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4-Pyrrolidinopyridine
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Name

4-Pyrrolidinopyridine

 EINECS 219-534-2
CAS No. 2456-81-7 Density 1.08 g/cm3
PSA 16.13000 LogP 1.74680
Solubility water: 3 g/L (21 °C) Melting Point 57-58 °C
Formula C9H12N2 Boiling Point 263.1 °C at 760 mmHg
Molecular Weight 148.208 Flash Point 142 °C
Transport Information UN 2923 8/PG 3 Appearance white crystal
Safety 26-36/37/39-45 Risk Codes 25-34-41-23/24/25
Molecular Structure Molecular Structure of 2456-81-7 (4-Pyrrolidinopyridine) Hazard Symbols ToxicT
Synonyms

4-Pyrrolidin-1-ylpyridine;Pyridine, 4-(1-pyrrolidinyl)-;4-(Pyrrolidin-1-yl)pyridine;4-pyrrolidin-1-yl-1H-pyridine;4-(1-Pyrrolidinyl)pyridine;4-(Pyrrolidin-1-yl)piperidine;

Article Data 23

4-Pyrrolidinopyridine Synthetic route

123-75-1

pyrrolidine

7379-35-3

4-chlorpyridine hydrochloride

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
With sodium hydroxide; water In 1,4-dioxane at 70℃; under 6000480 Torr; for 20h; Substitution;90%
With sodium hydride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; tert-butyl alcohol; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 65℃; for 2.5h;90%
In water at 130℃; for 0.5h; Microwave irradiation;90%
With copper; caesium carbonate; methyl-alpha-D-glucopyranoside In water; dimethyl sulfoxide at 110℃; for 14h; Sealed tube; Green chemistry;89%
at 130℃; for 0.5h; microwave irradiation;85%
123-75-1

pyrrolidine

626-61-9

4-Chloropyridine

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
With zinc(II) nitrate hexahydrate In acetonitrile at 75℃; for 24h; Sealed tube; Green chemistry;89%
With potassium phosphate; benzoin oxime; copper diacetate In dimethyl sulfoxide at 80℃; Inert atmosphere;86%
at 130℃; for 0.5h; microwave irradiation;85%
121409-81-2

N-Pyridin-4-yl-succinamic acid methyl ester; hydrochloride

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 9h; Heating;58%
123-75-1

pyrrolidine

626-55-1

3-Bromopyridine

A

69698-09-5

N-(pyridine-3-yl)pyrrolidine

B

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
With sodium amide; sodium t-butanolate 1) THF, 40 deg C, 2 h 2) 40 deg C, 4.7 h; Yield given. Multistep reaction. Yields of byproduct given;
123-75-1

pyrrolidine

27248-04-0

4-((trimethylsilyl)oxy)pyridine

15097-49-1

N-trimethylsilylpyrrolidine

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
With ammonium sulfate In pyridine at 150℃; for 15h; Yield given;
108-96-3

4-pyridone

15097-49-1

N-trimethylsilylpyrrolidine

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
In pyridine at 150 - 160℃; 1) 6 h; 12 h, 2) 40 h; Yield given;
123-75-1

pyrrolidine

100-48-1

pyridine-4-carbonitrile

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
Stage #1: pyrrolidine With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.25h;
Stage #2: pyridine-4-carbonitrile With cesium fluoride In tetrahydrofuran; hexane at 65℃; for 2h; Further stages.;		80 % Chromat.
504-24-5

4-aminopyridine

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / diethyl ether; tetrahydrofuran / 1 h / Heating
2: 58 percent / 10M Me2S*BH3 / tetrahydrofuran / 9 h / Heating
View Scheme
626-64-2

pyridin-4-ol

337913-25-4

phosphorus pentaoxide

A

5683-33-0

2-(Dimethylamino)pyridine

B

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
In dibutylamine
In dibutylamine
1349883-23-3

C33H49BrN2Si

A

1349883-19-7

(E)-1,2-dibromo-1,2-bis(1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacen-4-yl)disilene

B

2456-81-7

4-pyrrolidin-1-ylpyridine

Conditions
ConditionsYield
In benzene-d6 at 25℃; Equilibrium constant;

4-Pyrrolidinopyridine Specification

The 4-Pyrrolidinopyridine with CAS registry number of 2456-81-7 is also known as Pyridine, 4-(1-pyrrolidinyl)-. The IUPAC name is 4-Pyrrolidin-1-ylpyridine. It belongs to product categories of Pyridine; Pyridines derivates; Pyridines; Condensation & Active Esterification; Synthetic Organic Chemistry; C9 to C46; Heterocyclic Building Blocks. Its EINECS registry number is 219-534-2. In addition, the formula is C9H12N2 and the molecular weight is 148.21. This chemical is a white crystal and should be stored in sealed containers in cool, dry place and away from oxidizing agents.

Physical properties about 4-Pyrrolidinopyridine are: (1)ACD/LogP: 1.43; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.06; (4)ACD/LogD (pH 7.4): -0.59; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (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: 1.562; (13)Molar Refractivity: 44.54 cm3; (14)Molar Volume: 137.1 cm3; (15)Surface Tension: 45.4 dyne/cm; (16)Density: 1.08 g/cm3; (17)Flash Point: 112.9 °C; (18)Enthalpy of Vaporization: 50.1 kJ/mol; (19)Boiling Point: 263.1 °C at 760 mmHg; (20)Vapour Pressure: 0.0105 mmHg at 25 °C.

Preparation of 4-Pyrrolidinopyridine: it is prepared by reaction of pyrrolidine with 4-chloro-pyridine; hydrochloride. The reaction needs reagents 1,3-bis(2,4,6-trimethyl)-dihydroimidazolium chloride, NaH, t-BuOH, catalyst Ni(acac)2 and solvent tetrahydrofuran at 65 °C for 2.5 hours. The yield is about 90%.

4-Pyrrolidinopyridine is prepared by reaction of pyrrolidine with 4-chloro-pyridine; hydrochloride.

Uses of 4-Pyrrolidinopyridine: it is used as catalyst for polymerization, esterification. What's more, it can be used as ligand of metal complexes.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. Besides, it is toxic by inhalation, in contact with skin and if swallowed. This chemical has risk of serious damage to eyes and may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If accident happens or you feel unwell seek medical advice immediately

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1CCN(C1)C2=CC=NC=C2
2. InChI: InChI=1S/C9H12N2/c1-2-8-11(7-1)9-3-5-10-6-4-9/h3-6H,1-2,7-8H2
3. InChIKey: RGUKYNXWOWSRET-UHFFFAOYSA-N

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