methyl (2S)-2-hydroxy-2-phenylacetate

• ChemBase ID: 69777
• Molecular Formular: C9H10O3
• Molecular Mass: 166.1739
• Monoisotopic Mass: 166.06299418
• SMILES: C(=O)([C@@H](O)c1ccccc1)OC
• Canonical SMILES: COC(=O)[C@H](c1ccccc1)O
• InChI: InChI=1S/C9H10O3/c1-12-9(11)8(10)7-5-3-2-4-6-7/h2-6,8,10H,1H3/t8-/m0/s1
• InChIKey: ITATYELQCJRCCK-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-2-hydroxy-2-phenylacetate
• IUPAC Traditional name: methyl (2S)-2-hydroxy-2-phenylacetate
• Synonyms: (S)-(+)-Methyl Mandelate; (S)-Mandelic Acid Methyl Ester; (S)-Methyl Mandelate; L-(+)-Mandelic Acid Methyl Ester; Methyl (S)-2-Hydroxy-2-phenylacetate; Methyl (S)-α-H; Methyl d-Mandelate; +)-Mandelic Acid Methyl Ester; (+)-Methyl Mandelate; (S)-(+)-Mandelic Acid Methyl Ester; (+)-Methyl (S)-α-hydroxyphenylacetate; (+)-Methyl L-mandelate; Methyl (S)-(+)-mandelate; Methyl (S)-(+)-mandelate; (S)-(+)-alpha-Hydroxyphenylacetic acid methyl ester; (+)-甲基(S)-α-羟基苯乙酸酯; L-(+)-扁桃酸甲酯; (S)-(+)-扁桃酸甲酯; (S)-(-)-扁桃酸甲酯

Database IDs

• CAS Number: 21210-43-5
• MDL Number: MFCD00064246
• Beilstein Number: 2614741
• PubChem SID: 24855138; 162035502
• PubChem CID: 643570

CALCULATED PROPERTIES

• Acid pKa: 11.99351
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0417296
• LogD (pH = 7.4): 1.0417186
• Log P: 1.0417297
• Molar Refractivity: 43.4729 cm^3
• Polarizability: 17.2403 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 56-58 °C(lit.); 56-58°C
• Flash Point: >110°C(230°F)
• Optical Rotation: [α]20/D +144°, c = 1 in methanol; +144 (c= 1 in methanol)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false; 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; 95+%; 98%; 99%
• Optical Purity: ee: 98% (HPLC)
• Linear Formula: C6H5CH(OH)CO2CH3

DETAILS

Sigma Aldrich - 251542

General description
Optically active building block.
Packaging
5 g in glass bottle

REFERENCES

• Chiral derivatizing agent for determination of enantiomeric excess of alcohols and amines by NMR: Tetrahedron Lett., 2183 (1977); J. Chem. Soc., Perkin 2, 83 (1983).