Valinol

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.

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
PubChem CID	79019 (DL) 640993 (L) 6950587 (D)
CompTox Dashboard (EPA)	DTXSID70862814
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
SMILES (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
Signal word	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

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. 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.