methyl (3R)-3-hydroxybutanoate

• ChemBase ID: 70371
• Molecular Formular: C5H10O3
• Molecular Mass: 118.1311
• Monoisotopic Mass: 118.06299418
• SMILES: C(=O)(C[C@@H](C)O)OC
• Canonical SMILES: COC(=O)C[C@H](O)C
• InChI: InChI=1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1
• InChIKey: LDLDJEAVRNAEBW-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3R)-3-hydroxybutanoate
• IUPAC Traditional name: methyl (3R)-3-hydroxybutanoate; methyl-(R)-3-hydroxybutyrate
• Synonyms: (R)-(-)-3-Hydroxybutyric acid methyl ester; Methyl (R)-(-)-3-hydroxybutyrate; (R)-Methyl 3-hydroxybutanoate; Methyl (R)-3-hydroxybutyrate; Methyl 3-(R)-hydroxybutyrate; Methyl (R)-3-hydroxybutanoate; (R)-(-)-3-羟丁酸甲酯; (R)-3-羟基丁酸甲酯

Database IDs

• CAS Number: 3976-69-0
• EC Number: 223-610-0
• MDL Number: MFCD00063289
• Beilstein Number: 3648161
• PubChem SID: 162036091; 24874704; 24854601
• PubChem CID: 2724279

CALCULATED PROPERTIES

• Acid pKa: 15.407248
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.24111195
• LogD (pH = 7.4): -0.24111195
• Log P: -0.24111195
• Molar Refractivity: 28.2332 cm^3
• Polarizability: 11.390625 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 56-58 °C/11 mmHg(lit.); 56-58°C/11mm; 56-58°C/11mm
• Flash Point: 163.4 °F; 73 °C; 73°C; 73°C(163°F)
• Density: 1.055; 1.055 g/mL at 20 °C(lit.)
• Refractive Index: 1.4220; n20/D 1.421(lit.); n20/D 1.422
• Optical Rotation: [α]20/D -19.5°, neat; [α]20/D -50±2°, c = 1.3% in chloroform stab. with amylenes; -48.5 (c=1.3 in chloroform)

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 38-41
• Safety Statements: 26-36/37; 26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H318-H315-H227
• GHS Precautionary statements: P210-P280B-P305+P351+P338-P310; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95+%; 97%; 98%; 99%
• Grade: puriss.
• Optical Purity: ee: 98% (GLC); enantiomeric ratio: ≥98:2 (GC)
• Linear Formula: CH3CH(OH)CH2CO2CH3

DETAILS

Sigma Aldrich - 243159

Application
Optically active starting material
Packaging
1 g in glass bottle

Sigma Aldrich - 54957

Other Notes
Important optically active compound for the preparation of various bifunctional building blocks 1,2,3,4

REFERENCES

• For use in the synthesis of chiral ?-lactams, see: J. Chem. Soc., Chem. Commun., 1376 (1988).
• Can undergo aldol-type reactions with aldehydes with either syn- or anti-selectivity according to the conditions: Chem. Lett., 1931 (1990).