{{Chembox |ImageFile = S-valinol.svg |PIN = (2''S'')-2-Amino-3-methylbutan-1-ol |OtherNames = (''S'')-(+)-2-Amino-3-methyl-1-butanol |Section1={{Chembox Identifiers |CASNo = 16369-05-4 |CASNo_Comment = (<small>DL</small>) |CASNo1 = 2026-48-4 |CASNo1_Comment = (<small>L</small>) |CASNo2 = 4276-09-9 |CASNo2_Comment = (<small>D</small>) |PubChem = 79019 |PubChem_Comment = (<small>DL</small>) |PubChem1 = 640993 |PubChem1_Comment = (<small>L</small>) |PubChem2 = 6950587 |PubChem2_Comment = (<small>D</small>) |ChemSpiderID = 71352 |ChemSpiderID_Comment = (<small>DL</small>) |ChemSpiderID1 = 556322 |ChemSpiderID1_Comment = (<small>L</small>) |ChemSpiderID2 = 5323522 |ChemSpiderID2_Comment = (<small>D</small>) |SMILES = CC(C)C(CO)N |SMILES_Comment = (<small>DL</small>) |SMILES1 = CC(C)[C@@H](CO)N |SMILES1_Comment = (<small>L</small>) |SMILES2 = CC(C)[C@H](CO)N |SMILES2_Comment = (<small>D</small>) |InChI = 1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3 |InChIKey = NWYYWIJOWOLJNR-UHFFFAOYSA-N |InChI_Comment = (<small>DL</small>) |InChI1 = 1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m1/s1 |InChIKey1 = NWYYWIJOWOLJNR-RXMQYKEDSA-N |InChI1_Comment = (<small>L</small>) |InChI2 = 1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3/t5-/m0/s1 |InChIKey2 = NWYYWIJOWOLJNR-YFKPBYRVSA-N |InChI2_Comment = (<small>D</small>) }} |Section2={{Chembox Properties |C=5 | H=13 | N=1 | O=1 |Appearance = White to yellow crystalline powder |Density = 0.926 g/mL |MeltingPtC = 30 to 34 |BoilingPtC = 189 to 190 |Solubility = Very soluble }} |Section3={{Chembox Hazards |ExternalSDS = Sigma Aldrich<ref name="sigma">{{Sigma-Aldrich| id=184837 |name=2-Amino-3-methyl-1-butanol|accessdate=2014-10-22}}</ref> |GHSSignalWord = Warning |GHSPictograms = {{GHS07}} |HPhrases = {{H-phrases|315|319|335|}} |PPhrases = {{P-phrases|261|305+351+338}} |GHS_ref = <ref name="sigma" /> |FlashPt = 90°C |FlashPt_ref = <ref name="sigma" /> |FlashPt_notes = closed cup }} }}
'''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,<ref>{{cite journal|last=Dickman|first=D.A.|author2=Meyers, A.I. |author3=Smith, G.A. |author4=Gawley, R.E. |title=Reduction of α-Amino Acids|journal=Organic Syntheses|year=1990|volume=7|pages=530|url=http://www.orgsyn.org/orgsyn/prep.asp?prep=cv7p0530|accessdate=11 October 2012|doi=10.15227/orgsyn.063.0136|url-access=subscription}}</ref> or with NaBH<sub>4</sub> and I<sub>2</sub> (forming the borane–tetrahydrofuran complex).<ref>{{cite journal|last=McKennon|first=Marc J.|author2=Meyers, A. I. |author3=Drauz, Karlheinz |author4= Schwarm, Michael |title=A convenient reduction of amino acids and their derivatives|journal=The Journal of Organic Chemistry|year=1993|volume=58|issue=13|pages=3568–3571|doi=10.1021/jo00065a020}}</ref> 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.<ref>{{cite journal|last=McManus|first=Helen A.|author2=Guiry, Patrick J. |title=Recent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis|journal=Chemical Reviews|volume=104|issue=9|pages=4151–4202|doi=10.1021/cr040642v|pmid=15352789|date=Sep 2004}}</ref>
==See also== * (S)-iPr-PHOX - an oxazoline ligand made using valinol
== References == <references />
Category:Ligands Category:Primary alcohols Category:Amino alcohols