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Send EmailChloromethyl Allyltrichloro Silane, Trichloro Chloromethyl allylsilane, 1871-57-4
Product Name: 2-(Chloromethyl)allyltrichlorosilane
Chemical Name: 2-(Chloromethyl)allyltrichlorosilane
CAS No: 1871-57-4
EC No (EINECS): 217-489-3
Chemical Formula: C₄H₆Cl₄Si
Molecular Weight: 223.99 g/mol
REACH Status: Registered
| Parameter | Description |
|---|---|
| Chemical Name (IUPAC) | Trichloro[2-(chloromethyl)prop-2-en-1-yl]silane |
| Other Names | 2-(Chloromethyl)allyltrichlorosilane, 2-(Chloromethyl)allyltrichlorosilane, Trichloro(2-(chloromethyl)allyl)silane |
| CAS Number | 1871-57-4 |
| EC Number (EINECS) | 217-489-3 |
| Molecular Formula | C₄H₆Cl₄Si |
| Molecular Weight | 223.99 g/mol |
| Chemical Class | Organochlorosilane, functional silane |
| Appearance | Colorless to straw-colored liquid |
| Odor | Sharp HCl odor |
| Taste | Not determined as technical product |
| REACH Status | Registered |
CHEMICAL STRUCTURE AND DESCRIPTION:
2-(Chloromethyl)allyltrichlorosilane is an organochlorosilane containing an allyl group with a chloromethyl substituent and three chlorine atoms bonded to the silicon atom. Its structure contains both reactive chlorosilane groups and an allylic double bond and chloromethyl group. This structure gives the product high reactivity and versatile functionality.
Structural Formula (Open Structure):
Cl₃Si-CH₂-C(Cl)=CH₂
(Trichloro[2-(chloromethyl)prop-2-en-1-yl]silane)
These structural features:
Give the product three hydrolyzable Si-Cl bonds.
Allow polymerization and addition reactions due to the allylic double bond.
Provide a reactive site for nucleophilic substitution reactions via the chloromethyl group.
Enable its use as a crosslinker in silane surface modification, adhesives, and coatings.
2-(Chloromethyl)allyltrichlorosilane is a reactive organochlorosilane used as a silane coupling agent, surface modifier, crosslinker in adhesive and coating formulations, and as an intermediate in organic syntheses.
| Property | Value |
|---|---|
| Molecular Formula | C₄H₆Cl₄Si |
| Molecular Weight | 223.99 g/mol |
| Appearance | Colorless to straw-colored liquid |
| Odor | Sharp HCl odor |
| Density | 1.35 g/cm³ (20 °C) |
| Boiling Point | ~110 °C (75 mmHg) |
| Flash Point | >65 °C (closed cup) |
| Vapor Pressure | Low (<1 mmHg at 20 °C) |
| Solubility | Reacts rapidly with water; soluble in inert organic solvents |
| Stability | Stable when protected from moisture; hydrolyzes with water |
| pH (aqueous solution) | Acidic (releases HCl) |
| Volatility | Moderate |
| Hygroscopicity | May absorb moisture; store in dry conditions |
2-(Chloromethyl)allyltrichlorosilane is a colorless to straw-colored liquid. Its density is 1.35 g/cm³ (20 °C), boiling point ~110 °C (75 mmHg), flash point >65 °C. It reacts rapidly with water to release HCl. It must be protected from moisture.
| Solvent | Solubility | Conditions |
|---|---|---|
| Water | Reacts (hydrolysis) | 20 °C |
| Methanol | Reacts | - |
| Ethanol | Reacts | - |
| Acetone | Soluble | - |
| Ethyl acetate | Soluble | - |
| Hexane | Soluble | - |
| Toluene | Soluble | - |
| Xylene | Soluble | - |
| Dichloromethane | Soluble | - |
| Glycols | Reacts | - |
The product reacts with polar protic solvents (water, alcohols). It is soluble in aprotic organic solvents (hexane, toluene, acetone). This property makes it suitable for applications requiring anhydrous conditions.
| Property | Description |
|---|---|
| Chemical Class | Organochlorosilane |
| Reactivity | Hydrolysis, condensation, addition, substitution |
| Hydrolytic Stability | Low; hydrolyzes rapidly with water |
| Thermal Stability | Moderate |
| Oxidation Resistance | Moderate |
| Polymerization | Can be polymerized under controlled conditions |
| Compatibility | Organic solvents, silanes, polymers |
| Substances to Avoid | Water, moisture, alcohols, strong oxidizing agents, bases |
| Hazardous Decomposition Products | Hydrogen chloride (HCl), chlorosilanes, carbon monoxide (CO), carbon dioxide (CO₂) |
Due to its Si-Cl bonds, the product hydrolyzes rapidly with water and moisture, releasing HCl. Hydrolysis produces silanol intermediates, which can condense to form siloxane bonds. The allylic double bond can participate in free-radical or addition reactions. The chloromethyl group is open to nucleophilic substitution reactions.
