M2780
(1R,2S,5R)-(−)-Menthol
ReagentPlus®, 99%
Synonym(s):
(−)-Menthol, (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol, 5-Methyl-2-(1-methylethyl)cyclohexanol
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About This Item
Empirical Formula (Hill Notation):
C10H20O
CAS Number:
Molecular Weight:
156.27
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-690-9
Beilstein/REAXYS Number:
1902293
MDL number:
Assay:
99%
Biological source:
synthetic (organic)
Solubility:
water: 20 mg/mL, clear, colorless
biological source
synthetic (organic)
Quality Level
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
General description
(1R,2S,5R)-(-)-Menthol is a monoterpene.
Application
Used to prepare reagents for chiral vinylogous Darzens and Reformatsky reactions. Important chiral auxiliary employed in the resolution of acids and for stereocontrolled synthesis.
(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
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
201.2 °F - closed cup
flash_point_c
94 °C - closed cup
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Fieser, M.
Reagents for Organic Synthesis, 16, 203-203 (1992)
Oxindole alkaloids. A novel non-biomimetic entry to (-)-Horsfiline.
Palmisano G, et al.
Tetrahedron Asymmetry, 7(1), 1-4 (1996)
An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition.
Cravotto G, et al.
Tetrahedron Asymmetry, 12(5), 707-709 (2001)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| M2780-10MG | 04061834046073 |
| M2780-500G-A | 04061834046097 |
| M2780-25G-A | 04061834046080 |
| M2780-100G-A | 04061834046066 |