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IUPAC name
(R/S) 2-pyrrolidinemethanol
68832-13-3 (D-prolinol) YesY
23356-96-9 (L-prolinol) N
3D model (Jmol) (D-prolinol): Interactive image
(L-prolinol): Interactive image
ChemSpider 2006673 (D-prolinol) N
555468 (L-prolinol) N
ECHA InfoCard 100.157.355
PubChem 2724541 (D-prolinol)
640091 (L-prolinol)
Molar mass 101.15 g/mol
Appearance Liquid
Density 1.036 g/mL liquid
Boiling point 74 to 76 °C (165 to 169 °F; 347 to 349 K) at 2 mmHg
Main hazards Irritant
R-phrases 36/37/38
S-phrases 26-36
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).
N verify (what is YesYN ?)
Infobox references
This article is about a compound used in synthesis of certain stimulants and should not be confused with a stimulant in that class the brand name of which is propalin

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.


Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[1][2] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.


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 reaction and the Michael reaction. [3][4]

See also[edit]


  1. ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Reduction of α-Amino Acids: L-Valinol Organic Syntheses, Collected Volume 7, p.530 (1990).
  2. ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
  3. ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron. 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1. 
  4. ^ Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama (1984). "Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent". J. Chem. Soc., Perkin Trans. 1 (12): 2887–2895. doi:10.1039/P19840002887.