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Tert-Butylchlorodiphenylsilane is an important organic silicon compound. Its molecular formula is C16H19ClSi and its molecular weight is 274.86. Its structure consists of one tert butyl group (- C (CH3) 3), two phenyl groups (- C6H5), and one chlorosilyl group (- SiCl). This unique structure gives tert butyldiphenylchlorosilane special reactivity and selectivity in organic synthesis. The appearance is usually a colorless to pale yellow or slightly brown liquid, which is irritating and corrosive.
At 25 ° C, its density is 1.057g/mL, indicating that it has a certain weight. But it is sensitive to moisture and easily undergoes hydrolysis reactions with water, producing corresponding alcohols and silicic acid. Therefore, it is necessary to keep it dry during storage and use. Used as a protective agent in organic synthesis, pharmaceutical intermediate synthesis, benzothiazole synthesis, as well as in the preparation of silicon-based ethers and crosslinking agents for high molecular weight polymers.
Additional information of chemical compound:
|
Chemical Formula |
C16H19ClSi |
|
Exact Mass |
274.09 |
|
Molecular Weight |
274.86 |
|
m/z |
274.09(100.0%),276.09(32.0%),275.10(17.3%),277.09(5.5%),275.09(5.1%),276.09(3.3%),277.09(1.6%),276.10(1.4%),278.09(1.1%) |
|
Elemental Analysis |
C, 69.92; H, 6.97; Cl, 12.90; Si, 10.22 |
|
Boiling point |
90℃0.01 mm Hg(lit.) |
|
Density |
1.057 g/mL at 25℃(lit.) |
|
Storage conditions |
2-8℃ |
 |
 |
Special Applications and Case Studies
As a highly efficient silane protectant, tert-butyldiphenylchlorosilane (CAS No. 58479-61-1), with its unique chemical properties, shows irreplaceable value in the fields of organic synthesis, drug development, and modification of polymer materials. From the core application scenarios and typical cases, we will analyze its technical advantages and industry impact.
Drug synthesis: a "precise shield" to protect groups
In the construction of drug molecules, hydroxyl, carboxyl, amino and other active groups are susceptible to side reactions during the reaction, leading to a decrease in the yield of the target product. Tert-butyldiphenylchlorosilane replaces the hydrogen atoms of these groups with silyl groups to form stable silyl ether or silyl amine intermediates, which makes the target groups "invisible" in the subsequent reaction, and then hydrolyzes to remove the protective groups and restore the original activity after the key steps are completed.
Case: Synthesis of Fluvastatin Sodium
Fluvastatin sodium is a statin drug used to lower cholesterol, and its synthetic pathway requires protection of the alcohol hydroxyl group. The traditional method uses trimethylsilyl chloride (TMSCl), but there are problems such as easy to fall off the protective group and poor reaction selectivity. After switching to tert-butyldiphenylchlorosilane:
Protective stage: In tetrahydrofuran solvent, the alcohol hydroxyl group reacts with TBDPSCl to form silyl ether (TBDPS-O-R), which blocks the hydroxyl group activity.
Intermediate reaction: In the protected state, oxidation, esterification or cyclization of other parts of the molecule are carried out to avoid hydroxyl group interference.
Deprotection stage: After the reaction is completed, the Si-O bond is broken by acidic hydrolysis to release the original hydroxyl group, and the target product yield is increased from 65% to 82% with 99.5% purity.
This process significantly reduces the generation of by-products, shortens the synthesis cycle, and becomes the key technology for industrialized production.
Polymer material modification: rubber performance of the "molecular switch"
Solubilized styrene butadiene rubber (SSBR) due to the high activity of the end of the molecular chain, prone to oxidative degradation or chain transfer reaction, resulting in reduced material strength, increased rolling resistance. Tert-butyl diphenylchlorosilane can precisely regulate the molecular structure of rubber and improve its performance through end-capping modification.
Case: Preparation of high-performance tire rubber
A joint study by Qingdao University of Science and Technology and Beijing University of Chemical Technology showed that TBDPSCl was used to modify SSBR by capping:
Optimization of capping conditions: Reaction at 60℃ for 70 minutes, capping ratio up to 2.0, capping rate up to 77.2%.
Performance enhancement:
Mechanical properties: 15% increase in tensile strength and 20% increase in elongation at tear.
