3-oxo-3-phenylpropanenitrile

• ChemBase ID: 9995
• Molecular Formular: C9H7NO
• Molecular Mass: 145.15798
• Monoisotopic Mass: 145.05276385
• SMILES: O=C(CC#N)c1ccccc1
• Canonical SMILES: N#CCC(=O)c1ccccc1
• InChI: InChI=1S/C9H7NO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5H,6H2
• InChIKey: ZJRCIQAMTAINCB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-oxo-3-phenylpropanenitrile
• IUPAC Traditional name: benzoylacetonitrile
• Synonyms: Benzoylacetonitrile; β-Oxohydrocinnamonitrile; Benzoylacetonitrile; Phenacyl Cyanide; α-Cyanoacetophenone; NSC 4713; 3-oxo-3-phenylpropanenitrile; 3-Oxo-3-phenylpropanenitrile; 3-Oxo-3-phenylpropionitrile; omega-Cyanoacetophenone; beta-Oxohydrocinnamonitrile; Benzoyl acetonitrile; 苯酰乙腈; 苯甲酰乙腈

Database IDs

• CAS Number: 614-16-4
• EC Number: 210-369-1
• MDL Number: MFCD00001942
• Beilstein Number: 386745
• PubChem SID: 24856193; 160973302
• PubChem CID: 64799

CALCULATED PROPERTIES

• Acid pKa: 13.053396
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4810706
• LogD (pH = 7.4): 1.4810697
• Log P: 1.4810706
• Molar Refractivity: 41.7842 cm^3
• Polarizability: 15.743013 Å^3
• Polar Surface Area: 40.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 79-83°C; 82 - 83°C; 82-83 °C(lit.); 82-83°C; 82-83°C
• Boiling Point: 159-160°C/10mm; 159-160°C/10mm; 160 °C/10 mmHg(lit.); 160°C 10mm
• Hydrophobicity(logP): 0.719

Safety Information

• Storage Warning: Harmful/Irritant/Light Sensitive; IRRITANT
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false; 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 98%; 98+%; 99%
• Linear Formula: C6H5COCH2CN

DETAILS

Sigma Aldrich - 272728

Packaging
5 g in glass bottle
Application
Building block for the preparation of 4H-pyrans,1,2,3 2-pyridones,4,5 furans,6 and carbocyclics.7,8,9

Toronto Research Chemicals - B207920

Used as a building block for the preparation of 4H-pyrans, 2-pyridones, furans and carbocyclics.

REFERENCES

• Herschhorn, A., et al.: J. Med. Chem., 50, 3402 (2007)
• Active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines: Synthesis, 775 (1989). Reaction with tosic anhydride, followed by diethyl aminomalonate provides a short, facile synthesis of 3-aminopyrrole-2-carboxylates: J. Org. Chem., 65, 2603 (2000):