2-Chlorostyrene

Product Introduction

2-Chlorostyrene (CAS No. 2039-87-4) is an aromatic vinyl compound consisting of a styrene backbone with a chlorine substituent at the ortho position. It is also known as o-Chlorostyrene or 1-Chloro-2-vinylbenzene.

As a reactive styrene derivative, 2-Chlorostyrene contains a polymerizable vinyl group and an aromatic chlorine substituent, making it useful as a building block for organic synthesis, polymer chemistry, functional materials, and chemical intermediate research.

Commercial 2-Chlorostyrene is commonly supplied with a small amount of inhibitor such as 4-tert-butylcatechol (TBC) to reduce unwanted polymerization during storage. TCI lists a stabilized grade with purity greater than 96% by GC, while other commercial grades are available at approximately 95–98% purity.

Mechanism / Principle

Vinyl Reactivity and Aromatic Functionalization

The vinyl group of 2-Chlorostyrene provides a reactive alkene that can participate in various organic transformations and polymerization reactions.

Its molecular structure combines:

• A reactive vinyl group
• An aromatic benzene ring
• An ortho-position chlorine substituent
• A polymerizable styrene framework

The vinyl group can undergo addition reactions, cross-metathesis, and polymerization, while the aryl chloride provides an additional functional handle for synthetic modification.

The combination of these functionalities makes 2-Chlorostyrene useful for developing functionalized aromatic compounds and polymeric materials.

Key Research Applications

1. Organic Synthesis

2-Chlorostyrene is used as a building block for preparing functionalized aromatic compounds.

Applications include:

• Organic synthesis
• Aromatic building-block research
• Synthetic intermediate development
• Alkene functionalization
• Functional aromatic compound synthesis

2. Olefin Metathesis

The vinyl group of 2-Chlorostyrene can participate in olefin metathesis reactions.

Applications include:

• Cross-metathesis
• Alkene transformation
• Functionalized alkene synthesis
• Synthetic methodology development
• Organic reaction research

Chemical databases specifically report the use of 2-Chlorostyrene in olefin cross-metathesis for the efficient synthesis of nitroalkenes.

3. Polymer Chemistry

As a styrene derivative, 2-Chlorostyrene can serve as a monomer or functional building block in polymer research.

Applications include:

• Styrenic polymer research
• Functional polymers
• Copolymer synthesis
• Polymer functionalization
• Advanced polymer materials

4. Functional Materials

The combination of the polymerizable vinyl group and aromatic chlorine functionality makes 2-Chlorostyrene useful for functional-material development.

Applications include:

• Functional polymer materials
• Aromatic polymer systems
• Materials intermediate research
• Surface-functional materials
• Specialty polymer development

5. Synthetic Intermediate Research

2-Chlorostyrene can serve as an intermediate for further chemical transformations.

Applications include:

• Pharmaceutical intermediate research
• Agrochemical intermediate research
• Fine chemical synthesis
• Specialty chemical development
• Medicinal chemistry

6. Cross-Coupling and Aryl Functionalization

The aryl chloride functionality can provide a synthetic handle for selected transition-metal-catalyzed transformations.

Applications include:

• Palladium-catalyzed coupling research
• Aryl functionalization
• C–C bond formation
• C–N bond formation
• Functional aromatic synthesis

7. Polymerization Research

The vinyl group can undergo polymerization under suitable reaction conditions.

Applications include:

• Radical polymerization
• Copolymerization
• Styrenic polymer development
• Polymer structure–property studies
• Functional monomer research

Advantages

• Reactive styrene derivative
• Contains both vinyl and aryl chloride functionalities
• Useful building block for organic synthesis
• Applicable to olefin metathesis research
• Suitable for polymer chemistry
• Useful for functional polymer development
• Applicable to aromatic functionalization
• Available in stabilized commercial grades
• Useful for synthetic intermediate research

Storage & Handling

• 2-Chlorostyrene is a reactive, flammable liquid and should be handled in accordance with its SDS.
• Commercial material is commonly supplied with TBC or another inhibitor to reduce polymerization during storage. 
• Store in a tightly closed container.
• Keep in a cool, well-ventilated area.
• Protect from heat, sparks, flames, and other ignition sources.
• Avoid unnecessary exposure to light and elevated temperatures.
• Avoid breathing vapors.
• Handle in a suitable fume hood.
• Wear appropriate gloves, protective clothing, and eye protection.
• Avoid uncontrolled polymerization.
• Consult the product-specific SDS before use.

Research Areas

Researchers working in the following fields may benefit from 2-Chlorostyrene (CAS No. 2039-87-4):

• Organic synthesis
• Polymer chemistry
• Functional polymers
• Olefin metathesis
• Materials chemistry
• Synthetic methodology
• Aromatic functionalization
• Fine chemical synthesis
• Pharmaceutical chemistry
• Specialty materials

Q1: What is 2-Chlorostyrene?

A: 2-Chlorostyrene is a chlorinated styrene derivative with CAS No. 2039-87-4, molecular formula C₈H₇Cl, and molecular weight 138.59 g/mol. It is also called o-Chlorostyrene.

Q2: What is another name for 2-Chlorostyrene?

A: Common names include o-Chlorostyrene, 1-Chloro-2-vinylbenzene, 1-Chloro-2-ethenylbenzene, and (2-Chlorophenyl)ethylene.

Q3: What is 2-Chlorostyrene used for?

A: It is used primarily as a synthetic building block, polymer research monomer, olefin-metathesis substrate, and functional aromatic intermediate.

Q4: What is the molecular weight of 2-Chlorostyrene?

A: The molecular weight is approximately 138.59 g/mol.

Q5: Is 2-Chlorostyrene stabilized?

A: Yes. Commercial grades are commonly stabilized with a small amount of an inhibitor such as 4-tert-butylcatechol (TBC). TCI lists a grade stabilized with TBC.

Q6: Is 2-Chlorostyrene a liquid?

A: Yes. Commercial specifications describe it as a clear colorless to yellow liquid.

Q7: Can 2-Chlorostyrene be used in polymer research?

A: Yes. Its vinyl group makes it suitable for research involving styrenic polymerization, copolymerization, and functional polymer materials.

Q8: What is the difference between 2-Chlorostyrene and 4-Chlorostyrene?

A: Both are chlorinated styrene derivatives, but the chlorine substituent is located at different positions on the benzene ring. 2-Chlorostyrene is the ortho isomer, while 4-Chlorostyrene is the para isomer. Their different molecular geometries can affect reactivity and material properties.