Prolinol

Source: Wikipedia, the free encyclopedia.
Prolinol
Names
IUPAC name
(R/S) 2-pyrrolidinemethanol
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.157.355 Edit this at Wikidata
EC Number
  • 245-605-2
UNII
  • (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
  • (D-prolinol): C1C[C@@H](NC1)CO
  • (L-prolinol): C1C[C@H](NC1)CO
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
 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).
☒N verify (what is checkY☒N ?)

Prolinol is a chiral

enantiomers
: the D and L forms.

Preparation

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

Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or

Michael reaction
. [4][5]

See also

References

  1. ^ "D-Prolinol". pubchem.ncbi.nlm.nih.gov. Retrieved 27 December 2021.
  2. ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. "Reduction of α-Amino Acids: L-Valinol". Organic Syntheses; Collected Volumes, vol. 7, p. 530.
  3. ^ Enders, D.; Fey, P.; Kipphardt, H. "(S)-(–)-1-Amino-2-Methoxymethylpyrrolidine (SAMP) and (R)-(+)-1-Amino-2-Methoxymethylpyrrolidine (RAMP), Versatile Chiral Auxiliaries". Organic Syntheses; Collected Volumes, vol. 8, p. 26.
  4. doi:10.1016/S0040-4020(02)00516-1
    .
  5. doi:10.1039/P19840002887
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Prolinol&oldid=1075985403"