3-Cyclohexene-1-methanol, also known as Cyclohexene Methanol, is an organic compound with the CAS number 1679-51-2. Its molecular formula is C7H12O, with a molecular weight of 112.17 g/mol. This compound belongs to the cycloalkene family and features a hydroxyl functional group (-OH) attached to a cyclohexene ring, making it a cyclic allylic alcohol.

The compound is also referred to by several synonyms including:

• 3-Cyclohexene-1-carbinol
• 4-(Hydroxymethyl)cyclohexene
• 1,2,3,6-Tetrahydrobenzyl alcohol
• 1-Hydroxymethyl-3-cyclohexene
• Cyclohex-3-en-1-ylmethanol

3-Cyclohexene-1-methanol appears as a clear, colorless liquid with moderate viscosity. The compound contains both an alkene functional group and a primary alcohol group, giving it unique chemical reactivity that makes it valuable in various synthetic applications.

Was sind die Vorteile?

Versatile Chemical Intermediate

3-Cyclohexene-1-methanol serves as a versatile chemical intermediate in organic synthesis. The presence of both the hydroxyl group and the carbon-carbon double bond allows for multiple chemical transformations, making it an excellent building block for more complex molecules.

Polymer Synthesis Applications

One of the significant benefits of this compound is its role in polymer chemistry. It has been successfully used in the synthesis of novel macromonomers of epoxy end-functionalized polystyrene via atom transfer radical polymerization (ATRP). This application demonstrates its importance in advanced materials science.

Photo-cross-linkable Polymers

The compound is particularly valuable in the preparation of photo-cross-linkable polymers with redissolution properties. This makes it useful in applications requiring precise control over polymer properties, such as in coatings, adhesives, and advanced manufacturing processes.

Potential Anti-cancer Properties

Research has shown that 3-Cyclohexene-1-methanol exhibits interesting biological activities:

• Reduce tumor size in mice by inhibiting cell proliferation through cationic polymerization with DNA
• Inhibit growth of MCF-7 breast cancer cells in vitro
• Induce cell death in cancer cells

These findings suggest potential therapeutic applications, though further research is needed.

Wozu dient es?

Industrielle Anwendungen

Polymer and Materials Science:

• Synthesis of epoxy end-functionalized polymers via ATRP
• Preparation of photo-cross-linkable polymers
• Development of specialty coatings and adhesives

Coatings Industry: Used as a component in adhesive formulations and coatings, particularly in indirect food additive applications where it contributes to food packaging materials.

Research Applications

Organic Synthesis: The compound serves as an important building block in organic synthesis due to its dual functionality:

• The hydroxyl group can be transformed into various other functional groups (ethers, esters, halides)
• The alkene moiety undergoes addition reactions, oxidation, and cycloaddition reactions

Sicherheit und Handhabung

According to available safety data, 3-Cyclohexene-1-methanol is not classified as a hazardous substance under standard regulations. However, proper handling procedures should always be followed.

Safety Statements:

• S23: Do not breathe vapor
• S24/25: Avoid contact with skin and eyes

When handling 3-Cyclohexene-1-methanol:

• Work in a well-ventilated area
• Avoid inhalation of vapors
• Wear appropriate personal protective equipment (gloves, goggles, lab coat)
• Store in a cool, dry place away from incompatible materials
• Follow standard laboratory safety practices

Chemische Spezifikationen

CAS-Nummer	1679-51-2
Molekulare Formel	C7H12O
Molekulargewicht	112.17 g/mol
Erscheinungsbild	Klare, farblose Flüssigkeit
Siedepunkt	Approximately 110-111°C
Dichte	Approximately 0.96 g/cm³
Functional Groups	Alkene, Primary Alcohol

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