1-Chloro-3-methyl-2-butene
[CAS# 503-60-6]

Identification

• Classification: Chemical pesticide >> Insecticide intermediate
• Name: 1-Chloro-3-methyl-2-butene
• Molecular Formula: C₅H₉Cl
• Molecular Weight: 104.58
• CAS Registry Number: 503-60-6
• EC Number: 207-972-7
• SMILES: CC(=CCCl)C

Properties

• Density: 0.928
• Boiling point: 58-59 °C (120 mmHg)
• Refractive index: 1.4488
• Flash point: 4 °C

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H226-H315-H319-H335
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P280-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Flammable liquids	Flam. Liq.	2	H225
Specific target organ toxicity - single exposure	STOT SE	3	H335
Flammable liquids	Flam. Liq.	2	H226
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 1993

Discovery and Applications

1-Chloro-3-methyl-2-butene, also known as isobutyl chloride, was first synthesized and identified in the early 20th century as part of organic chemistry research. Its discovery was a result of efforts to explore the synthesis and properties of various chlorinated organic compounds. This chemical compound is characterized by a chlorine atom attached to the first carbon atom of a butene molecule, with a methyl group on the third carbon atom. Its structure and properties were elucidated through systematic chemical reactions and spectroscopic analysis, contributing to the understanding of organic chemistry principles.

1-Chloro-3-methyl-2-butene serves as a valuable intermediate in organic synthesis. It participates in various chemical reactions, including nucleophilic substitution and elimination reactions, to form complex organic molecules. It is commonly used in the production of pharmaceuticals, agrochemicals, and fine chemicals due to its versatile reactivity and ability to introduce functional groups into organic compounds.

This compound is utilized in the polymer industry for the synthesis of specialty polymers and copolymers. It acts as a monomer or comonomer in polymerization reactions, contributing to the formation of polymers with specific properties and functionalities. Its incorporation into polymer chains enhances the mechanical, thermal, and chemical properties of the resulting materials, making them suitable for various applications, including coatings, adhesives, and sealants.

1-Chloro-3-methyl-2-butene is employed as a solvent and chemical reagent in various industrial processes. It serves as a reaction medium for organic transformations, such as alkylations and acylations, in chemical synthesis. Its use as a solvent enables the dissolution and purification of organic compounds in laboratory and industrial settings. Additionally, it acts as a versatile chemical reagent for the modification of organic molecules in diverse applications.

This compound finds applications in research laboratories and academic institutions for studying organic reactions and exploring new synthetic methodologies. Chemists utilize it as a model compound to investigate reaction mechanisms and reaction kinetics. Its reactivity and structural features make it a valuable tool for advancing the understanding of organic chemistry principles and developing innovative synthetic routes.

1-Chloro-3-methyl-2-butene is employed in the synthesis of various active ingredients in pharmaceuticals and agrochemicals. It serves as a building block for the synthesis of compounds with medicinal properties, such as pharmaceutical intermediates and pesticide active ingredients. Its use in these industries contributes to the development of new drugs, crop protection agents, and agricultural chemicals.

References

1980. Reactions of carbonyl compounds in the presence of phase-transition catalysts. 4. Study of the reaction of acetoacetic ester with 1-chloro-3-methyl-2-butene in the presence of various alkaline agents. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 29(3).
DOI: 10.1007/bf00949610

1980. Reactions of carbonyl compounds in the presence of phase-transition catalysts. 6. The alkylation and ketonic decomposition of acetoacetic and prenylacetoacetic esters. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 29(3).
DOI: 10.1007/bf00949612

1981. Synthesis of cis-1,4-bifunctional derivatives of an isoprene δ-sultone. Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 30(6).
DOI: 10.1007/bf00950299