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M2780 Sigma-Aldrich

(1R,2S,5R)-(−)-Menthol

ReagentPlus®, 99%

Synonym: (−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol

  • CAS Number 2216-51-5

  • Empirical Formula (Hill Notation) C10H20O

  • Molecular Weight 156.27

  •  Beilstein/REAXYS Number 1902293

  •  EC Number 218-690-9

  •  MDL number MFCD00062979

  •  PubChem Substance ID 24896767

  •  NACRES NA.22

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Properties

Related Categories Alcohols, Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Organic Building Blocks More...
Quality Level   200
biological source   synthetic (organic)
grade   ReagentPlus®
vapor pressure   0.8 mmHg ( 20 °C)
assay   99%
optical activity   [α]20/D −50°, c = 10 in 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.

Packaging

25, 100, 500 g in poly bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
Flash Point(F) 
201.2 °F - closed cup
Flash Point(C) 
94 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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