Dynamic performance: dynamic compression temperature rise is reduced by 12%, rolling resistance is reduced by 10%, which significantly improves the fuel economy and abrasion resistance of tires.
Structural modulation: By converting the chain end group from styrene to butadiene, the capping efficiency is further improved, providing new ideas for customized rubber design.
The technology has been applied to the product upgrading of Michelin, Bridgestone and other tire companies, promoting the industry's transition to low-carbon.
Biomedicine: "Targeted Anchors" for Molecular Probes
In biosensing technology, biotin needs to be labeled onto proteins or nucleic acids to achieve specific detection. Tert-butyldiphenylchlorosilane improves labeling efficiency by protecting the carboxyl group from premature activation in the coupling reaction.
Case: Synthesis of probes for tumor marker detection
A research team used TBDPSCl to develop highly sensitive biotinylated probes:
Protection of carboxyl group: TBDPSCl is used to protect the carboxyl group in the biotin molecule, preventing its early activation in the coupling reaction.
Targeting modification: In the protected state, the biotin is attached to an antibody or aptamer to form a targeting module.
Deprotection and activation: after hydrolysis to remove the silyl groups, the exposed carboxyl groups can be covalently bound to fluorescent markers or magnetic particles to construct probes.
This strategy has been successfully applied to prostate-specific antigen (PSA) detection with a detection limit as low as 0.1 pM, providing a new tool for early cancer diagnosis.
Material Surface Functionalization: Invisible Coating for Metal Corrosion Prevention
Tert-butyldiphenylchlorosilane can be used to form a hydrophobic silicone-based coating on the surface of a material through the sol-gel method, giving the substrate self-cleaning and corrosion-resistant properties.
Case: Development of anti-corrosion coatings for aluminum alloys
A team blended TBDPSCl with ethyl orthosilicate (TEOS) to prepare a superhydrophobic coating on the surface of aluminum alloys:
Coating performance: contact angle up to 158°, rolling angle less than 5°, showing excellent self-cleaning ability.
Corrosion resistance: after 720 hours of immersion in 3.5% NaCl solution, the coating remains intact and the corrosion rate is reduced by 90%.
Application prospects: the technology has been expanded to ships, aviation and other fields, significantly extending the service life of metal structures.
Research and Development Background and Opportunity (Early 1970s)
In the 1970s, organic synthesis entered a peak period for the construction of complex molecules such as nucleosides, carbohydrates, and natural products. The selective protection and mild deprotection of hydroxyl groups became a critical challenge. Although tert-butyldimethylsilyl chloride (TBDMSCl) developed by Corey and others had been widely used, it suffered from drawbacks including insufficient stability under acidic conditions and limited selectivity for primary/secondary hydroxyl groups. Organic chemists were in urgent need of more stable and highly selective silane protecting reagents, and TBDPSCl was purposefully developed in response to this demand.
First Synthesis and Report (1975)
In 1975, Stephen Hanessian and P. Lavallée from the Université de Montréal, Canada, published a pioneering paper in the Canadian Journal of Chemistry, reporting for the first time the synthesis of TBDPSCl and its application as a hydroxyl protecting group. Using diphenyldichlorosilane as the starting material, they efficiently prepared TBDPSCl via a low-temperature reaction with tert-butyllithium in an inert solvent, and systematically verified its protective performance. The study clearly demonstrated that TBDPSCl retained the general advantages of silyl ether protecting groups, while exhibiting stronger acid resistance and higher selectivity for primary hydroxyl groups, making it significantly superior to TBDMSCl.
Technological Breakthrough and Establishment of Position
The work of the Hanessian team not only accomplished the first synthesis of TBDPSCl but also established its core value through comparative experiments: under acidic hydrolysis conditions, TBDPS ethers are far more stable than TBDPS ethers; their protective selectivity for primary hydroxyl groups is markedly higher than that for secondary hydroxyl groups, making them suitable for the precise modification of polyhydroxy molecules. This breakthrough quickly established TBDPSCl as the preferred protecting reagent for the synthesis of nucleosides, oligonucleotides, and complex carbohydrates, driving the refined development of organic synthesis strategies.
