2-(methoxycarbonyl)benzoic acid

• ChemBase ID: 150220
• Molecular Formular: C9H8O4
• Molecular Mass: 180.15742
• Monoisotopic Mass: 180.04225874
• SMILES: COC(=O)c1ccccc1C(=O)O
• Canonical SMILES: COC(=O)c1ccccc1C(=O)O
• InChI: InChI=1S/C9H8O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-5H,1H3,(H,10,11)
• InChIKey: FNJSWIPFHMKRAT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(methoxycarbonyl)benzoic acid
• IUPAC Traditional name: methyl hydrogen phthalate
• Synonyms: 2-(Methoxycarbonyl)benzoic acid; Monomethyl phthalate; mono-Methyl phthalate; 1,2-Benzenedicarboxylic Acid 1-Methyl Ester; Phthalic Acid Methyl Ester; Phthalic Acid Monomethyl Ester; 2-(1-Methoxycarbonyl)benzoic Acid; Methyl 2-Carboxybenzoate; Methyl Hydrogen Phthalate; Methyl Phthalate; MMP; NSC 8281; Monomethyl Phthalate; Benzene-1,2-dicarboxylic acid monomethyl ester; Methyl hydrogen phthalate; 单甲基邻苯二甲酸酯; 邻苯二甲酸单甲酯; 邻苯二甲酸氢甲酯

Database IDs

• CAS Number: 4376-18-5
• EC Number: 224-476-6
• MDL Number: MFCD00002466
• Beilstein Number: 2048766
• PubChem SID: 24859094; 162244381; 24862811
• PubChem CID: 20392

CALCULATED PROPERTIES

• Acid pKa: 3.0856395
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.74962264
• LogD (pH = 7.4): -1.8291929
• Log P: 1.6343057
• Molar Refractivity: 45.3395 cm^3
• Polarizability: 17.141464 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 76-78°C; 81-84°C; 82-84 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• 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: 97%; 98%
• Grade: analytical standard, for environmental analysis
• Linear Formula: 2-(HO2C)C6H4CO2CH3

DETAILS

Sigma Aldrich - 317640

Packaging
25, 100 g in glass bottle

Toronto Research Chemicals - M566540

Phthalate Ester metabolite, linked to precocious puberty.

REFERENCES

• Engel, S., et al.: NeuroToxicol., 30, 522 (2009)
• Blair, J., et al.: Environ., Sci., Technol., 43, 6262 (2009)
• Xu, Z., et al.: Environ. Sci. Technol., 44, 3130 (2009)
• Clewell, R., et al.: Toxicol. in Vitro, 24, 327 (2009)
• Undergoes a modified Curtius rearrangement via a mixed anhydride. The resulting isocyanate has been cyclized with, e.g. alanine to give chiral quinazoline-2,4-dione derivatives: Heterocycles, 36, 1305 (1993):