2-hydroxy-2-phenylacetic acid

• ChemBase ID: 70369
• Molecular Formular: C8H8O3
• Molecular Mass: 152.14732
• Monoisotopic Mass: 152.04734412
• SMILES: C(=O)(C(c1ccccc1)O)O
• Canonical SMILES: OC(c1ccccc1)C(=O)O
• InChI: InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)
• InChIKey: IWYDHOAUDWTVEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-phenylacetic acid
• IUPAC Traditional name: mandelic acid
• Synonyms: 2-Hydroxy-2-phenylacetic acid; α-Hydroxy-α-toluic acid; DL-MANDELIC ACID; DL-Mandelic acid; Mandelic acid; Phenylglycolic acid; Mandelic acid; Mandelic acid; (±)-α-Hydroxyphenylacetic acid; (+/-)-alpha-Hydroxyphenylacetic acid; (±)-Mandelic acid; (±)-α-羟基苯乙酸; DL-扁桃酸; 扁桃酸; (+/-)-扁桃酸

Database IDs

• CAS Number: 611-71-2,611-72-3,17199-29-0,90-64-2; 611-72-3; 90-64-2
• EC Number: 202-007-6
• MDL Number: MFCD00064250
• Beilstein Number: 510011
• Merck Index: 145717
• PubChem SID: 24896602; 162036089; 24882645
• PubChem CID: 1292
• CHEBI ID: 35825
• ATC CODE: J01XX06; B05CA06
• CHEMBL: 1609
• Chemspider ID: 1253
• Unique Ingredient Identifier: NH496X0UJX
• Wikipedia Title: Mandelic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.7512336
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.85347056
• LogD (pH = 7.4): -2.3882656
• Log P: 0.89583564
• Molar Refractivity: 38.7038 cm^3
• Polarizability: 15.161119 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 15.87 g per 100 mL in water
• Apperance: White crystalline powder
• Melting Point: 117-120 °C; 118-121°C; 119 °C (optically pure: 132 – 135 °C); 119-121 °C(lit.); 120-122°C
• Boiling Point: Decomposes
• Flash Point: 162.6°C (324.68°F)
• Density: 1.30 g/cm^3
• pKa: 3.41

Safety Information

• Storage Condition: Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT; Light Sensitive
• RTECS: OO6300000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305+P351+P338-P310
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); ≥99.0%; ≥99.0% (T); 95+%; 97%; 98%; 99%
• Grade: purum
• Ignition Residue: ≤0.05%
• Quality: for gravimetric determination of Zr
• Linear Formula: C6H5CH(OH)CO2H; C6H5CH(OH)COOH

DETAILS

MP Biomedicals - 05211168

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02102246

Crystalline
Purity: 98%

Sigma Aldrich - M2101

Packaging
250, 500 g in poly bottle

REFERENCES

• Forms a cyclic isopropylidene derivative with acetone, providing a means of O-protection. Subsequent reaction with ammonia gives the amide: Org. Synth. Coll., 3, 536 (1955).