1-BroMo-4-(t-butyldiMethylsilyloxy)butane

1-Bromo-4-(t-butyldimethylsilyloxy)butane is a bifunctional C4 building block that finds extensive application as a key synthetic intermediate in medicinal chemistry and pharmaceutical process development. The primary alkyl bromide in 1-Bromo-4-(t-butyldimethylsilyloxy)butane serves as a versatile electrophilic handle for nucleophilic substitution reactions with amines, alkoxides, thiols, and stabilized carbanions, while also participating in metal-halogen exchange and cross-coupling transformations. In the rapidly evolving field of targeted protein degradation, 1-Bromo-4-(t-butyldimethylsilyloxy)butane has emerged as a frequently employed PROTAC (Proteolysis Targeting Chimera) linker building block, where its four-carbon spacing and orthogonal protecting group strategy facilitate the convergent assembly of heterobifunctional degrader molecules. The TBS protecting group of 1-Bromo-4-(t-butyldimethylsilyloxy)butane remains stable under a broad range of reaction conditions yet can be selectively removed under mild fluoride-mediated or acidic protocols to reveal 4-bromobutan-1-ol for further functional elaboration. The combination of predictable reactivity, commercial availability in high purity, and compatibility with diverse synthetic methodologies has established 1-Bromo-4-(t-butyldimethylsilyloxy)butane as an indispensable tool in the modern synthetic chemist‘s repertoire.

Product Parameters

Why Cosperpharm?

When your synthetic route or analytical method validation requires a high-purity, reliably sourced TBS-protected bromoalkane, Cosperpharm delivers 1-Bromo-4-(t-butyldimethylsilyloxy)butane with the documentation depth, supply consistency, and technical guidance that synthetic chemists and QC managers expect.

Dual-grade supply for diverse applications. Cosperpharm offers 1-Bromo-4-(t-butyldimethylsilyloxy)butane at two quality levels: a high-purity grade (≥97%) suitable as a building block in multi-step pharmaceutical syntheses and PROTAC linker assembly, and a standard grade (≥95%) suitable for general organic synthesis and method development. Both grades are accompanied by comprehensive characterization data.

Documentation aligned with your workflow. Every shipment of 1-Bromo-4-(t-butyldimethylsilyloxy)butane includes a Certificate of Analysis (COA) with batch-specific purity data (GC or HPLC), analytical traces, and residual solvent information. Our documentation is structured for direct integration into your synthetic records or regulatory submissions.

Seamless scale-up from bench to pilot. Cosperpharm bridges the gap between discovery and development. You can obtain small gram quantities of 1-Bromo-4-(t-butyldimethylsilyloxy)butane for route scouting and feasibility studies, and then seamlessly transition to kilogram-scale quantities for process validation without changing suppliers.

Technical guidance on handling and reactivity. Our application scientists possess deep knowledge of silyl protecting group chemistry and alkyl bromide reactivity. They can provide practical guidance on storage, handling, and compatibility of 1-Bromo-4-(t-butyldimethylsilyloxy)butane with common synthetic transformations—including nucleophilic substitution, metal-halogen exchange, and deprotection conditions.

Global logistics with predictable timelines. Cosperpharm maintains a robust global supply chain. Every shipment of 1-Bromo-4-(t-butyldimethylsilyloxy)butane is packed under controlled conditions and accompanied by comprehensive commercial invoices, packing lists, and certificates of origin to ensure smooth customs clearance worldwide.

Synthetic Route

The preparation of 1-Bromo-4-(t-butyldimethylsilyloxy)butane is typically accomplished via silyl protection of commercially available 4-bromo-1-butanol.

In a representative procedure, 4-bromo-1-butanol is treated with tert-butyldimethylsilyl chloride (TBSCl, 1.05–1.2 equivalents) in anhydrous dichloromethane or DMF at 0°C to room temperature in the presence of imidazole (2.0–2.5 equivalents) as a base and nucleophilic catalyst. The reaction proceeds via nucleophilic attack of the primary alcohol oxygen on the silicon center of TBSCl, displacing chloride and forming the silyl ether with concomitant precipitation of imidazole hydrochloride. After stirring for 12–24 hours, the reaction mixture is quenched with water, extracted with dichloromethane, and the organic layer is washed with brine, dried over anhydrous sodium sulfate or magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by vacuum distillation or silica gel column chromatography (typically eluting with hexanes or petroleum ether/ethyl acetate mixtures) to afford 1-Bromo-4-(t-butyldimethylsilyloxy)butane as a colorless to pale yellow liquid. Typical yields range from 85–95%, with purity exceeding 95% by GC analysis.

The reaction progress is conveniently monitored by TLC (visualized with potassium permanganate or phosphomolybdic acid stain) and the product is characterized by ¹H and ¹³C NMR spectroscopy, with the diagnostic methylene protons adjacent to the bromine atom appearing as a triplet in the region of δ 3.40–3.45 ppm and the tert-butyl dimethylsilyl protons observed as singlets at δ 0.89 (9H, t-Bu) and 0.06 (6H, Si(CH₃)₂) in CDCl₃.

FAQ

Q1: How should 1-Bromo-4-(t-butyldimethylsilyloxy)butane be stored?

A: Store at 2–8°C in a tightly sealed container under an inert atmosphere of nitrogen or argon, protected from moisture. The alkyl bromide is susceptible to hydrolysis and nucleophilic displacement, and the silyl ether is susceptible to hydrolytic cleavage; therefore, proper anhydrous storage conditions are essential for maintaining product integrity.

Q2: What documentation is provided with each shipment?

A: Each shipment includes a Certificate of Analysis (COA) with purity data and analytical traces, a Material Safety Data Sheet (MSDS/SDS), and customs documentation for international delivery. DMF-ready documentation packages can be arranged for customers requiring process-related impurity reference data.

Contact Us

Looking to incorporate 1-Bromo-4-(t-butyldimethylsilyloxy)butane into your synthetic workflow or analytical method development? Reach out to Cosperpharm with your requirements, and our team will prepare a personalized quotation without delay.