| Identification | More | [Name]
3-PYRIDYLACETONITRILE | [CAS]
6443-85-2 | [Synonyms]
3-(CYANOMETHYL)PYRIDINE
3-PYRIDINEACETONITRILE
3-PYRIDYLACETONITRILE
3-PYRIDYLMETHYL CYANIDE
PYRIDINE-3-ACETONITRILE
3-Pyridinylacetonitrile
Pyridine-3-acetonitrile,98%
NSC 83226 | [EINECS(EC#)]
229-241-1 | [Molecular Formula]
C7H6N2 | [MDL Number]
MFCD00006406 | [Molecular Weight]
118.14 | [MOL File]
6443-85-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
99-100 °C | [Boiling point ]
101-109 °C/1.5 mmHg (lit.) | [density ]
1.108 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.529(lit.)
| [Fp ]
209 °F
| [storage temp. ]
2-8°C
| [form ]
Liquid | [pka]
4.17±0.10(Predicted) | [color ]
very deep yellow
| [Water Solubility ]
Soluble in alcohol, ether, ketone. Insoluble in water. | [BRN ]
111292 | [InChI]
InChI=1S/C7H6N2/c8-4-3-7-2-1-5-9-6-7/h1-2,5-6H,3H2 | [InChIKey]
OIPHWUPMXHQWLR-UHFFFAOYSA-N | [SMILES]
C1=NC=CC=C1CC#N | [CAS DataBase Reference]
6443-85-2(CAS DataBase Reference) | [EPA Substance Registry System]
3-Pyridineacetonitrile (6443-85-2) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
3276 | [WGK Germany ]
3
| [F ]
10 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 |
| Hazard Information | Back Directory | [Uses]
3-Pyridineacetonitrile is a reactant used in the preparation of 1,7-naphthyridine derivatives as phosphodiesterase-4 inhibitors. | [Synthesis]
The general procedure for synthesizing 3-pyridylacetonitrile from pyridine-3-acetamide is as follows: general method: after completing the preparation of the amide intermediate, the operation of Example A is carried out. Decide the state of the reaction vessel according to the relationship between the boiling point of the amide intermediate at atmospheric pressure and the reaction temperature TB: if the boiling point of the amide intermediate is equal to or lower than TB, close the reaction vessel; if higher than TB, keep the reaction vessel open. Start the stirrer, set the speed to 600 rpm, adjust the reaction temperature to TB and maintain this temperature for TD hours until the reaction is essentially complete. Subsequently, the reaction vessel was sealed and connected to a vacuum pump, the system vacuum was adjusted to 20-50 mbar (depending on the nature of the nitrile product), and the distillate was collected as the target nitrile product. The yield of the product was calculated and samples were taken for NMR and elemental analysis to characterize the structure and purity of the resulting nitrile product. The specific reaction conditions and characterization results are detailed in Tables A-7 to A-12 below. the characterization data confirmed that the resulting nitrile products were of very high purity (>99%). In this series of examples for the preparation of the nitrile product, it is recommended to add 10 g of phosphorus pentoxide as a catalyst at once at the beginning of the reaction. | [References]
[1] Patent: CN104557610, 2018, B. Location in patent: Paragraph 0153; 0154; 0155; 0158; 0159
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 1988
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 5752,5756 |
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