino group in DMAP’s structure plays a significant role in its reactivity and selectivity. The spatial arrangement of the dimethyl groups and the pyridine ring contribute to its unique catalytic properties.
  • Environmental Considerations: As research intensifies in green chemistry, DMAP is regarded as a potential candidate for sustainable practices due to its efficiency and ability to function under mild conditions, reducing the need for harsh reagents.

In conclusion, N,N-dimethylpyridin-4-amine stands out not just for its utility but also for the insights it provides into catalytic mechanisms and synthetic strategies. As chemists continue to explore its capabilities, DMAP remains a significant compound in advancing chemical methodologies.

Synonyms
4-Dimethylaminopyridine
1122-58-3
N,N-Dimethylpyridin-4-amine
4-(Dimethylamino)pyridine
4-Pyridinamine, N,N-dimethyl-
N,N-Dimethyl-4-aminopyridine
CCRIS 6176
4-Dimethylaminepyridine
4-Dimethylaminopyridine (DMAP)
UNII-PFP1R6P0S8
EINECS 214-353-5
PFP1R6P0S8
BRN 0110354
DTXSID0044369
4(dimethylamino)pyridine
4-DMAP
DTXCID8024369
5-22-09-00112 (Beilstein Handbook Reference)
4-[dimethylamino]pyridine
VALACICLOVIR HYDROCHLORIDE IMPURITY G [EP IMPURITY]
VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY G [EP IMPURITY]
VALACICLOVIR HYDROCHLORIDE IMPURITY G (EP IMPURITY)
VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY G (EP IMPURITY)
pDimethylaminopyridine
N,NDimethyl4pyridinamine
N,NDimethylpyridin4amine
gamma(Dimethylamino)pyridine
4Pyridinamine, N,Ndimethyl
Pyridine, 4(dimethylamino)
4-dmap (tn)
inchi=1/c7h10n2/c1-9(2)7-3-5-8-6-4-7/h3-6h,1-2h
vhyfnpmblivwcw-uhfffaoysa-n
dmap
p-Dimethylaminopyridine
N,N-DIMETHYL-4-PYRIDINAMINE
N-(4-Pyridyl)dimethylamine
Pyridine, 4-(dimethylamino)-
4-dimethylamino-pyridine
887925-31-7
4-(dimethylamino)-pyridine
MFCD00006418
4-(dimethylamino) pyridine
dimethyl-pyridin-4-yl-amine
CHEMBL3561645
PYRIDINE, 4-DIMETHYLAMINO-
N,N-dimethyl-N-(4-pyridinyl)amine
4-DIMETHYLAMINO PYRIDINE
gamma-(Dimethylamino)pyridine
4-dimethylaminopyridin
dimethyl-4-pyridylamine
dimethylpyridin-4-ylamine
4-(n,n-dimethylamino)pyridine
JGD
4dimethylaminopyridine
4-dimethlaminopyridine
4-dimethyaminopyridine
4-dimethylaminopridine
4-dimethylaminopyridme
4-dimethylammopyridine
4-dimetylaminopyridine
4-dimethlyaminopyridine
4-dimethylaminopiridine
4-dimethylaminopryidine
4-dimethylamino pyridin
4-dimetylamino-pyridine
Valaciclovir impurity G
4-dimethylarninopyridine
p-dimethylamino pyridine
p-dimethylamino-pyridine
4 -dimethylaminopyridine
4- dimethylaminopyridine
4-di methylaminopyridine
4-di-methylaminopyridine
4-dimethy-laminopyridine
4-dimethylamine pyridine
4-dimethylaminopyridine-
para-dimethylaminopyridine
4-(dimethyamino)pyridine
4-dimetylamino- pyridine
4(dimethylamino) pyridine
4-(dimethyiamino)pyridine
4-(dimethyl)aminopyridine
4-(dimethylamino)pryidine
4-di-methylamino-pyridine
4-dimethylamino- pyridine
SCHEMBL189
4-(dimethylarnino)pyridine
dimethyl-pyridin-4yl-amine
dimethylpyridin-4-yl-amine
p-(dimethylamino)-pyridine
DMAP [MI]
4- (dimethylamino)pyridine
4-(dimethlyamino)-pyridine
4-(dimethyl amino)pyridine
4-(dimethyl-amino)pyridine
n,n-dimethylpyridin-4-amin
p-N,N-dimethylaminopyridine
4-(Dimethylamino-)pyridine
4-(dimethyl amino) pyridine
4-(dimethyl-amino)-pyridine
N,N dimethyl-4-pyridinamine
N,N-dimethyl 4-pyridinamine
4-(Dimethylamino)- pyridine
N,N-Dimethy-4-aminopyridine
4(N,N dimethylamino)pyridine
4(N,N-dimethylamino)pyridine
n,n'-dimethyl-4-pyridinamine
N,N-dimethyl-4-pyridineamine
N,N-dimethylpyridine-4-amine
4-(N,N-dimethyamino)pyridine
4-(N,N-dimetylamino)pyridine
n,n-dimethyl-4-amino pyridine
N,N-dimethyl-pyridin-4-amine
N,N-dimethylpyridin -4-amine
4-(N,N-dimethyiamino)pyridine
4-(N,N-dimethyl)aminopyridine
N, N-dimethyl-4-aminopyridine
.gamma.-(Dimethylamino)pyridine
para-N,N-dimethylamino-pyridine
4-(n,n,-dimethylamino)pyridine
4-(n,n-dimethylamino)-pyridine
4-Dimethykaminopyridine (DMAP)
4-Dimethylaminopyridine, Prilled
4-(N, N-dimethylamino)pyridine
4-(N,N dimethylamino)-pyridine
4-(N,N'-dimethylamino)pyridine
4-(N,N-dimethyl amino)pyridine
4-(N,N-dimethyl-amino)pyridine
4-(N,N-dimethylamino) pyridine
N,N-dimethyl-pyridin-4-yl-amine
4-(N, N-dimethylamino) pyridine
4-(N, N-dimethylamino)-pyridine
4-(N,N'-dimethylamino) pyridine
CHEBI:182593
para-(N,N-dimethylamino) pyridine
(4-DMAP);4-Dimethylaminopyridine
4-(dimethylamino)pyridine (DMAP)
4-(Dimethylamino)pyridine; >99%
4--(N,N'-dimethylamino) pyridine
BCP26534
HY-Y1089
STR00352
DMAP;N,N'-Dimethyl-4-pyridinamine
Tox21_302184
BDBM50556493
CX1367
STK865133
AKOS000120170
CS-W008903
DMAP; N4,N4-Dimethylpyridin-4-amine
FD00992
PS-4600
SB40777
NCGC00257546-01
4-(N
AC-13385
BP-21319
DA-19672
DMAP pound>>N,N-Dimethylpyridin-4-amine
PD074147
4-(Dimethylamino)pyridine, prilled, 99%
CAS-1122-58-3
DB-016064
D1450
NS00008104
EN300-20577
A15124
AR-360/40355729
Q229897
4-(Dimethylamino)pyridine, purum, >=98.0% (NT)
4-(Dimethylamino)pyridine, ReagentPlus(R), >=99%
4-(Dimethylamino)pyridine, puriss., >=99.0% (NT)
F0001-0270
Z104478964
4-(Dimethylamino)pyridine, pharmaceutical impurity standard
4-Pyridinamine,N,N-dimethyl-, hydrobromide, hydrate (1:1:2)
Valaciclovir impurity G, European Pharmacopoeia (EP) Reference Standard
4-(Dimethylamino)pyridine, ChemDose(TM) tablets, Loading: 0.04 mmol tablet.