| Parameter | Specification |
|---|---|
| Purity (GC) | ≥ 97.0% |
| Appearance | Colorless to straw-colored liquid |
| Color (Pt-Co) | ≤ 50 Hazen |
| Water Content | ≤ 0.1% |
| Acid Value (HCl) | ≤ 0.1 mg KOH/g |
| Density (20 °C) | 1.34–1.36 g/cm³ |
| Boiling Range | 105–115 °C (75 mmHg) |
| Flash Point | ≥ 65 °C |
| Refractive Index (20 °C) | 1.470–1.480 |
| Heavy Metals | ≤ 10 ppm |
| Shelf Life | 12 months (under proper storage) |
The product is produced in technical grade with high purity. Protection from moisture is critical. In industrial applications, batch-to-batch consistency and low impurity content are important.
| Application | Description |
|---|---|
| Surface Modification | Modification of glass, metal, and mineral surfaces |
| Composites | Strengthens polymer-inorganic interface bonding |
| Fillers | Treatment of silica, glass fiber, and clay surfaces |
| Adhesives | Increases adhesion strength |
The product forms strong bonds between surfaces and the polymer matrix as a silane coupling agent.
| Application | Description |
|---|---|
| Crosslinker | Provides crosslinking in polymer systems |
| Adhesion Promoter | Increases adhesion of coatings to surfaces |
| Coatings | Provides chemical and thermal resistance |
| Sealants | Provides flexibility and strength |
The product is used as a crosslinker and adhesion promoter.
| Application | Description |
|---|---|
| Functional Silanes | In the synthesis of other functional silanes |
| Polymer Modification | Imparts silane functionality to polymers |
| Pharmaceutical Intermediates | Intermediate in drug synthesis |
| Agrochemical Synthesis | Pesticide and herbicide intermediates |
The product is used as a reactive intermediate in organic syntheses.
| Application | Description |
|---|---|
| Surface Treatment | Hydrophobic treatment of glass and metal surfaces |
| Rubber | Adhesion and strength enhancer in rubber compounds |
| Electronics | Modification of semiconductor surfaces |
| Textiles | Functionalization of textile surfaces |
| Property | Description |
|---|---|
| Structural Class | Organochlorosilane |
| Functional Groups | Si-Cl (three), allylic double bond, chloromethyl |
| Hydrolysis Sensitivity | High |
| Reactivity | High |
| Polymerization Ability | Via allylic double bond |
| Surface Activity | High |
| Polarity | Medium–high |
| Evaporation Profile | Moderate, controlled |
The three Si-Cl bonds provide high hydrolysis reactivity and surface bonding ability. The allylic double bond allows for polymerization and addition reactions.
| Application | Description |
|---|---|
| Hydrolysis | Reacts with water to form silanol and HCl |
| Condensation | Silanol groups form siloxane bonds |
| Addition | Addition reactions via the allylic double bond |
| Substitution | Nucleophilic substitution via the chloromethyl group |
| Surface Modification | Forms covalent bonds with surfaces |
| Polymerization | Can be polymerized under controlled conditions |
| Parameter | Value |
|---|---|
| GHS Classification | Flam. Liq. 3 (H226), Skin Corr. 1B (H314), Eye Dam. 1 (H318), Acute Tox. 3 (H331), STOT SE 3 (H335), Aquatic Acute 1 (H400), Aquatic Chronic 1 (H410) |
| Oral LD50 (Rat) | ~500 mg/kg (estimated) |
| Dermal LD50 (Rabbit) | ~200 mg/kg (estimated) |
| Skin Irritation | Causes severe skin burns (H314) |
| Eye Irritation | Causes serious eye damage (H318) |
| Respiratory Irritation | Fatal if inhaled (H331); respiratory tract irritation (H335) |
| Skin Sensitization | Not expected |
| Mutagenicity | Not classified |
| Carcinogenicity | Not classified |
| Bioaccumulation | Not likely |
| WGK Germany | 3 (very hazardous to water) |
The product is a flammable, toxic, and corrosive chemical. It causes severe burns on contact with skin and eyes. It may be fatal if inhaled. It is very toxic to aquatic life. Appropriate PPE must be used in industrial handling.
