Prolinol

Names

IUPAC name

(R/S) 2-pyrrolidinemethanol

Identifiers

CAS Number

68832-13-3 (D-prolinol)^Y
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)

InChI

(D-prolinol): InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m1/s1

Key: HVVNJUAVDAZWCB-RXMQYKEDSA-N
(L-prolinol): InChI=1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m0/s1

Key: HVVNJUAVDAZWCB-YFKPBYRVSA-N

SMILES

(D-prolinol): C1C[C@@H](NC1)CO
(L-prolinol): C1C[C@H](NC1)CO

Properties

Chemical formula

C₅H₁₁NO

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

Hazards

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).

(what is ^YN ?)

Infobox references

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. 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.

...
Wikipedia