Valinol

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title: "Valinol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["ligands", "primary-alcohols", "amino-alcohols"] topic_path: "general/ligands" source: "https://en.wikipedia.org/wiki/Valinol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|ImageFile = S-valinol.svg |PIN = (2S)-2-Amino-3-methylbutan-1-ol |OtherNames = (S)-(+)-2-Amino-3-methyl-1-butanol |Section1={{Chembox Identifiers |CASNo = 16369-05-4 |CASNo_Comment = (DL) |CASNo1 = 2026-48-4 |CASNo1_Comment = (L) |CASNo2 = 4276-09-9 |CASNo2_Comment = (D) |PubChem = 79019 |PubChem_Comment = (DL) |PubChem1 = 640993 |PubChem1_Comment = (L) |PubChem2 = 6950587 |PubChem2_Comment = (D) |ChemSpiderID = 71352 |ChemSpiderID_Comment = (DL) |ChemSpiderID1 = 556322 |ChemSpiderID1_Comment = (L) |ChemSpiderID2 = 5323522 |ChemSpiderID2_Comment = (D) |SMILES = CC(C)C(CO)N |SMILES_Comment = (DL) |SMILES1 = CC(C)C@@HN |SMILES1_Comment = (L) |SMILES2 = CC(C)C@HN |SMILES2_Comment = (D) |InChI = 1S/C5H13NO/c1-4(2)5(6)3-7/h4-5,7H,3,6H2,1-2H3 |InChIKey = NWYYWIJOWOLJNR-UHFFFAOYSA-N |InChI_Comment = (DL) |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 = (L) |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 = (D) |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 |GHSSignalWord = Warning |GHSPictograms = |HPhrases = |PPhrases = |GHS_ref = |FlashPt = 90°C |FlashPt_ref = |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, or with NaBH4 and I2 (forming the borane–tetrahydrofuran complex). 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.

References

References

  1. {{Sigma-Aldrich
  2. Dickman, D.A.. (1990). "Reduction of α-Amino Acids". Organic Syntheses.
  3. McKennon, Marc J.. (1993). "A convenient reduction of amino acids and their derivatives". The Journal of Organic Chemistry.
  4. McManus, Helen A.. (Sep 2004). "Recent Developments in the Application of Oxazoline-Containing Ligands in Asymmetric Catalysis". Chemical Reviews.

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ligandsprimary-alcoholsamino-alcohols