2-Methyl-4-penten-2-ol
[CAS# 624-97-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 2-Methyl-4-penten-2-ol
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• CAS Registry Number: 624-97-5
• EC Number: 620-963-6
• SMILES: CC(C)(CC=C)O

Properties

• Density: 0.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.430, Calc.^*
• Boiling Point: 119.5±0.0 °C (760 mmHg), Calc.^*
• Flash Point: 41.3±8.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 1993

Discovery and Applications

2-Methyl-4-penten-2-ol is a chemical compound that belongs to the family of alcohols, specifically an allyl alcohol derivative. It is characterized by its molecular structure, which consists of a five-carbon chain with a hydroxyl group (-OH) attached to the second carbon and a methyl group (-CH3) at the second position. This structure places it in the class of unsaturated alcohols, which are known for their versatility in both synthetic chemistry and industrial applications.

The discovery of 2-methyl-4-penten-2-ol likely arose from studies into the properties and reactivity of alkyl-substituted unsaturated alcohols. These compounds are of interest due to their ability to participate in a wide range of chemical reactions, such as nucleophilic substitution, condensation, and cyclization. The compound itself may have been identified during research into the development of novel organic intermediates or as part of investigations into the reactivity of pentenol derivatives. Its structure provides it with unique reactivity, allowing it to serve as a building block in various synthetic processes.

One of the primary applications of 2-methyl-4-penten-2-ol is in the synthesis of fine chemicals and intermediates used in the fragrance and flavor industries. Due to the presence of the unsaturated bond and the hydroxyl group, it exhibits a distinctive reactivity that makes it useful in the production of various functionalized derivatives. These derivatives can be employed in the design of molecules with specific scents or flavors, contributing to the creation of new compounds for use in food, cosmetics, and other consumer products.

In addition to its applications in the flavor and fragrance industry, 2-methyl-4-penten-2-ol is also valuable in the field of organic synthesis. It can be used as a starting material in the synthesis of more complex molecules, particularly in the production of cyclized structures or molecules with extended conjugation systems. The compound’s double bond allows it to undergo reactions such as electrophilic addition and Michael additions, which are important strategies in the creation of larger, more complex organic frameworks. As a result, 2-methyl-4-penten-2-ol is often used as an intermediate in the development of pharmaceuticals, agrochemicals, and other specialized organic compounds.

Moreover, 2-methyl-4-penten-2-ol is utilized in the synthesis of certain polymers and resins. It can act as a monomer or co-monomer in polymerization reactions, where its unique structure contributes to the formation of materials with specific physical or chemical properties. Polymers produced from such monomers may possess enhanced mechanical strength, flexibility, or chemical resistance, making them suitable for a variety of industrial applications.

The compound’s potential biological activity is another area of interest. Alcohols, particularly unsaturated alcohols like 2-methyl-4-penten-2-ol, have been studied for their potential as bioactive compounds. In particular, some studies suggest that this compound may possess antimicrobial, antioxidant, or anti-inflammatory properties, although further research is needed to fully understand its biological effects and therapeutic potential. As a result, researchers have investigated its possible applications in the pharmaceutical industry, where it may be developed into a lead compound for further drug discovery.

In conclusion, 2-methyl-4-penten-2-ol is a versatile and valuable compound with applications across multiple industries, including flavor and fragrance, organic synthesis, polymer chemistry, and potentially pharmaceuticals. Its unique structural features, including an unsaturated bond and hydroxyl group, allow it to participate in a variety of chemical reactions, making it a useful intermediate in the synthesis of more complex organic molecules. The continuing exploration of its properties and applications suggests that 2-methyl-4-penten-2-ol will remain an important compound in both industrial and research settings.

References

2017. Reactions of Allylmagnesium Halides with Carbonyl Compounds: Reactivity, Structure, and Mechanism. Synthesis, 49(17).
DOI: 10.1055/s-0036-1588427

2019. Asymmetric Kulinkovich Hydroxycyclopropanation of Alkenes Mediated by Titanium(IV) TADDOLate Complexes. Synthesis, 51(06).
DOI: 10.1055/s-0037-1611709