4-oxo-4-phenylbutanoic acid

• ChemBase ID: 91120
• Molecular Formular: C10H10O3
• Molecular Mass: 178.1846
• Monoisotopic Mass: 178.06299418
• SMILES: O=C(CCC(=O)c1ccccc1)O
• Canonical SMILES: O=C(c1ccccc1)CCC(=O)O
• InChI: InChI=1S/C10H10O3/c11-9(6-7-10(12)13)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,12,13)
• InChIKey: KMQLIDDEQAJAGJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-oxo-4-phenylbutanoic acid
• IUPAC Traditional name: 4-oxo-4-phenylbutanoic acid
• Synonyms: β-BENZOYLPROPIONIC ACID; 3-Benzoylpropionic acid; 4-Oxo-4-phenylbutyric acid; 3-Benzoylpropionic acid; 4-Oxo-4-phenylbutanoic acid; 4-Oxo-4-phenyl-butanoic Acid; 4-Oxo-4-phenyl-butyric Acid; 4-Phenyl-4-oxobutanoic Acid; 3-benzoyl-propanoic Acid; β-Benzoyl-propionic Αcid; γ-Oxobenzene-butanoic Acid; 3-Benzoylpropanoic Acid; 4-羰基-4-苯基丁酸; 3-苯甲酰丙酸

Database IDs

• CAS Number: 2051-95-8
• EC Number: 218-135-0
• MDL Number: MFCD00002792
• Beilstein Number: 639757
• PubChem SID: 24891586; 24847967; 162077824
• PubChem CID: 72871

CALCULATED PROPERTIES

• Acid pKa: 4.1085
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.049877256
• LogD (pH = 7.4): -1.7378205
• Log P: 1.355756
• Molar Refractivity: 47.3541 cm^3
• Polarizability: 18.27144 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Pale Orange Solid
• Melting Point: 114-117 °C; 114-117 °C(lit.); 114-120°C; 116-118°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (T); 98+%; 99%
• Grade: purum
• Linear Formula: C6H5COCH2CH2COOH

DETAILS

MP Biomedicals - 05203400

MP Biomedicals Rare Chemical collection

Sigma Aldrich - B13802

Packaging
25, 100 g in poly bottle

Sigma Aldrich - 13055

Other Notes
Protecting group reagent for hydroxyl functions in nucleosides1

REFERENCES

• Can be used to protect alcohols as keto esters. Hydrazine reacts first with the ketone carbonyl and cleaves the ester intramolecularly by a "trigger" mechanism: J. Am. Chem. Soc., 91, 3356 (1969).
• Enantioselective ɑ-mono- or dialkylation can be effected using L-(+)-Valinol, L11300, as a chiral auxiliary: J. Am. Chem. Soc., 106, 1146 (1984).