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246565

Sigma-Aldrich

2-Pyridylacetonitrile

99%

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Empirical Formula (Hill Notation):
C7H6N2
CAS Number:
2739-97-1
Molecular Weight:
118.14
Beilstein:
111215
EC Number:
220-364-6
MDL number:
MFCD00006346
UNSPSC Code:
12352100
PubChem Substance ID:
24854814
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.525 (lit.)

bp

76-77 °C/2 mmHg (lit.)

density

1.059 g/mL at 25 °C (lit.)

SMILES string

N#CCc1ccccn1

InChI

1S/C7H6N2/c8-5-4-7-3-1-2-6-9-7/h1-3,6H,4H2

InChI key

UKVQBONVSSLJBB-UHFFFAOYSA-N

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General description

2-Pyridylacetonitrile undergoes coupling with aromatic diazonium salts to yield arylhydrazones. It also undergoes condensation with active malonic esters to yield 1-cyano-3-substituted 2-hydroxyquinolizin-4-ones. Acylation reaction of 2-pyridylacetonitrile with hot acetic anhydride has been reported.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H310,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Acylation and other reactions of 2-and 4-pyridylacetonitrile.
Gutsche CD and Voges HD.
The Journal of Organic Chemistry, 32(9), 2685-2689 (1969)
Mariam Abdullah Al-Sheikh et al.
Molecules (Basel, Switzerland), 14(11), 4406-4413 (2009-11-20)
2-Pyridylacetonitrile (1) couples with aromatic diazonium salts to yield arylhydrazones 2a-c, that were shown to exist in the syn-form 2 rather than the anti-form 4. Compounds 2a,c reacted with hydroxylamine in refluxing DMF to yield the interesting 1,2,3-triazolylpyridines 6. Attempts
F S Soliman et al.
Die Pharmazie, 32(5), 278-279 (1977-05-01)
Active malonic esters condense with 2-pyridylacetonitrile giving 1-cyano-3-substituted 2-hydroxyquinolizin-4-ones. Catalytic hydrogenation of the resulting products led to the corresponding 1-cyano-3-substituted-2-hydroxy-6.7.8.9-tetrahydroquinolizin-4-ones. On the other hand, condensation of the active malonic esters with beta-aminocrotononitrile afforded 5-cyano-3-substituted-4-hydroxy-6-methylpyridine-2-ones. The IR and NMR data are
Amit N Pandya et al.
Tetrahedron letters, 55(50), 6922-6924 (2014-12-17)
An efficient strategy for the synthesis of indolizines from readily available starting materials via oxidative C-H functionalization and
Masazumi Tamura et al.
Nature communications, 6, 8580-8580 (2015-10-06)
Multidentate materials formed by simply mixing heterogeneous and homogeneous components are promising for construction of versatile active sites on the surface of heterogeneous compounds, however, to the best of our knowledge, there are no reports on such materials. Self-assembly of

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