Production Method 1

15054-86-1

86864-60-0

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Toluene
2.1 Reagents: Imidazole Solvents: Dichloromethane

Reference

Acid-Catalyzed Intramolecular Ring-Opening Reactions of Cyclopropanated Oxabenzonorbornadienes with Carboxylic Acid Nucleophiles

Ho, Angel; et al, Synthesis, 2022, 54(5), 1422-1430

(2-Bromoethoxy)-tert-butyldimethylsilane Raw materials

• Ethylene Glycol-d6

(2-Bromoethoxy)-tert-butyldimethylsilane Preparation Products

• (2-Bromoethoxy)-tert-butyldimethylsilane (86864-60-0)

• 1. Empowering microfluidics by micro-3D printing and solution-based mineral coating?
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  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 3. Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid
  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 4. Evolution and characterization of a benzylguanine-binding RNA aptamer?
  J. Xu,T. J. Carrocci,A. A. Hoskins Chem. Commun., 2016,52, 549-552
• 5. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651

• Solvents and Organic Chemicals Organic Compounds Organometallic compounds Organometalloid compounds Organosilicon compounds Organoheterosilanes
• Other Chemical Reagents Organic Metal Reagents
• Catalysts and Inorganic Chemicals Inorganic Compounds Oxides

Comprehensive Guide to (2-Bromoethoxy)-tert-butyldimethylsilane (CAS No. 86864-60-0): Properties, Applications, and Industry Insights

(2-Bromoethoxy)-tert-butyldimethylsilane (CAS No. 86864-60-0) is a specialized organosilicon compound widely utilized in organic synthesis and pharmaceutical intermediates. This bromo-functionalized silane is particularly valued for its role as a protecting group reagent in complex molecular architectures. With the increasing demand for high-purity silane derivatives in drug development, this compound has gained significant attention from researchers and manufacturers alike.

The molecular structure of (2-Bromoethoxy)-tert-butyldimethylsilane combines a tert-butyldimethylsilyl (TBS) group with a bromoethoxy moiety, creating unique reactivity patterns. Recent studies highlight its importance in click chemistry applications and bioconjugation techniques, especially in the development of targeted drug delivery systems. The compound's hydrolytic stability and selective reactivity make it particularly useful in multi-step synthetic routes where precise control over functional group transformations is required.

In pharmaceutical applications, CAS 86864-60-0 serves as a crucial building block for nucleoside modifications and prodrug development. The bromoethoxy group enables efficient etherification reactions, while the TBS protecting group provides excellent stability under various reaction conditions. Current research trends show growing interest in using this compound for oligonucleotide synthesis and biomaterial functionalization, particularly in the development of RNA-based therapeutics and diagnostic probes.

The synthesis of (2-Bromoethoxy)-tert-butyldimethylsilane typically involves silane coupling reactions with careful control of stoichiometry and reaction conditions. Manufacturers emphasize the importance of ultra-high purity grades (≥98%) for critical applications, with advanced analytical techniques like GC-MS and NMR spectroscopy employed for quality verification. Recent innovations in continuous flow chemistry have improved the scalability and consistency of production for this valuable intermediate.

From a market perspective, the demand for TBS-protected bromo compounds like 86864-60-0 continues to rise, driven by expanding applications in biopharmaceuticals and advanced materials. Industry reports indicate particular growth in its use for PEGylation chemistry and surface modification of medical devices. The compound's compatibility with green chemistry principles and potential for atom-economical transformations make it attractive for sustainable chemical development initiatives.

Handling and storage recommendations for (2-Bromoethoxy)-tert-butyldimethylsilane emphasize protection from moisture and strong oxidizers. Standard laboratory practices include storage under inert atmosphere and use of appropriate personal protective equipment. The compound demonstrates excellent stability when properly stored, with typical shelf lives exceeding 24 months under recommended conditions.

Emerging applications for CAS 86864-60-0 include its use in nanomaterial functionalization and bioorthogonal chemistry. Researchers are exploring its potential in creating smart polymer systems and responsive drug carriers. The compound's versatility in surface modification reactions positions it as a valuable tool in the development of next-generation biomaterials and diagnostic platforms.

Quality specifications for commercial (2-Bromoethoxy)-tert-butyldimethylsilane typically include parameters such as purity level, water content, and heavy metal impurities. Leading suppliers provide comprehensive analytical certificates and material safety data, with custom synthesis options available for specialized research needs. The compound's consistent performance in asymmetric synthesis and chiral auxiliary applications has established its reputation as a reliable synthetic tool.

Recent patent literature reveals innovative uses of 86864-60-0 in bioconjugation strategies and drug-linker technologies. Its application in antibody-drug conjugates (ADCs) development showcases the compound's importance in modern targeted cancer therapies. The bromoethoxy functionality serves as an efficient handle for subsequent click chemistry modifications, enabling precise control over drug-loading ratios and release profiles.

From an environmental perspective, (2-Bromoethoxy)-tert-butyldimethylsilane demonstrates favorable characteristics for industrial scale applications. Its efficient utilization in atom-transfer radical polymerization (ATRP) systems contributes to reduced waste generation compared to traditional methods. The compound's compatibility with microwave-assisted synthesis further enhances its sustainability profile by enabling energy-efficient transformations.

Future research directions for CAS 86864-60-0 include exploration of its potential in biohybrid material synthesis and enzyme immobilization techniques. The compound's unique structural features offer opportunities for developing novel molecular scaffolds in medicinal chemistry and chemical biology. As synthetic methodologies continue to advance, (2-Bromoethoxy)-tert-butyldimethylsilane remains a versatile building block with expanding applications across multiple scientific disciplines.

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