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1122-58-3

Basic Information
CAS No.: 1122-58-3
Name: 4-Dimethylaminopyridine
Molecular Structure:
Molecular Structure of 1122-58-3 (4-Dimethylaminopyridine)
Formula: C7H10N2
Molecular Weight: 122.17
Synonyms: Pyridine, 4-(dimethylamino)-;N,N-Dimethylpyridin-4-amine;4-Pyridinamine, N,N-dimethyl-;N,N-dimethyl-1H-pyridin-4-amine;4-(Dimethylamino)pyridine;p-Dimethylaminopyridine;4-Dimethylamino-pyridine(DMAP);4-Dimethylaminopyridine(DMAP);gamma-(Dimethylamino)pyridine;4-Pyridinamine,N,N-dimethyl-;DMAP (catalyst);4-Dimethylamino pyridine;4-(Dimethylamino) Pyridine;DMAP 4-Dimethylaminopyridine;4-Dimethylaminopy ridine;4-Dimethyl aminopyridine;4-Dimethylaminopyridine DMAP;4-Di(methylamino)pyridine;4-Dimethylamino-pyridine;DMAP (4-Dimethylaminopyridine);4-Dimethylaminopyridine (dmap);4-DMAP;4-Dimethyl amino pyridine;N4,N4-Dimethylpyridin-4-amine;4-(N,N-Dimethylamino)pyridine;
EINECS: 214-353-5
Density: 1.012 g/cm3
Melting Point: 83-86 °C(lit.)
Boiling Point: 194.9 °C at 760 mmHg
Flash Point: 71.7 °C
Solubility: miscible with water
Appearance: white to yellow crystalline powder
Hazard Symbols: ToxicT,CorrosiveC,VeryT+
Risk Codes: 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25
Safety: 36/37/39-45-28A-26-28-36/37-53-27-22
Transport Information: UN 2811 6.1/PG 2
PSA: 16.13000
LogP: 1.14760
Synthetic route
100-48-1

pyridine-4-carbonitrile

124-40-3

dimethyl amine

Conditions
ConditionsYield
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid at 90℃; for 1.5h; Inert atmosphere;
Stage #2: dimethyl amine at 70℃; for 2.5h; Inert atmosphere;
Stage #3: With sodium hydroxide at 70 - 90℃; for 3.5h; Temperature; Reagent/catalyst; Inert atmosphere;
99.4%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid In water at 70℃; for 4h; Inert atmosphere;
Stage #2: dimethyl amine In water at 50℃; for 3h; Temperature; Inert atmosphere;
99%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; hydroquinone; acrylic acid In water at 90℃; for 6h;
Stage #2: dimethyl amine In water for 3h; Temperature; Reflux;
98.6%
1005-31-8

4-(dimethylamino)pyridine N-oxide

Conditions
ConditionsYield
With bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate salt; potassium iodide In ethanol at 20℃; for 1h;95%
With phenylboronic acid In 1,2-dichloro-ethane at 120℃; for 10h;90%
With 1,1,1,2,2,2-hexamethyldisilane; tetrabutyl ammonium fluoride In tetrahydrofuran at 24 - 30℃; for 8h;84%
7379-35-3

4-chlorpyridine hydrochloride

124-40-3

dimethyl amine

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane at 70℃; under 6000480 Torr; for 20h; Substitution;93%

dimethyl amine

dimethyl amine

Conditions
ConditionsYield
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 25℃; for 24h; Inert atmosphere;90%

124-40-3

dimethyl amine

Conditions
ConditionsYield
In methanol at 40 - 45℃; for 4h; Autoclave;89.7%
3585-33-9

lithium dimethylamide

58815-96-6

diisopropyl pyridin-4-ylphosphonate

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine In toluene at -40 - 20℃; for 1.5h; Substitution;86%
67-56-1

methanol

1122-61-8

4-nitropyridine

Conditions
ConditionsYield
With aluminum (III) chloride; water In acetonitrile at 20℃; Irradiation;86%
With palladium 10% on activated carbon; potassium tert-butylate at 150℃; for 48h;
15854-87-2

