Valinol

Valinol
Names
Preferred IUPAC name
(2S)-2-Amino-3-methylbutan-1-ol
Other names
(S)-(+)-2-Amino-3-methyl-1-butanol
Identifiers
CAS Number
  • 16369-05-4 (DL)
  • 2026-48-4 (L)
  • 4276-09-9 (D)
3D model (JSmol)
  • (DL): Interactive image
  • (L): Interactive image
  • (D): Interactive image
ChemSpider
  • 71352 (DL)
  • 556322 (L)
  • 5323522 (D)
ECHA InfoCard 100.036.734 Edit this at Wikidata
PubChem CID
  • 79019 (DL)
  • 640993 (L)
  • 6950587 (D)
InChI
  • (DL): InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3
    Key: NWYYWIJOWOLJNR-UHFFFAOYSA-N
  • (L): InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m1/s1
    Key: NWYYWIJOWOLJNR-RXMQYKEDSA-N
  • (D): InChI=1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m0/s1
    Key: NWYYWIJOWOLJNR-YFKPBYRVSA-N
  • (DL): CC(C)C(CO)N
  • (L): CC(C)[C@@H](CO)N
  • (D): CC(C)[C@H](CO)N
Properties
Chemical formula
 C5H13NO
Molar mass 103.165 g·mol−1
Appearance White to yellow crystalline powder
Density 0.926 g/mL
Melting point 30 to 34 °C (86 to 93 °F; 303 to 307 K)
Boiling point 189 to 190 °C (372 to 374 °F; 462 to 463 K)
Solubility in water
 Very soluble
Hazards
GHS labelling:[1]
Pictograms
 GHS07: Exclamation mark
Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P305+P351+P338
Flash point 90°C[1] closed cup
Safety data sheet (SDS) Sigma Aldrich[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Valinol is an organic compound named after, and commonly produced from, the amino acid valine. The compound is chiral and is produced almost exclusively as the S‑isomer (also designated as the L‑isomer), due to the abundant supply of S-valine. It is part of a broader class of amino alcohols.

Synthesis

Valinol can be generated by converting the carboxylic group of valine to an alcohol with a strong reducing agent such as lithium aluminium hydride,[2] or with NaBH4 and I2 (forming the borane–tetrahydrofuran complex).[3] In both cases the valinol produced can be subsequently purified by short path distillation.

Reactions

Valinol is mainly used to prepare chiral oxazolines, a process which can be achieved via a variety of methods. These oxazolines are principally used as ligands in asymmetric catalysis.[4]

See also

  • (S)-iPr-PHOX - an oxazoline ligand made using valinol

References

  1. ^ a b c Sigma-Aldrich Co., 2-Amino-3-methyl-1-butanol. Retrieved on 2014-10-22.
  2. ^ Dickman, D.A.; Meyers, A.I.; Smith, G.A.; Gawley, R.E. (1990). "Reduction of α-Amino Acids". Organic Syntheses. 7: 530. doi:10.15227/orgsyn.063.0136. Retrieved 11 October 2012.
  3. ^ McKennon, Marc J.; Meyers, A. I.; Drauz, Karlheinz; Schwarm, Michael (1993). "A convenient reduction of amino acids and their derivatives". The Journal of Organic Chemistry. 58 (13): 3568–3571. doi:10.1021/jo00065a020.
  4. ^ McManus, Helen A.; Guiry, Patrick J. (Sep 2004). "Recent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis". Chemical Reviews. 104 (9): 4151–4202. doi:10.1021/cr040642v. PMID 15352789.