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1122-58-3

Basic Information
CAS No.: 1122-58-3
Name: 4-Dimethylaminopyridine
Article Data: 109
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.
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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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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,