methyl 4-(cyanomethyl)benzoate

• ChemBase ID: 142410
• Molecular Formular: C10H9NO2
• Molecular Mass: 175.18396
• Monoisotopic Mass: 175.06332853
• SMILES: COC(=O)c1ccc(cc1)CC#N
• Canonical SMILES: N#CCc1ccc(cc1)C(=O)OC
• InChI: InChI=1S/C10H9NO2/c1-13-10(12)9-4-2-8(3-5-9)6-7-11/h2-5H,6H2,1H3
• InChIKey: XRZGMNGGCZTNGE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-(cyanomethyl)benzoate
• IUPAC Traditional name: methyl 4-(cyanomethyl)benzoate
• Synonyms: Methyl 4-(cyanomethyl)benzoate; 4-(Cyanomethyl)benzoic Acid Methyl Ester; α-Cyano-p-toluic Acid Methyl Ester; 4-Cyanomethylbenzoic Acid Methyl Ester; Methyl 4-Cyanomethylbenzoate; Methyl p-(Cyanomethyl)benzoate; Methyl α-Cyano-p-toluate; [p-(Methoxycarbonyl)phenyl]acetonitrile; Methyl 4-(Cyanomethyl)benzoate; 对氰基甲基苯甲酸甲酯

Database IDs

• CAS Number: 76469-88-0
• MDL Number: MFCD00060695
• PubChem SID: 24884115; 162236640
• PubChem CID: 848548

CALCULATED PROPERTIES

• Acid pKa: 13.541701
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.6724199
• LogD (pH = 7.4): 1.6724197
• Log P: 1.6724199
• Molar Refractivity: 48.3702 cm^3
• Polarizability: 18.272562 Å^3
• Polar Surface Area: 50.09 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 55-58 °C(lit.); 60 - 62°C
• Boiling Point: 110 °C/0.2 mmHg(lit.)
• Hydrophobicity(logP): 1.533

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 96%; 98%
• Linear Formula: CH3OOCC6H4CH2CN

DETAILS

Sigma Aldrich - 655597

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - M294750

The key intermediate of Fexofenadine (F322490).

REFERENCES

• Slater, J., et al.: Drugs, 57, 31 (1999)
• Lv, B., et al.: Chin. J. Med. Chem., 14, 96 (1999)
• Mazier, C., et al.: Bioorg. Med. Chem. Lett., 14, 5423 (1999)