3-Methyl-2-buten-1-ol
[CAS# 556-82-1]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 3-Methyl-2-buten-1-ol
• Synonyms: 3,3-Dimethylallyl alcohol; Prenyl alcohol
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• CAS Registry Number: 556-82-1
• EC Number: 209-141-4
• SMILES: CC(=CCO)C

Properties

• Density: 0.848
• Boiling point: 140 °C
• Refractive index: 1.442-1.444
• Flash point: 43 °C
• Water solubility: 170 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS07 Danger
• Risk Statements: H226-H302--H314-H315-H318-H319
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P330-P332+P317-P337+P317-P362+P364-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	1B	H350
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1987

Discovery and Applications

3-Methyl-2-buten-1-ol, also known as isoprenol, was first discovered through organic chemistry research. It is derived from the isoprene molecule and can be synthesized through various chemical processes, including hydration of isoprene or isomerization of prenol. This compound's discovery dates back to the early 20th century, with its structure confirmed through spectroscopic analysis and chemical characterization techniques. Isoprenol's unique structure and chemical properties make it a valuable compound for various applications across different industries.

Isoprenol serves as a versatile building block in organic synthesis. It participates in reactions to produce various compounds such as fragrances, flavors, and pharmaceutical intermediates. Its chemical reactivity allows for the formation of complex molecules with specific functionalities.

Isoprenol is utilized in the fragrance and flavor industry as a precursor for the synthesis of aroma compounds. It contributes to the formulation of perfumes, colognes, and food flavorings, imparting pleasant scents and tastes to consumer products.

Isoprenol is used in the production of polymers and resins. It serves as a monomer in polymerization reactions to produce materials with desired properties such as elasticity, durability, and thermal stability. These polymers find applications in various industries, including automotive, construction, and packaging.

Isoprenol finds applications in pharmaceuticals as a starting material for the synthesis of pharmaceutical compounds. It is used in the production of drugs targeting cardiovascular diseases, cancer treatments, and antiviral medications.

Isoprenol is utilized as a solvent in various chemical processes and as an intermediate in the synthesis of specialty chemicals. Its solvency properties make it suitable for dissolving and transporting various substances, while its chemical reactivity enables the production of diverse chemical compounds.

References

2024. Aroma Alchemy: Uridine diphosphate-dependent glycosyltransferases mediated regulation of fruit aroma and flavor biosynthesis. Phytochemistry Reviews.
DOI: 10.1007/s11101-024-10049-7

2024. Engineering Escherichia coli via introduction of the isopentenol utilization pathway to effectively produce geranyllinalool. Microbial Cell Factories, 23(1).
DOI: 10.1186/s12934-024-02563-2

2024. Metabolic engineering of terpene metabolism in lavender. Beni-Suef University Journal of Basic and Applied Sciences, 13(1).
DOI: 10.1186/s43088-024-00524-7