Chloromethylstyrene (CMS), also known as vinylbenzyl chloride (VBC), is a reactive styrenic monomer supplied as a mixture of positional isomers. The molecule combines a polymerizable vinyl group with benzylic chloromethyl (-CH2Cl) functionality, allowing incorporation into styrenic polymers while retaining a reactive handle for subsequent chemical modification.
Synonyms: CMS; VBC; Vinylbenzyl chloride; (Chloromethyl)styrene.
The benzyl chloride functionality can undergo nucleophilic substitution after polymerization, including reaction with tertiary amines to introduce quaternary ammonium groups. This combination of polymerizable and post-functionalizable groups makes chloromethylstyrene useful in functional polymer synthesis, derivatizable polymer supports, and ion-exchange material research.
Chemical purity is ≥ 97%, with approximately 500 ppm t-butylcatechol inhibitor. Cat. 02718 is a positional-isomer mixture and should not be treated as pure 4-(chloromethyl)styrene when selecting materials or interpreting experimental results.
Key Properties
- Reactive styrenic monomer with benzylic chloromethyl functionality
- Chemical purity: ≥ 97%
- CAS Number: 30030-25-2
- Molecular formula: C9H9Cl
- Linear formula: H2C=CHC6H4CH2Cl
- Molecular weight: 152.6 g/mol
- Appearance: light yellow to colorless liquid
- Inhibitor: approximately 500 ppm t-butylcatechol
- Refractive index: 1.57
- Catalog number: 02718
- Package sizes: 100 g and 500 g
Applications
Functional Polymer & Copolymer Synthesis
Chloromethylstyrene is used as a reactive styrenic monomer in polymer and copolymer synthesis. Polymerization incorporates the vinyl group into the polymer backbone while pendant benzyl chloride functionality can remain available for subsequent derivatization.
Merrifield-Type Resins & Functional Polymer Supports
Chloromethylstyrene is used as a building block for styrenic resins bearing reactive benzyl chloride groups, including Merrifield-type polymer supports. The chloromethyl functionality provides sites that can be converted to other functional groups through post-polymerization reactions.
Anion-Exchange Resins & Membranes
Vinylbenzyl chloride-derived polymers can be reacted with suitable amines to convert benzyl chloride groups into quaternary ammonium functionality. This approach is used in research involving anion-exchange resins and anion-exchange membrane materials.
Graft & Controlled Polymerization Research
Vinylbenzyl chloride has been used in graft and block copolymer synthesis, including controlled radical polymerization approaches such as RAFT. These methods provide routes to polymer architectures that retain chloromethyl groups for subsequent chemical modification.
Compatibility & Bonding Considerations
- The styrenic vinyl group supports radical polymerization and copolymerization under appropriately selected conditions
- The benzylic chloromethyl group provides a reactive site for post-polymerization nucleophilic substitution
- Reaction with suitable tertiary amines can introduce quaternary ammonium functionality into chloromethylstyrene-derived polymers
- Contains approximately 500 ppm t-butylcatechol inhibitor, which should be considered when establishing polymerization conditions
- Crosslinked styrenic networks may be prepared by copolymerization with an appropriate multifunctional comonomer such as divinylbenzene
- Cat. 02718 is an isomer mixture and should not be treated as a pure para-isomer material
Final polymer properties and functionalization levels depend on monomer composition, comonomer selection, molecular weight, conversion, crosslink density, and subsequent derivatization conditions.
Application Tips
- Account for the approximately 500 ppm t-butylcatechol inhibitor when establishing polymerization conditions
- Maintain consistent initiator concentration, temperature, oxygen control, and comonomer composition when comparing polymerization results
- When the chloromethyl groups are required for subsequent functionalization, characterize functional-group retention after polymerization rather than assuming complete preservation
- For quaternization or other nucleophilic substitution reactions, evaluate reaction conditions and degree of substitution under the intended polymer and solvent system
- Quantify ion-exchange capacity or functionalization experimentally when preparing ion-exchange materials rather than inferring conversion solely from monomer feed composition
Handling & Storage
- Store at 4°C in a cool, well-ventilated location
- Store securely and keep the material protected from inappropriate access
- Handle in a chemical fume hood or other adequately ventilated area
- Avoid breathing mist, vapor, or spray and avoid contact with skin and eyes
- Wear protective gloves, safety glasses, and suitable protective clothing during handling
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FAQ
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1. What is chloromethylstyrene used for?
Chloromethylstyrene is a reactive styrenic monomer used in functional polymer and copolymer synthesis. Its benzyl chloride groups provide sites for subsequent chemical modification, including preparation of functional polymer supports, ion-exchange resins, and anion-exchange membrane materials.
2. Are chloromethylstyrene and vinylbenzyl chloride the same material?
Vinylbenzyl chloride (VBC) is a commonly used name for chloromethylstyrene. Cat. 02718 is supplied as a mixture of chloromethylstyrene positional isomers with CAS Number 30030-25-2.
3. Is Cat. 02718 pure 4-(chloromethyl)styrene?
No. Cat. 02718 is a mixture of chloromethylstyrene positional isomers and should not be treated as pure 4-(chloromethyl)styrene. The current specification defines the material as an isomer mixture with ≥ 97% assay.
4. Why is the chloromethyl group useful in polymer synthesis?
The benzylic chloromethyl group provides a reactive handle for post-polymerization modification. It can undergo nucleophilic substitution with compatible reagents, including reactions with tertiary amines that introduce quaternary ammonium functionality into the polymer.
5. What purity, inhibitor, and package sizes are available?
Cat. 02718 has a chemical purity of ≥ 97% and contains approximately 500 ppm t-butylcatechol inhibitor. It is available in 100 g and 500 g packages. For larger quantities, use the bulk-quote option.
Safety & Documentation
Chloromethylstyrene is corrosive, is harmful in contact with skin, and can cause severe skin burns and eye damage. Use appropriate laboratory ventilation and personal protective equipment. Refer to the product Safety Data Sheet (SDS) for complete handling, storage, first-aid, transport, and disposal guidance.
