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Myrcenol

Catalog Number

ACM543395-1

CAS

543-39-5

Structure

IUPAC Name

2-Methyl-6-methylideneoct-7-en-2-ol

Synonyms

7-Octen-2-ol, 2-methyl-6-methylene

Molecular Weight

154.25

Molecular Formula

C10H18O

Canonical SMILES

CC(C)(CCCC(=C)C=C)O

InChI

InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3

InChI Key

DUNCVNHORHNONW-UHFFFAOYSA-N

Boiling Point

217.64 °C

Flash Point

89 °C

Purity

95%+

Density

0.8389 g/mL at 25 °C(lit.)

Solubility

water, 260.9 mg/L @ 25 °C (est)

Appearance

Colorless to pale yellow clear liquid (est)

Active Content

95%

Physical State

Liquid

Typical Applications

Use as perfume.
Use as intermediate in organic synthesis.

MSDS

Download MSDS

COA

Download COA

Spec Sheet

Download Spec Sheet

Case Study

Myrcenol-based Monomer for Carbon Anionic Polymerization

Myrcenol-based Monomer for Carbon Anionic Polymerization Wahlen, Christian, et al. Macromolecules 53.20 (2020): 9008-9017.

The tremendous potential of terpenes in materials science is far from being exhausted, particularly in the field of carbon anionic polymerization. Research has shown that highly active carbanion chain ends can induce the elimination reaction of 2-alkoxy-1,3-butadienes, leading to an unexpected transformation of the monomer structure under polymerization conditions, the so-called "backbiting" phenomenon. This can be avoided by the introduction of the alkyl spacer present naturally in β-myrcene. Terpene compounds with polymerizable diene units are readily available compounds and potential candidates for bio-based monomers for carbon anionic polymerization. One potential candidate is β-myrcenol.
Preparation of (tert-Butyldimethylsilyloxy)-2-methyl-6-methyleneocta-2,7-diene (MyrOSi) Using β-Myrcenol
β-Myrcenol (7.6 g, 50 mmol) and imidazole (8.51 g, 125 mmol, 2.5 equiv) were dissolved in 15 mL of dichloromethane. A solution of tert-butyldimethylchlorosilane (7.2 g, 48 mmol, 0.95 equiv) in 15 mL of dichloromethane was added dropwise to the solution containing β-myrcenol, cooled to 0 °C. The solution was stirred for 24 hours under argon atmosphere. Afterwards, the solution was washed with 50 mL of a 5% NaHCO₃ aqueous solution. The organic layer was separated, and the aqueous layer was washed several times with n-hexane (3 × 20 mL). The combined organic layers were dried over MgSO₄. Solvent was removed under vacuum to give the crude product, which was purified by column chromatography (silica gel, toluene, Rf = 0.89) to yield 12.8 g (47.9 mmol) of pure MyrOSi (yield = 96%).

Custom Q&A

What is the product name of the chemical with CAS number 543-39-5?

The product name is Myrcenol.

What are the synonyms for Myrcenol?

The synonyms for Myrcenol are 7-Octen-2-ol and 2-methyl-6-methylene.

What is the IUPAC name for Myrcenol?

The IUPAC name for Myrcenol is 2-Methyl-6-methylideneoct-7-en-2-ol.

What is the molecular weight of Myrcenol?

The molecular weight of Myrcenol is 154.25.

What is the molecular formula of Myrcenol?

The molecular formula of Myrcenol is C10H18O.

What is the boiling point of Myrcenol?

The boiling point of Myrcenol is 217.64 °C.

What is the flash point of Myrcenol?

The flash point of Myrcenol is 89 °C.

What is the purity of Myrcenol?

The purity of Myrcenol is 95%+.

What is the density of Myrcenol at 25°C?

The density of Myrcenol at 25°C is 0.8389 g/mL.

What are the typical applications of Myrcenol?

The typical applications of Myrcenol are its use as a perfume and as an intermediate in organic synthesis.

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