4-iodopyridine

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;82%
7379-35-3

4-chlorpyridine hydrochloride

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With ammonia In water at 240℃; for 0.5h;78%
626-61-9

4-Chloropyridine

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium carbonate at 80℃; for 10h;75%
for 34h; Reflux; neat (no solvent);69%
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;21 %Spectr.
1120-87-2

4-bromopyridin

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;73%

dmap

dmap

Conditions
ConditionsYield
Stage #1: C9H8N2O2; dimethyl amine In water at 45℃; for 0.25h;
Stage #2: With sodium hydroxide In water at 70℃; for 1 - 2h;
67.1%
1121-58-0

4-(Methylamino)pyridine

67-56-1

methanol

Conditions
ConditionsYield
With rhodium(III) chloride hydrate; potassium tert-butylate at 130℃; for 48h; Sealed tube; High pressure;66%
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

68-12-2, 33513-42-7

N,N-dimethyl-formamide

Conditions
ConditionsYield
Stage #1: 1-(4-pyridyl)pyridinium chloride hydrochloride; N,N-dimethyl-formamide at 150 - 155℃; for 2 - 3h;
Stage #2: With sodium hydroxide In water at 20℃; pH=10 - 12;
65.05%
Stage #1: 1-(4-pyridyl)pyridinium chloride hydrochloride; N,N-dimethyl-formamide at 150 - 155℃; for 2 - 3h;
Stage #2: With sodium hydroxide In water at 20℃; pH=10 - 12;
65.05%

Conditions
ConditionsYield
In water51%

A

B

5028-28-4

N4,N4-dimethylpyridine-3,4-diamine

C

114474-08-7

2-amino-5-bromo-4-dimethylaminopyridine

Conditions
ConditionsYield
With potassium amide In diethyl ether; ammonia at -78 - -33℃; for 1.5h;A 40%
B 32%
C 10%
84539-35-5

(3-bromopyridin-4-yl)-dimethyl-amine

B

5028-28-4

N4,N4-dimethylpyridine-3,4-diamine

Conditions
ConditionsYield
With potassium amide In diethyl ether; ammonia at -78℃; for 0.0833333h;A 4%
B 31%
816-65-9

N-(1-ethoxyvinyl)-N,N-dimethylamine

290-38-0

1,2,4-triazine

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 12h;27%
504-24-5

4-aminopyridine

67-56-1

methanol

A

1121-58-0

4-(Methylamino)pyridine

Conditions
ConditionsYield
With aluminum oxide at 300 - 369℃;
4783-86-2

4-phenoxypyridine

506-59-2

N,N-dimethylammonium chloride

Conditions
ConditionsYield
at 180℃;

dmap

dmap

Conditions
ConditionsYield
With phenol at 180 - 190℃;
55277-36-6

4-(dimethylamino)pyridinium cation

114444-46-1

C14H13NO

B

124225-44-1

1-methyl-4-(phenylacetyl)pyridinium cation

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant;
130671-19-1

1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium; bromide

B

107-13-1

acrylonitrile

Conditions
ConditionsYield
With potassium hydroxide; potassium chloride In water at 25℃; Rate constant; var. basic media; pH dependence of the velocity const.;

1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium

B

107-13-1

acrylonitrile

Conditions
ConditionsYield
With potassium chloride; hydroxide In water at 25℃; Equilibrium constant;
135041-86-0

4-Dimethylamino-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide

B

100-13-0

4-nitrostyrene

Conditions
ConditionsYield
With potassium hydroxide; potassium chloride at 25℃; Rate constant;
96318-91-1

N-phenylbenzimidoyl-4-dimethylaminopyridinium chloride

A

93-98-1

N-phenyl benzoyl amide

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
101476-38-4

4-Dimethylamino-1-{[(Z)-phenylimino]-m-tolyl-methyl}-pyridinium; chloride

B

23099-05-0

3-methyl-N-phenylbenzamide

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
113399-37-4

1-{(3-Bromo-phenyl)-[(Z)-phenylimino]-methyl}-4-dimethylamino-pyridinium; chloride

A

B

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;

