(2E)-3-(4-chlorophenyl)-2-cyanoprop-2-enoic acid

• ChemBase ID: 41252
• Molecular Formular: C10H6ClNO2
• Molecular Mass: 207.61314
• Monoisotopic Mass: 207.00870612
• SMILES: c1c(ccc(c1)/C=C(/C(=O)O)\C#N)Cl
• Canonical SMILES: N#C/C(=C\c1ccc(cc1)Cl)/C(=O)O
• InChI: InChI=1S/C10H6ClNO2/c11-9-3-1-7(2-4-9)5-8(6-12)10(13)14/h1-5H,(H,13,14)/b8-5+
• InChIKey: MXCRRKYUQNHWLJ-VMPITWQZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(4-chlorophenyl)-2-cyanoprop-2-enoic acid
• IUPAC Traditional name: (2E)-3-(4-chlorophenyl)-2-cyanoprop-2-enoic acid
• Synonyms: (2E)-3-(4-Chlorophenyl)-2-cyano-2-propenoic Acid; (E)-2-Cyano-3-(naphthalen-2-yl)acrylic Acid; 3-(4-Chlorophenyl)-2-cyanoacrylic Acid; 4-Chloro-α-cyanocinnamic Acid; 3-(4-Chlorophenyl)-2-cyanoacrylic acid; 3-(4-Chloro-phenyl)-2-cyano-acrylic acid

Database IDs

• CAS Number: 20374-46-3
• MDL Number: MFCD02317172
• PubChem SID: 162046015
• PubChem CID: 2363776

CALCULATED PROPERTIES

• Acid pKa: 2.1396296
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.58391035
• LogD (pH = 7.4): -0.9694843
• Log P: 2.5519896
• Molar Refractivity: 52.9183 cm^3
• Polarizability: 19.787363 Å^3
• Polar Surface Area: 61.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 191 - 193 °C; 191-193°C; 201 - 203°C
• Hydrophobicity(logP): 2.275

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: > 95%; >95%; 95%

REFERENCES

• Jaskolla, T.W. et al.: Proc. Nat Acad. Sci. U.S.A., 105, 12200 (2008)
• Jaskolla, T.W. et al.: J. Proteome Res., 8, 3588 (2008)
• Towers, M.W. et al.: J. Proteome Res., 9, 1931 (2008)