| Parameter | Information |
|---|---|
| UN Number | UN 2986 (Chlorosilanes, corrosive, flammable, water-reactive) |
| Hazard Class | 8 (Corrosive substances) / 3 (Flammable liquids) |
| Packing Group | II |
| Proper Shipping Name | Chlorosilanes, corrosive, flammable, n.o.s. (2-(Chloromethyl)allyltrichlorosilane) |
| Marine Pollutant | Yes |
| ADR/RID Label | Class 8 (3) |
| Transport Regulations | Must be transported in accordance with ADR/RID/IMDG/IATA rules |
The product is classified as a corrosive and flammable liquid. It belongs to the water-reactive substances category. Transport must comply with ADR/RID/IMDG/IATA regulations.
| Region | Status |
|---|---|
| EU | REACH registered |
| USA (TSCA) | Listed |
| EINECS | 217-489-3 |
| Turkey (KKDİK) | Should be evaluated within compliance and registration requirements |
| Food Contact | Not suitable for technical grade |
| Hazardous Substance | Yes (flammable, toxic, corrosive, environmentally hazardous) |
| Parameter | Information |
|---|---|
| Storage Conditions | In a well-ventilated, cool and dry area, in tightly closed containers |
| Temperature | 15–25 °C |
| Container Requirements | Moisture-proof, tightly closed containers |
| Moisture Control | Protect from moisture; storage under inert gas is recommended |
| Substances to Avoid | Water, moisture, alcohols, strong oxidizing agents, bases, ignition sources |
| Shelf Life | 12 months (under proper storage) |
| Handling Notes | Avoid breathing vapor; use PPE; work in anhydrous conditions |
| Packaging Options | 25 kg, 200 kg drums; custom packaging upon request |
Handling Notes:
Avoid breathing vapor.
Use appropriate personal protective equipment (gloves, goggles, mask, protective clothing).
Avoid contact with skin and eyes.
Keep away from ignition sources.
Protect from moisture; work under inert atmosphere.
| Parameter | Information |
|---|---|
| Fire Hazard | Flammable liquid; vapor/air mixture may be flammable |
| Flash Point | >65 °C (closed cup) |
| Extinguishing Media | Water spray, foam, CO₂, dry chemical powder |
| Special Hazards | Thermal decomposition may release HCl, organic acid vapors, CO, CO₂ |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
The product is a flammable liquid. In case of fire, appropriate extinguishing media should be used, and firefighting personnel should wear protective equipment. It reacts with water to release HCl.
| Parameter | Information |
|---|---|
| Personal Protection | Respirator, protective goggles, gloves, protective clothing |
| Ventilation | Ventilate the area |
| Containment | Contain the spill |
| Cleaning Methods | Absorb with inert material (clay, vermiculite); place in suitable disposal container |
| Environmental Precautions | Prevent entry into drains, sewers, and water sources |
| Waste Disposal | Hydrolyze with water and neutralize HCl; incinerate the organic phase |
In case of a spill, clean up while preventing vapor formation. Do not allow contact with water. Dispose of waste properly. Prevent environmental release.
| Exposure Route | Action |
|---|---|
| Inhalation | Move to fresh air, administer artificial respiration if necessary, seek immediate medical attention |
| Skin Contact | Wash with plenty of water and soap, remove contaminated clothing, seek medical attention |
| Eye Contact | Rinse with water for at least 15 minutes, seek immediate medical attention |
| Ingestion | Do not induce vomiting, rinse mouth, seek immediate medical attention |
| Raw Material | Description |
|---|---|
| Allyl chloride | Precursor in synthesis |
| Trichlorosilane | Silicon source |
| Chloromethyl derivatives | Functional group source |
| Catalyst | Hydrosilylation catalyst (Pt-based) |
| By-Product | Application |
|---|---|
| Functional Silanes | Surface modification, coupling agent |
| Siloxane Polymers | Coatings, sealants |
| Adhesives and Coatings | Crosslinker, adhesion promoter |
| Organic Synthesis Intermediates | Pharmaceutical, agrochemical |
| Industry | Application Area | Example Use | Suitability |
|---|---|---|---|
| Composites | Silane coupling agent | Glass fiber, fillers | High |
| Adhesives | Crosslinker, adhesion promoter | Industrial adhesives | High |
| Coatings | Surface modification | Chemical-resistant coatings | High |
| Rubber | Adhesion enhancer | Rubber compounds | Suitable |
| Electronics | Surface modification | Semiconductor surfaces | Suitable |
| Organic Synthesis | Intermediate | Functional silane synthesis | High |
The product can undergo many chemical reactions due to its three Si-Cl bonds and allylic double bond:
| Reaction | Description |
|---|---|
| Hydrolysis | Reacts with water to form silanol and HCl |
| Condensation | Silanol groups form siloxane bonds |
| Addition | Addition reactions via the allylic double bond |
| Substitution | Nucleophilic substitution via the chloromethyl group |
| Grignard Reaction | Reaction with organomagnesium compounds |
| Polymerization | Can be polymerized under controlled conditions |
The product derivatives are widely used in composites, adhesives, coatings, and organic synthesis.
