| Identification | Back Directory | [Name]
Methyl 2-(hydroxymethyl)acrylate | [CAS]
15484-46-5 | [Synonyms]
Methyl 2-(hydroxymethyl)
Methyl 2-(hydroxymethyl)acrylate
2-Hydroxymethyl-acrylic acid methyl ester
2-Propenoic acid, 2-(hydroxyMethyl)-, Methyl ester
Methyl 2-(hydroxyMethyl)acrylate, stabilized with 0.1 wt.% MEHQ
Methyl 2-(hydroxyMethyl)acrylate, 93%, stabilized with 0.1 wt.% MEHQ | [Molecular Formula]
C5H8O3 | [MDL Number]
MFCD12545894 | [MOL File]
15484-46-5.mol | [Molecular Weight]
116.12 |
| Chemical Properties | Back Directory | [Boiling point ]
63-65 °C(Press: 2.3 Torr) | [density ]
1.129 g/mL at 25 °C | [refractive index ]
n20/D1.456 | [Fp ]
90℃ | [storage temp. ]
2-8°C | [form ]
liquid | [pka]
13.66±0.10(Predicted) | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C5H8O3/c1-4(3-6)5(7)8-2/h6H,1,3H2,2H3 | [InChIKey]
RFUCOAQWQVDBEU-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C(CO)=C |
| Hazard Information | Back Directory | [Synthesis]
Example 106: Synthesis of methyl 2-(hydroxymethyl)acrylate
Trimethylphosphonoacetate (5.46 g, 30 mmol, 1.0 eq.) was dissolved in an appropriate amount of solvent at room temperature with rapid stirring. Subsequently, saturated K2CO3 aqueous solution (10 mL, 3.5 g, 117 mmol, 1.6 equiv) was added slowly. Next, paraformaldehyde (6.63 g, 48 mmol, 4.0 eq.) was added. After the addition was completed, the reaction mixture continued to be stirred for 2 hours. After completion of the reaction, the mixture was extracted with dichloromethane (DCM). The organic layers were combined and concentrated to give the target product methyl 2-(hydroxymethyl)acrylate (1.5 g, 44% yield) as a yellow oil. The product was characterized by 1H NMR (400 MHz, CD3OD) with the following chemical shifts: δ 6.29 (s, 1H), 5.83 (s, 1H), 3.75 (s, 3H), 3.72 (s, 2H). | [References]
[1] Angewandte Chemie - International Edition, 2015, vol. 54, # 6, p. 1929 - 1932
[2] Angew. Chem., 2015, vol. 127, # 6, p. 1949 - 1952,4
[3] Tetrahedron, 2008, vol. 64, # 17, p. 3701 - 3712
[4] Patent: WO2011/17561, 2011, A1. Location in patent: Page/Page column 72
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 18, p. 3539 - 3545 |
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