Subsequent Development and Industrialization
After 1975, the synthetic process of TBDPSCl was continuously optimized, gradually scaling up from laboratory-scale trials to industrial production. For instance, the safer tert-butyl Grignard reagent was adopted to replace tert-butyllithium, improving the feasibility and safety of large-scale preparation. To this day, TBDPSCl remains an indispensable standard reagent in the fields of organic synthesis and medicinal chemistry, and its discovery history has become a typical example of the translational application of organosilicon reagents from basic research to practical utilization.
Safety and Operating Precautions
Safety Information Overview
Tert-Butylchlorodiphenylsilane (CAS No. 58479-61-1) is a corrosive and irritating chemical substance belonging to Hazardous Rank 8 (Corrosive substances), Packing Group II. Its Hazardous Goods symbols are C (Corrosive) and Xi (Irritant), and its Hazardous Goods Transportation Number is UN 2987 8/PG 2. It is a strong irritant to the skin, eyes and respiratory tract, and may even cause severe burns. The substance is a strong irritant to the skin, eyes and respiratory tract, and may even cause serious burns.
Operating Precautions
Operating Environment Requirements
Ventilation Conditions: All operations must be carried out in a fume hood or a place with a local exhaust system to avoid inhaling vapors or dust.
Equipment Requirements: Use explosion-proof ventilation system and equipment, and the reaction vessel should be grounded to prevent static buildup.
Ignition source control: Keep away from fire and heat source, smoking is strictly prohibited in the workplace, and avoid the use of open flame or tools that may generate sparks.
Personal protective measures
Protective equipment: Protective gloves (e.g. rubber oil-resistant gloves), protective clothing, eye protection and gas mask must be worn during operation to prevent skin, eye and respiratory tract contact.
Practice: Avoid direct contact with reagents and prohibit eating, drinking or smoking in the workplace. Thorough washing of skin and clothing is required after operation to prevent health hazards from residues.
Operation Procedure Specifications
Reaction Control: When initiating the reaction, it is necessary to slowly heat and strictly control the temperature (50-75℃) to avoid violent reaction leading to equipment damage or safety accidents. If the reaction is too violent, reduce the temperature and stop heating immediately.
Dropping operation: The dropping of chloropropene and diphenyl dichlorosilane should be carried out slowly to prevent the local concentration from being too high and causing side reactions or danger.
Post-processing safety: After the reaction, when adding toluene and stirring and filtering, protective equipment should be worn to prevent the solid salt from splashing or contacting the skin. Distillation and decompression distillation process need to be carried out in a well-ventilated environment to avoid steam accumulation.
Storage precautions
Storage conditions
Temperature control: stored in a cool, ventilated warehouse, the warehouse temperature should not exceed 37 ℃, to avoid high temperatures leading to reagent decomposition or volatilization.
Container requirements: Use corrosion-resistant glass bottles or metal containers for sealed storage, containers need to be locked and placed in a place inaccessible to children.
Segregation measures: Store separately from oxidizers and edible chemicals, avoid mixed storage to prevent chemical reaction leading to danger.
Environmental safety
Lightning and anti-static: the warehouse must be installed with lightning protection equipment, and the exhaust system must be equipped with a grounding device for electrostatic conductivity to prevent static electricity from causing fire or explosion.
Lighting and ventilation: Adopt explosion-proof lighting and ventilation equipment, prohibit the use of spark-producing equipment and tools to ensure the safety of the storage environment.
Emergency measures
Leakage emergency treatment
Personnel protection: Emergency personnel need to wear air-carrying respirators and anti-static clothing, and are prohibited from contacting or crossing the leakage.Leakage control: Cut off the source of leakage as far as possible, absorb the leakage with sand, activated charcoal or other inert materials, and transfer it to a safe place.
It is forbidden to flush the leakage into the sewer to prevent pollution of the environment.
Large area leakage: construct a dike or dig a pit to shelter, cover with foam to inhibit evaporation, and use explosion-proof pumps to transfer to tanker trucks or special collectors for recycling and treatment.
First aid measures
Skin contact: immediately remove contaminated clothing, flush skin with plenty of water for at least 15 minutes, and seek medical assistance.
EYE CONTACT: Separate eyelids, flush with running water or saline for at least 15 minutes, and call an emergency center immediately.
Inhalation: Move the patient to fresh air and keep him/her breathing; if breathing stops, perform artificial respiration and call the emergency center immediately.
Treatment of accidental ingestion: Rinse mouth and prohibit vomiting, call emergency center or doctor immediately.
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