| Compound | Description |
|---|---|
| Allyltrichlorosilane | Similar structure; contains allyl group |
| Chloromethyltrichlorosilane | Similar structure; contains chloromethyl group |
| Vinyltrichlorosilane | Similar structure; contains vinyl group |
| 3-Chloropropyltrichlorosilane | Similar structure; contains chloropropyl group |
| Methacryloxypropyltrichlorosilane | Similar structure; methacrylate-functional |
| Silane Coupling Agents | Silanes used for surface modification |
SUMMARY:
2-(Chloromethyl)allyltrichlorosilane is a colorless to straw-colored liquid with the formula C₄H₆Cl₄Si and CAS number 1871-57-4. It is a reactive organochlorosilane containing three Si-Cl bonds, an allylic double bond, and a chloromethyl group. It is used as a silane coupling agent, surface modifier, crosslinker in adhesive and coating formulations, and as an intermediate in organic syntheses. It reacts rapidly with water to release HCl. It is a flammable, toxic, and corrosive chemical; it causes severe burns to skin and eyes. It may be fatal if inhaled. It is very toxic to aquatic life. It should be stored in a cool, dry, and well-ventilated area in tightly closed containers, protected from moisture.
Key Properties:
| Property | Value |
|---|---|
| Appearance | Colorless to straw-colored liquid |
| Chemical Formula | C₄H₆Cl₄Si |
| Molecular Weight | 223.99 g/mol |
| CAS Number | 1871-57-4 |
| Boiling Point | ~110 °C (75 mmHg) |
| Density | 1.35 g/cm³ (20 °C) |
| Flash Point | >65 °C (closed cup) |
| Water Solubility | Reacts (hydrolysis) |
| Chemical Class | Organochlorosilane |
| Primary Use | Silane coupling agent, surface modification, crosslinker |
Main Applications:
| Industry | Applications |
|---|---|
| Composites | Silane coupling agent, surface modification |
| Adhesives | Crosslinker, adhesion promoter |
| Coatings | Surface modification, chemical resistance |
| Rubber | Adhesion enhancer |
| Electronics | Surface modification |
| Organic Synthesis | Intermediate |
Key Safety Points:
FLAMMABLE: Flam. Liq. 3 (H226)
CORROSIVE: Skin Corr. 1B (H314), Eye Dam. 1 (H318)
TOXIC: Acute Tox. 3 (H331) – fatal if inhaled
RESPIRATORY IRRITATION: STOT SE 3 (H335)
VERY TOXIC TO AQUATIC LIFE: Aquatic Acute 1 (H400), Aquatic Chronic 1 (H410)
STORAGE: 15–25 °C, cool, dry, well-ventilated, protected from moisture
PPE RECOMMENDED: Gloves, protective goggles, respirator, protective clothing
INCOMPATIBLE: Water, moisture, alcohols, strong oxidizing agents, bases, ignition sources
CRITICAL WARNINGS:
The product is a reactive organochlorosilane containing three Si-Cl bonds. It reacts rapidly with water to release HCl.
It forms strong bonds between surfaces and the polymer matrix as a silane coupling agent.
It can participate in polymerization and addition reactions due to the allylic double bond.
The chloromethyl group provides a reactive site for nucleophilic substitution reactions.
It is a flammable liquid; it should be kept away from ignition sources.
It is a toxic and corrosive chemical; it causes severe burns to skin and eyes.
It may be fatal if inhaled; breathing vapor should be avoided.
It is very toxic to aquatic life; environmental release must be prevented.
It must be protected from moisture; storage under inert atmosphere is recommended.
Important Statement: This Technical Data Sheet (TDS) is for informational purposes only. The information provided is based on available data and is believed to be accurate. However, the user is solely responsible for determining the suitability of the product for their own specific applications and for complying with all applicable regulations and safety requirements. For complete safety, use, storage, and regulatory compliance information, always refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. Users are obligated to test the product in their own processes and applications. All local, national, and international regulations must be followed when working with 2-(Chloromethyl)allyltrichlorosilane.