methyl (2R)-2-hydroxy-2-phenylacetate

• ChemBase ID: 69754
• 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-/m1/s1
• InChIKey: ITATYELQCJRCCK-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R)-2-hydroxy-2-phenylacetate
• IUPAC Traditional name: methyl (2R)-2-hydroxy-2-phenylacetate
• Synonyms: (R)-(-)-alpha-Hydroxyphenylacetic acid methyl ester; (R)-(-)-Mandelic acid methyl ester; (-)-Methyl (R)-α-hydroxyphenylacetate; (-)-Methyl D-mandelate; Methyl (R)-(-)-mandelate; Methyl (R)-(-)-mandelate; (-)-Methyl D-mandelate; (-)-甲基(R)-α-羟基苯乙酸酯; D-(-)-扁桃酸甲酯; (R)-(-)-扁桃酸甲酯; (R)-(-)-扁桃酸甲酯; D-(-)-扁桃酸甲酯

Database IDs

• CAS Number: 20698-91-3
• MDL Number: MFCD00064247
• Beilstein Number: 3589447; 2937343
• PubChem SID: 162035479; 24855139
• PubChem CID: 2724623

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

• Melting Point: 56-58 °C; 56-58 °C(lit.); 56-58°C
• Flash Point: >110°C(230°F)
• Optical Rotation: [α]20/D -144.0°, c = 1 in methanol; [α]20/D -144±3°, c = 1% in methanol; -144 (c=1 in methanol)

Safety Information

• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, GC); 95+%; 98%; 99%
• Grade: purum
• Optical Purity: ee: 97% (HPLC)
• Linear Formula: C6H5CH(OH)CO2CH3
• Empirical Formula (Hill Notation): C9H10O3

DETAILS

Sigma Aldrich - 251550

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

Sigma Aldrich - 63456

Other Notes
This ester and derivatives are used as chiral building blocks and as auxiliaries1; Chiral derivatizing agent for acids in NMR2,3,4

REFERENCES

• Chiral derivatizing agent; see following entry.