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ChemicalBook--->CAS DataBase List--->18289-89-9

18289-89-9

18289-89-9 Structure

18289-89-9 Structure
IdentificationBack Directory
[Name]

(R)-Methyl 2,3-dihydroxypropanoate
[CAS]

18289-89-9
[Synonyms]

Methyl D-(-)-glycerate
Methyl (R)-2,3-Dihydroxypropionate
(R) Methyl-2,3-dihydroxypropionate
methyl (R)-2,3-dihydroxypropanoate
(R)-Methyl 2,3-dihydroxypropanoate
methyl (2R)-2,3-dihydroxypropanoate
Propanoic acid, 2,3-dihydroxy-, methyl ester, (2R)-
[Molecular Formula]

C4H8O4
[MDL Number]

MFCD06204263
[MOL File]

18289-89-9.mol
[Molecular Weight]

120.1
Chemical PropertiesBack Directory
[Boiling point ]

140 °C(Press: 15 Torr)
[density ]

1.2795 g/cm3
[storage temp. ]

2-8°C
[pka]

12.26±0.20(Predicted)
[Appearance]

Light yellow to yellow Liquid
[Optical Rotation]

12.5°(C=0.01g/ml CHCL3)
[InChI]

InChI=1S/C4H8O4/c1-8-4(7)3(6)2-5/h3,5-6H,2H2,1H3/t3-/m1/s1
[InChIKey]

COFCNNXZXGCREM-GSVOUGTGSA-N
[SMILES]

C(OC)(=O)[C@H](O)CO
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501
Spectrum DetailBack Directory
[Spectrum Detail]

(R)-Methyl 2,3-dihydroxypropanoate(18289-89-9)1HNMR
Hazard InformationBack Directory
[Synthesis]

(R)-(+)-2,2-DIMETHYL-1,3-DIOXOLANE-4-CARBOXYLIC ACID METHYL ESTER

52373-72-5

(R)-Methyl 2,3-dihydroxypropanoate

18289-89-9

General procedure for the synthesis of methyl (R)-2,3-dihydroxypropionate from methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate: 1. dissolve methyl (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (1 g, 6.24 mmol) in a mixed solvent of acetic acid (14 ml) and water (6 ml). 2. The reaction mixture was stirred at room temperature for 18 hours. 3. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. 4. The resulting residue was distilled three times azeotropically with toluene to completely remove water and residual acetic acid. 5. Methyl (R)-2,3-dihydroxypropionate (610.6 mg, 81% yield) was finally obtained. Product characterization data: 1H NMR (CDCl3, 400MHz) δ 4.29 (dd, 1H, J = 3.8, 3.3Hz), 3.91 (dd, 1H, J = 11.7, 3.3Hz), 3.85 (dd, 1H, J = 11.7, 3.8Hz), 3.84 (s, 3H).

[References]

[1] Journal of Medicinal Chemistry, 1992, vol. 35, # 17, p. 3223 - 3230
[2] Acta Chemica Scandinavica, 1998, vol. 52, # 6, p. 819 - 823
[3] Patent: US2006/270634, 2006, A1. Location in patent: Page/Page column 2; sheet 4
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 34, p. 9898 - 9902
[5] Angew. Chem., 2015, vol. 127, # 34, p. 10036 - 10040,5
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