B

6833-23-4

3-methoxy-N-phenylbenzamide

Conditions
ConditionsYield
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 30℃;
With sodium hydroxide; sodium chloride In 1,4-dioxane; water at 25℃; Rate constant;
709-49-9

1-iodo-2,4-dinitrobenzene

111055-10-8

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; iodide

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
88-88-0

2,4,6-trinitrochlorobenzene

111055-14-2

4-Dimethylamino-1-(2,4,6-trinitro-phenyl)-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
4975-09-1

2,4-bis(trifluoromethylsulfonyl)chlorobenzene

111055-13-1

1-(2,4-Bis-trifluoromethanesulfonyl-phenyl)-4-dimethylamino-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
970-88-7

2,4-dinitrophenyl benzenesulfonate

111055-12-0

Benzenesulfonate4-dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium;

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
71153-92-9

N-Pentafluorophenyl(C-pentafluorophenyl)imidoyl chloride

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
99-81-0

4-Nitrophenacyl bromide

1-[2-(4-nitrophenyl)-2-oxoethyl]-4-(dimethylamino)pyridinium bromide

Conditions
ConditionsYield
In benzene for 0.166667h; Ambient temperature;100%
In acetone for 0.5h; Heating;90%
70-34-8

2,4-Dinitrofluorobenzene

111055-09-5

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; fluoride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
87228-28-2

N-(pentafluorophenyl)-benzimidoyl chloride

120703-73-3

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-phenyl-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium salts;100%
120703-72-2

2,3,4,5,6-Pentafluoro-N-phenyl-benzimidoyl chloride

120703-76-6

4-Dimethylamino-1-{pentafluorophenyl-[(Z)-phenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium chloride;100%
120703-70-0

4-Methyl-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride

120703-74-4

4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-p-tolyl-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
120703-71-1

4-Nitro-N-(2,3,4,5,6-pentafluoro-phenyl)-benzimidoyl chloride

120703-75-5

4-Dimethylamino-1-{(4-nitro-phenyl)-[(Z)-pentafluorophenylimino]-methyl}-pyridinium; chloride

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Mechanism;100%
97-00-7

1-chloro-2,4-dinitro-benzene

110465-52-6

4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; chloride

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
3764-01-0

2,4,6-trichloropyrimidine

143-66-8

sodium tetraphenyl borate

1,1',1''-(pyrimidin-2,4,6-triyl)-tris-4-dimethylaminopyridinium tris(tetraphenylborate)

Conditions
ConditionsYield
In ethyl acetate Ambient temperature;100%
In ethyl acetate100%
2176-62-7

2,3,4,5,6-pentachloropyridine

1-(4-dimethylamino)-[2,3,5,6-tetrachloro-pyridin-4-yl]pyridinium chloride

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 80℃; for 3h;100%
In 1,2-dichloro-benzene at 60℃;87%
In 1,2-dichloro-benzene at 80 - 90℃;
2176-62-7

2,3,4,5,6-pentachloropyridine

(3,5-dichloropyridine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] trichloride

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 120℃; for 3h;100%
In 1,2-dichloro-benzene Heating;
Heating;
111-83-1

1-bromo-octane

4-(dimethylamino)-1-octylpyridinium bromide

Conditions
ConditionsYield
In acetonitrile for 15h; Heating;100%
In acetone for 9h; Heating;50%
In ethyl acetate at 70℃; for 48h;

C58H72N10(2+)*2Cl(1-)

Conditions
ConditionsYield
In methanol for 24h; Heating;100%
864950-69-6

methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester

4-dimethylamino-1-[3-(2-phenylethynyl-phenyl)-prop-2-ynyl]-pyridinium; methanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
2,4-dinitrophenyl benzoate

2,4-dinitrophenyl benzoate

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 25℃; Kinetics;100%

4-dimethylaminophenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(iodide)

4-dimethylaminophenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(iodide)

Conditions
ConditionsYield
In chlorobenzene for 24h; Heating;100%
2,4-dihydroxyphenylazopentafluorobenzene

2,4-dihydroxyphenylazopentafluorobenzene

27607-77-8

trimethylsilyl trifluoromethanesulfonate

2,4-dihydroxyphenylazopentakis[4-(dimethylamino)-1-pyridinio]benzene pentakis(triflate)

