Key Documents

906263

cis-(+)-Limonene oxide

Name: <I>cis</I>-(+)-Limonene oxide
Brand: ALDRICH

Synonym(s):

(+)-cis-Limonene-1,2-epoxide, (1R,4R,6S)-1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane, cis-(+)-1,2-Epoxy-p-menth-8-ene

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₆O

CAS Number:

4680-24-4

Molecular Weight:

152.23

UNSPSC Code:

12352212

NACRES:

NA.22

MDL number:

MFCD09996820

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Properties

form

liquid

density

0.932 g/mL

functional group

ether

SMILES string

O1[C@@]2([C@H]1C[C@H](CC2)C(=C)C)C

InChI

1S/C10H16O/c1-7(2)8-4-5-10(3)9(6-8)11-10/h8-9H,1,4-6H2,2-3H3/t8-,9+,10-/m0/s1

InChI key

CCEFMUBVSUDRLG-AEJSXWLSSA-N

Description

Application

cis-(+)-Limonene oxide can be used as:

A monomer to prepare poly(limonene)carbonate by Al(III) catalyzed coupling reaction with CO₂.
A reactant to prepare trans-diaxial diol via diastereoselective ring-opening reaction using molybdenum complex catalyst.
A reactant to synthesize trans-dihydrocarvone via isomerization reaction in the presence of silica-supported tungstophosphoric acid as a catalyst and dialkylcarbonate as a green solvent.

cis-(+)-Limonene oxide is a valuable chiral terpene oxide building block.

Other Notes

Unlocking P(V): Reagents for chiral phosphorothioate synthesis

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

160.7 °F

flash_point_c

71.5 °C

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