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2-Pyridylacetonitrile

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Name

2-Pyridylacetonitrile

EINECS 220-364-6
CAS No. 2739-97-1 Density 1.085 g/cm3
PSA 36.68000 LogP 1.14768
Solubility Miscible with water. Melting Point 23-25 °C
Formula C7H6N2 Boiling Point 232.1 °C at 760 mmHg
Molecular Weight 118.138 Flash Point 93.9 °C
Transport Information UN 3276 6.1/PG 3 Appearance COLORLESS YELLOW TO ORANGE TO BROWN LIQUID
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 2739-97-1 (2-Pyridylacetonitrile) Hazard Symbols IrritantXi
Synonyms

(2-Pyridinyl)acetonitrile;(Pyridyl-2-yl)acetonitrile;2-(2-Pyridyl)acetonitrile;2-(Cyanomethyl)pyridine;

Article Data 36

2-Pyridylacetonitrile Synthetic route

117504-08-2

α-phenylsulfonylpyridine-2-acetonitrile

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With zinc In ethanol; acetic acid for 1h; Ambient temperature;94%
372-48-5

2-fluoropyridine

75-05-8

acetonitrile

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With potassium hexamethylsilazane In toluene at 0 - 20℃;87%
773837-37-9

sodium cyanide

6959-47-3

2-chloromethylpyridine hydrochloride

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide for 2.5h; Heating;84%
In dimethyl sulfoxide at 40℃; for 2.5h;84%
5451-39-8

2-(pyridine-2-yl)acetamide

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube;81%
With 1,2-dichloro-ethane; sodium chloride; trichlorophosphate
109-04-6

2-bromo-pyridine

75-05-8

acetonitrile

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation;
Stage #2: 2-bromo-pyridine In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Alkylation;
69%
109-04-6

2-bromo-pyridine

928664-98-6

4-isoxazoleboronic acid pinacol ester

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water In dimethyl sulfoxide at 130℃; for 16h; Domino Suzuki coupling and fragmentation reaction; Inert atmosphere;65%
694-59-7

pyridine N-oxide

A

110-86-1

pyridine

B

142-08-5

2-Pyridone

C

2739-97-1

pyridine-2-acetonitrile

D

366-18-7

[2,2]bipyridinyl

E

109-97-7

pyrrole

Conditions
ConditionsYield
at 750 - 850℃; under 0.001 - 0.01 Torr; Product distribution; Mechanism;A 31%
B 4%
C 6%
D 7%
E n/a
109-09-1

2-chloropyridine

75-05-8

acetonitrile

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃;15%
151-50-8

potassium cyanide

6959-47-3

2-chloromethylpyridine hydrochloride

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With ethanol; potassium iodide
109-04-6

2-bromo-pyridine

75-05-8

acetonitrile

A

504-29-0

2-aminopyridine

B

2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.25h; Irradiation;A 16 % Chromat.
B 75 % Chromat.

2-Pyridylacetonitrile Specification

The 2-Pyridylacetonitrile, with the CAS registry number 2739-97-1 and EINECS registry number 220-364-6, has the systematic name of pyridin-2-ylacetonitrile. It belongs to the following product categories: Miscellaneous; Pyridines; Pyridine; C7 and C8; Heterocyclic Building Blocks. And the molecular formula of this chemical is C7H6N2.

The physical properties of 2-Pyridylacetonitrile are as following: (1)ACD/LogP: -0.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.05; (4)ACD/LogD (pH 7.4): -0.04; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.45; (8)ACD/KOC (pH 7.4): 22.57; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 36.68 Å2; (13)Index of Refraction: 1.533; (14)Molar Refractivity: 33.8 cm3; (15)Molar Volume: 108.8 cm3; (16)Polarizability: 13.4×10-24cm3; (17)Surface Tension: 47.8 dyne/cm; (18)Density: 1.085 g/cm3; (19)Flash Point: 93.9 °C; (20)Enthalpy of Vaporization: 46.87 kJ/mol; (21)Boiling Point: 232.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0602 mmHg at 25°C. 

Uses of 2-Pyridylacetonitrile: It can react with ethoxymethylene-malonic acid diethyl ester to produce 1-cyano-4-oxo-4H-quinolizin-3-carboxylic acid ethyl ester. This reaction will need reagent sodium ethoxide, and the solvent ethanol. The reaction time is 45 minutes with temperature of 25°C, and the yield is about 55%  

2-Pyridylacetonitrile can react with ethoxymethylene-malonic acid diethyl ester to produce 1-cyano-4-oxo-4H-quinolizin-3-carboxylic acid ethyl ester

You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCc1ncccc1
(2)InChI: InChI=1/C7H6N2/c8-5-4-7-3-1-2-6-9-7/h1-3,6H,4H2
(3)InChIKey: UKVQBONVSSLJBB-UHFFFAOYAP 

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