Conditions
ConditionsYield
In chlorobenzene for 24h; Heating;100%
27607-77-8

trimethylsilyl trifluoromethanesulfonate

N-[4-(dimethylamino)phenyl]-1-(2',3',4',5',6'-pentafluorophenyl)methanimine

4-dimethylaminobenzaldehyde pentakis[4-(dimethylamino)-1-pyridinio]phenylimine pentakis(triflate)

Conditions
ConditionsYield
In chlorobenzene for 48h; Heating;100%
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    CAS:1122-58-3 4-Dimethylaminopyridine

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    Molecular Formula C7H10N2 Molecular Weight 122.17 CAS Registry Number 1122-58-3 EINECS 214-353-5 Appearance:white crystalline power Content:≥99.0% MP:110.0-111.5℃ Residues after lgnition:0.25% Los

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    Product Description Product name 4-Dimethylaminopyridine CAS 1122-58-3 Assay 99% Appearance White crystalline powder Capacity 500mt/year Min.package 1gram Standard

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    N-(4-Pyridyl)dimethylamine

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    4-Dimethylamino pyridine CAS No: 1122-58-3 Molecular formula:C7H10N2 Structural formula: Molecular weight: 122.17 Propertie : Appearance: light yellow or off-white crystal Melting point : 112-114°C Assay: ≥99.6% Moisture:≤0.5%

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Specification

The 4-Dimethylaminopyridine, with the CAS registry number 1122-58-3,is also known as N,N-Dimethylpyridin-4-amine; DMAP. It belongs to the product categories of Nucleotides;Amines;Aromatics. This chemical's molecular formula is C7H10N2 and molecular weight is 122.17.Its EINECS number is 214-353-5. What's more,Its systematic name is 4-(Dimethylamino)pyridine .It is a White solid which is stable,incompatible with acids,oxidizing agents. It is a highly efficient catalyst for acylation reactions.Its analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxilar type amides.

Physical properties about 4-Dimethylaminopyridine are:
(1)ACD/LogP:  1.34; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  -1.15; (4)ACD/LogD (pH7.4):  -0.63; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  1.00; (8)ACD/KOC (pH 7.4):  1.37; (9)#H bond acceptors:  2; (10)#H bond donors:  0; (11)#Freely Rotating Bonds:  1; (12)Index of Refraction:  1.554; (13)Molar Refractivity:  38.658 cm3; (14)Molar Volume:  120.648 cm3;(15)Surface Tension:  40.0180015563965 dyne/cm; (16)Density:  1.013 g/cm3; (17)Flash Point:  71.687 °C; (18)Enthalpy of Vaporization:  43.112 kJ/mol; (19)Boiling Point:  194.922 °C at 760 mmHg; (20)Vapour Pressure:  0.430999994277954 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:n1ccc(N(C)C)cc1;
(2)Std. InChI:InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3;
(3)Std. InChIKey:VHYFNPMBLIVWCW-UHFFFAOYSA-N.

Preparation of 4-Dimethylaminopyridine :
4-Dimethylaminopyridine can be prepared in a two-step procedure from pyridine, which is first oxidized to 4-pyridylpyridinium cation. This cation then reacts with dimethylamine:


Safety Information of 4-Dimethylaminopyridine:
The 4-Dimethylaminopyridine is toxic by inhalation, in contact with skin and if swallowed and Irritating to eyes, respiratory system and skin. It is harmful by inhalation. And it may cause harm to the unborn child. There is limited evidence of a carcinogenic effect. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .When you use it wear suitable protective clothing, gloves and eye/face protection. Avoid exposure - obtain special instructions before use. After contact with skin, wash immediately with plenty of soap-suds. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And take off immediately all contaminated clothing.

The toxicity data of 4-Dimethylaminopyridine as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04228,
mouse LDLo oral 470mg/kg (470mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 14, Pg. 111, 1985.
rabbit LD50 skin 13mg/kg (13mg/kg)   National Technical Information Service. Vol. OTS0536502,
rat LD50 oral 250mg/kg (250mg/kg)   National Technical Information Service. Vol. OTS0536502,