3-Methyl-2-butenal
[CAS# 107-86-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty aldehyde (containing acetal, hemiacetal)
• Name: 3-Methyl-2-butenal
• Synonyms: 3,3-Dimethylacrolein; 3-Methylcrotonaldehyde; Prenal
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.12
• CAS Registry Number: 107-86-8
• EC Number: 203-527-6
• FEMA: 3646
• SMILES: CC(=CC=O)C

Properties

• Density: 0.88
• Boiling point: 132-133 ºC
• Refractive index: 1.461-1.463
• Flash point: 33 ºC
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07 Danger
• Hazard Statements: H226-H302--H314-H317-H318-H331
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H331
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1B	H317
Acute toxicity	Acute Tox.	5	H313
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332

• Transport Information: UN 1989

Discovory and Applicatios

3-Methyl-2-butenal, also known as prenal, is an organic compound with the molecular formula C5H8O. It belongs to the family of alpha,beta-unsaturated aldehydes and is characterized by its pungent, fruity odor. The discovery of 3-Methyl-2-butenal can be traced back to early 20th-century studies on naturally occurring flavor compounds. The isolation and characterization of 3-Methyl-2-butenal were made possible through advancements in analytical techniques such as gas chromatography and mass spectrometry.

One of the primary applications of 3-Methyl-2-butenal is in the flavor and fragrance industry. Its strong, fruity odor makes it a valuable ingredient in the formulation of various flavors and perfumes. It is used to impart a fresh, fruity note to food products, beverages, and fragrances. In the food industry, it is employed in very small concentrations to enhance the flavor of baked goods, candies, and beverages. In perfumery, 3-Methyl-2-butenal contributes to the creation of complex fragrance profiles, adding a top note that enhances the overall scent experience.

3-Methyl-2-butenal serves as an important intermediate in the synthesis of pharmaceuticals and agrochemicals. Its aldehyde functional group allows it to participate in various chemical reactions, making it a useful building block for creating more complex molecules. In pharmaceutical synthesis, it is used to develop active pharmaceutical ingredients (APIs) and other medicinal compounds. In agrochemicals, it is involved in the production of herbicides, insecticides, and fungicides?

In the field of polymer and material science, 3-Methyl-2-butenal is used as a monomer or a chemical modifier to create specialized polymers. Its unsaturated structure allows it to undergo polymerization reactions, leading to the formation of polymers with unique properties. These polymers can be used in coatings, adhesives, and other advanced materials that require specific mechanical, thermal, or chemical properties.

3-Methyl-2-butenal is also used in chemical research as a model compound to study the behavior of alpha,beta-unsaturated aldehydes. Its well-defined structure and reactivity provide a basis for investigating reaction mechanisms, kinetics, and the effects of various catalysts.

References

2023. The theoretical study of the oxidation reaction of hydroxyl radical for the removal of volatile organic aliphatic and aromatic aldehydes from the atmosphere. Structural Chemistry.
DOI: 10.1007/s11224-022-02120-w

2023. Larvae of Sasakia charonda (Lepidoptera: Nymphalidae: Apaturinae) and three related species use oral odorants to repel ants and wasps. Chemoecology.
DOI: 10.1007/s00049-023-00391-1

2024. Inhibition of undesirable flavor compounds and lipid oxidation in infant nutrition powder using kiwifruit powder, orange powder and quinoa flour-based formulations. Journal of Food Measurement and Characterization.
DOI: 10.1007/s11694-024-02507-9