Prolinol
(Redirected from L-Prolinol)
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| Names | |||
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| IUPAC name
(R/S) 2-pyrrolidinemethanol
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| Identifiers | |||
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3D model (JSmol)
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| ChemSpider | |||
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| EC Number |
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PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C5H11NO | |||
| Molar mass | 101.149 g·mol−1 | ||
| Appearance | Liquid | ||
| Density | 1.036 g/mL (liquid) | ||
| Boiling point | 74–76 °C (165–169 °F; 347–349 K) at 2 mmHg | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards
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Irritant | ||
| GHS labelling:[1] | |||
| GHS07: Exclamation mark | |||
| Warning | |||
| H315, H319, H335 | |||
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |||
| Flash point | 86 °C (187 °F; 359 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.
Preparation
[edit | edit source]Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[2][3] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
Use
[edit | edit source]Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos–Parrish–Eder–Sauer–Wiechert reaction, the Baylis–Hillman reaction, Noyori type reactions and the Michael reaction. [4][5]
See also
[edit | edit source]References
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