M2780

(1R,2S,5R)-(−)-Menthol

ReagentPlus^®, 99%

• Synonym(s): (−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol
• Empirical Formula (Hill Notation): C₁₀H₂₀O
• CAS Number: 2216-51-5
• Molecular Weight: 156.27
• Beilstein/REAXYS Number: 1902293
• EC Number: 218-690-9
• MDL number: MFCD00062979
• UNSPSC Code: 12352001
• PubChem Substance ID: 24896767
• NACRES: NA.22

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• vapor pressure: 0.8 mmHg ( 20 °C)
• product line: ReagentPlus^®
• assay: 99%
• optical activity: [α]20/D −50°, c = 10 in 95% ethanol
• optical purity: ee: 99% (GLC)
• bp: 212 °C (lit.)
• mp: 41-45 °C (lit.)
• solubility: water: 20 mg/mL, clear, colorless
• density: 0.89 g/mL at 25 °C (lit.)
• SMILES string: CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O
• InChI: 1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
• InChI key: NOOLISFMXDJSKH-KXUCPTDWSA-N

Description

General description

(1R,2S,5R)-(-)-Menthol is a monoterpene.

Application

(1R,2S,5R)-(-)-Menthol may be used to synthesize:

• chiral enantiopure 2-(1-hydroxyalkyl)pyridines, which can react with to form C3-symmetric tripodal ligands
• menthylphosphorodichioridite, a chiral derivatizing agent for the determination of enantiomeric purity of chiral diols or diamines by ³¹P NMR spectroscopy
• (2R,4S)-2,3,4,5-tetrahydro-2-(-)-menthyloxy-2-methyl-4-phenylpyrano-[3,2-c]-benzopyran-5-one, an intermediate to prepare a warfarin analog

It may also be used as a chiral auxiliary, to induce chirality while synthesizing (-)-horsfiline.

Used to prepare reagents for chiral vinylogous Darzens and Reformatsky reactions. Important chiral auxiliary employed in the resolution of acids and for stereocontrolled synthesis.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319
• pcodes: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: 201.2 °F - closed cup
• flash_point_c: 94 °C - closed cup