4-Dimethylaminopyridine supplier

Name
4-Dimethylaminopyridine
EINECS 214-353-5
CAS No. 1122-58-3
Article Data109
CAS DataBase
Density 1.012 g/cm³
Solubility miscible with water
Melting Point 83-86 °C(lit.)
Formula C₇H₁₀N₂
Boiling Point 194.9 °C at 760 mmHg
Molecular Weight 122.17
Flash Point 71.7 °C
Transport Information UN 2811 6.1/PG 2
Appearance white to yellow crystalline powder
Safety 36/37/39-45-28A-26-28-36/37-53-27-22
Risk Codes 25-34-24/25-36/37/38-27-36-24-20-61-40-23/24/25
Molecular Structure
Hazard Symbols T,C,T+
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;
PSA 16.13000
LogP 1.14760

Synthetic route

: 100-48-1
pyridine-4-carbonitrile

: 124-40-3
dimethyl amine

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

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

dimethyl amine: dimethyl amine

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
In methanol at 40 - 45℃; for 4h; Autoclave;	89.7%

: 3585-33-9
lithium dimethylamide

: 58815-96-6
diisopropyl pyridin-4-ylphosphonate

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

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

dmap: dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

Conditions	Yield
In water	51%

A

B: 5028-28-4
N4,N4-dimethylpyridine-3,4-diamine

C: 114474-08-7
2-amino-5-bromo-4-dimethylaminopyridine

Conditions

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

...Expand

: 84539-35-5
(3-bromopyridin-4-yl)-dimethyl-amine

A: 1122-58-3
dmap

B: 5028-28-4
N4,N4-dimethylpyridine-3,4-diamine

Conditions

Conditions	Yield
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

: 1122-58-3
dmap

Conditions

Conditions	Yield
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

B: 1122-58-3
dmap

Conditions

Conditions	Yield
With aluminum oxide at 300 - 369℃;

...Expand

: 4783-86-2
4-phenoxypyridine

: 506-59-2
N,N-dimethylammonium chloride

Conditions

Conditions	Yield
at 180℃;

dmap: dmap

Conditions

Conditions	Yield
With phenol at 180 - 190℃;

: 55277-36-6
4-(dimethylamino)pyridinium cation

: 114444-46-1
C14H13NO

A: 1122-58-3
dmap

B: 124225-44-1
1-methyl-4-(phenylacetyl)pyridinium cation

Conditions

Conditions	Yield
In water at 25℃; Equilibrium constant;

...Expand

: 130671-19-1
1-(2-Cyano-ethyl)-4-dimethylamino-pyridinium; bromide

A: 1122-58-3
dmap

B: 107-13-1
acrylonitrile

Conditions

Conditions	Yield
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

A: 1122-58-3
dmap

B: 107-13-1
acrylonitrile

Conditions

Conditions	Yield
With potassium chloride; hydroxide In water at 25℃; Equilibrium constant;

: 135041-86-0
4-Dimethylamino-1-[2-(4-nitro-phenyl)-ethyl]-pyridinium; bromide

A: 1122-58-3
dmap

B: 100-13-0
4-nitrostyrene

Conditions

Conditions	Yield
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

B: 1122-58-3
dmap

Conditions

Conditions	Yield
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

A: 1122-58-3
dmap

B: 23099-05-0
3-methyl-N-phenylbenzamide

Conditions

Conditions	Yield
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

Conditions	Yield
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;

A: 1122-58-3
dmap

B: 6833-23-4
3-methoxy-N-phenylbenzamide

Conditions

Conditions	Yield
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;

: 1122-58-3
dmap

: 709-49-9
1-iodo-2,4-dinitrobenzene

: 111055-10-8
4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; iodide

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 88-88-0
2,4,6-trinitrochlorobenzene

: 111055-14-2
4-Dimethylamino-1-(2,4,6-trinitro-phenyl)-pyridinium; chloride

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 4975-09-1
2,4-bis(trifluoromethylsulfonyl)chlorobenzene

: 111055-13-1
1-(2,4-Bis-trifluoromethanesulfonyl-phenyl)-4-dimethylamino-pyridinium; chloride

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 970-88-7
2,4-dinitrophenyl benzenesulfonate

: 111055-12-0
Benzenesulfonate4-dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium;

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 71153-92-9
N-Pentafluorophenyl(C-pentafluorophenyl)imidoyl chloride

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

Conditions

Conditions	Yield
In acetonitrile at 25℃; Rate constant; Mechanism;	100%

: 1122-58-3
dmap

: 99-81-0
4-Nitrophenacyl bromide

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

Conditions

Conditions	Yield
In benzene for 0.166667h; Ambient temperature;	100%
In acetone for 0.5h; Heating;	90%

: 1122-58-3
dmap

: 70-34-8
2,4-Dinitrofluorobenzene

: 111055-09-5
4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; fluoride

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 87228-28-2
N-(pentafluorophenyl)-benzimidoyl chloride

: 120703-73-3
4-Dimethylamino-1-{[(Z)-pentafluorophenylimino]-phenyl-methyl}-pyridinium; chloride

Conditions

Conditions	Yield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium salts;	100%

: 1122-58-3
dmap

: 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

Conditions	Yield
In acetonitrile at 25℃; Rate constant; Mechanism; presence of tetraethylammonium chloride;	100%

: 1122-58-3
dmap

: 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

Conditions	Yield
In acetonitrile at 25℃; Rate constant; Mechanism;	100%

: 1122-58-3
dmap

: 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

Conditions	Yield
In acetonitrile at 25℃; Rate constant; Mechanism;	100%

: 1122-58-3
dmap

: 97-00-7
1-chloro-2,4-dinitro-benzene

: 110465-52-6
4-Dimethylamino-1-(2,4-dinitro-phenyl)-pyridinium; chloride

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 1122-58-3
dmap

: 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

Conditions	Yield
In ethyl acetate Ambient temperature;	100%
In ethyl acetate	100%

...Expand

: 1122-58-3
dmap

: 2176-62-7
2,3,4,5,6-pentachloropyridine

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

Conditions

Conditions	Yield
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℃;

: 1122-58-3
dmap

: 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

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

: 1122-58-3
dmap

: 111-83-1
1-bromo-octane

: 4-(dimethylamino)-1-octylpyridinium bromide

Conditions

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

: 1122-58-3
dmap

: 500999-97-3, 442686-04-6
C44H52Cl2N6

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

Conditions

Conditions	Yield
In methanol for 24h; Heating;	100%

: 864950-69-6
methanesulfonic acid 3-(2-phenylethynyl-phenyl)-prop-2-ynyl ester

: 1122-58-3
dmap

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

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 24h;	100%

: 1122-58-3
dmap

2,4-dinitrophenyl benzoate: 2,4-dinitrophenyl benzoate

Conditions

Conditions	Yield
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

Conditions	Yield
In chlorobenzene for 24h; Heating;	100%

...Expand

2,4-dihydroxyphenylazopentafluorobenzene: 2,4-dihydroxyphenylazopentafluorobenzene

: 1122-58-3
dmap

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

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

Conditions

Conditions	Yield
In chlorobenzene for 24h; Heating;	100%

...Expand

: 1122-58-3
dmap

: 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

Conditions	Yield
In chlorobenzene for 48h; Heating;	100%

...Expand

4-Dimethylaminopyridine 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)	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,

Product Name

4-Dimethylaminopyridine

Synthetic route

4-Dimethylaminopyridine Specification

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