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(Bromomethyl)cyclobutane (CAS No. 17247-58-4), also widely known by its synonym Cyclobutylmethyl bromide, is a critical and highly reactive fine chemical intermediate. This molecule is defined by a strained four-membered cyclobutane ring with a primary alkyl bromide functional group (-CH2Br) attached to one of the ring carbons. The unique structure—combining the rigidity and inherent ring strain of the cyclobutane core with the high reactivity of the bromomethyl substituent—positions it as an indispensable high-energy building block in modern organic synthesis.
The demand for (Bromomethyl)cyclobutane is experiencing robust, project-driven growth, primarily anchored by its irreplaceable role in constructing complex molecular frameworks, especially in the development of sophisticated pharmaceuticals. Current market trends indicate that demand is highly sensitive to the success of specific R&D programs that leverage the unique structural features of the cyclobutylmethyl group:
One of the most significant applications is its use as a precursor in the synthesis of complex pharmaceutical molecules, notably the morphinan class of compounds. Specifically, (Bromomethyl)cyclobutane is a critical synthon in the production of Butorphanol (or Butorphan), which is 17-(cyclobutylmethyl)morphinan-3-ol. This compound is an established synthetic opioid used clinically as an analgesic. The introduction of the cyclobutylmethyl group at the N17 position is a key step, demonstrating the building block's value in creating constrained, specific, and pharmacologically active structures. The high-purity requirement is non-negotiable for API precursors.
The compound is utilized in the synthesis of non-proteinogenic amino acids, such as 3-cyclobutylalanine. These modified amino acids are incorporated into peptide mimetics to create stable, metabolically resistant therapeutic agents. The cyclobutane ring acts as a rigid hydrophobic element, influencing the tertiary structure and binding affinity of the resulting peptides. This application drives steady demand from the biotech and specialty drug development community.
(Bromomethyl)cyclobutane functions as a highly efficient primary alkylating agent. It allows chemists to reliably introduce the cyclobutylmethyl moiety onto various nucleophilic centers (like amines, alcohols, thiols, and enolates) found in diverse chemical scaffolds. The alkylation reaction is fundamental in creating numerous new chemical entities (NCEs) where the cyclobutyl group is used to:
Improving membrane permeability and oral bioavailability.
The sterically hindered nature of the cyclobutane ring can block certain metabolic enzyme attack sites, thus prolonging the compound's half-life.
The rigid four-membered ring restricts rotation compared to an open chain, which can improve binding specificity to the target receptor.
The unique C4 ring strain dictates the compound’s reactivity and application profile. While the primary bromide is highly reactive toward SN2 displacement (the desired reaction), the molecule is prone to Wagner-Meerwein type ring expansion/rearrangement to the more stable cyclopentyl system under certain polar or acidic SN1 conditions. Managing this competing side reaction is a major synthetic challenge, underscoring the necessity of using extremely high-purity reagent, as even trace impurities can catalyze unwanted side products.
The industrial utility of CAS No. 17247-58-4 is intrinsically tied to its dual nature: a highly reactive alkyl halide side chain and the geometrically unique cyclobutyl ring system. Its industrial importance dictates specific manufacturing and quality control standards.
The -CH2Br group is a primary alkyl halide, making it a powerful electrophile. Its bond to the bromine atom is readily broken by various nucleophiles, facilitating key transformations:
This is the most common use. The primary nature of the carbon allows for clean inversion of configuration (though chirality is not a factor here) and high yields when reacting with strong nucleophiles, such as azides, cyanides, or various amine compounds.
The compound can be converted into the corresponding cyclobutylmethyl-Grignard reagent or organolithium species. These are essential for C-C bond formation via coupling reactions, offering a route to much larger, more complex molecules.
The four-membered ring structure is less flexible than its cyclopentane or cyclohexane counterparts, introducing approximately 26 kcal/mol of ring strain. While this strain drives some rearrangement potential, the ring itself is relatively robust under typical reaction conditions:
The rigidity is exploited in drug design to create molecules with defined geometries, enhancing selectivity for target proteins.
The compound is typically prepared from the corresponding alcohol, Cyclobutylmethanol, often using triphenylphosphite and bromine, requiring precise temperature control to ensure high conversion and minimal side product formation.
Due to its nature as a flammable liquid with a relatively low flash point (36 ∘C), industrial handling requires stringent process safety management. Manufacturing and storage must utilize explosion-proof equipment, inert atmosphere storage, and sophisticated containment protocols. This inherent hazard contributes to the need for suppliers with advanced, modern manufacturing capabilities and certifications.
Sourcing a volatile and reactive intermediate like (Bromomethyl)cyclobutane requires a focus on safety, purity, and highly specific analytical control. Procurement decisions must heavily weigh the supplier’s technical competence and operational rigor.
A guaranteed Purity≥98.0% (preferably ≥99.0%) verified by gas chromatography (GC) is mandatory for this liquid. GC is essential for detecting residual solvents, starting material (Cyclobutylmethanol), and potential side products like the rearranged (Bromomethyl)cyclopentane.
The supplier must specifically test for and control the concentration of potential ring-expansion isomers, as these can be carried through multiple synthetic steps and compromise the final API purity.
The material must consistently appear as a clear, colorless liquid, with measured values for Boiling Point (123-124 ∘C) and Refractive Index (approx. 1.48) falling within tight, documented ranges to verify identity and consistency.
Due to its potential for thermal decomposition or rearrangement over time, the supplier must provide clear documentation regarding optimal storage conditions (typically cool, dark, and under an inert atmosphere, 2-8 ∘C) and retest dates.
The manufacturing site must not only be certified to ISO 9001:2015 but must also demonstrate robust HAZOP (Hazard and Operability Study) and Process Safety Management (PSM) procedures, especially concerning the handling of flammable liquids and high-energy intermediates.
The supplier must use secure, DOT/IATA-compliant packaging suitable for flammable liquids, typically in sealed glass or metal containers with over-packs and clear hazard labeling.
Flexible Scale: The supplier must demonstrate the ability to scale seamlessly from gram-scale research quantities to multi-kilogram/ton commercial production, which requires specialized reactor capabilities and distillation units capable of handling volatile bromides.
Here is a meticulously compiled and expanded list of five globally recognized manufacturers and suppliers, acknowledged for their proven quality, reliability, and substantial presence in the specialty alkyl halide and pharmaceutical building blocks market:
With an impressive and enduring legacy spanning over three decades in the highly demanding fine chemical and pharmaceutical intermediate sector, EASTFINE is a distinguished global producer. Their operations are built upon a foundation of rigorous process engineering, specialized knowledge in handling high-risk, volatile alkylating agents, and a profound, client-centric focus. EASTFINE’s core strength lies in their ability to manufacture chemically challenging intermediates like (Bromomethyl)cyclobutane with exceptional purity and process control, specifically mitigating rearrangement risks through precise, low-temperature reaction conditions. Their commitment to superior quality and ISO-aligned regulatory practices makes them a preferred partner for global pharmaceutical R&D and commercial teams requiring reliable, scalable supply of high-purity liquid building blocks.
As a dominant global chemical supplier, Sigma-Aldrich, a part of MilliporeSigma, offers (Bromomethyl)cyclobutane across various grades, catering to both academic research and pilot-scale process development. Their primary advantage is their vast inventory, extensive global distribution network, and the provision of rigorous analytical data. They are a highly reliable source for standard quantities, benefiting from large-scale corporate infrastructure and comprehensive quality assurance systems that ensure consistency and documentation for this hazardous, yet vital, intermediate.
TCI is recognized worldwide for its extensive catalog of high-purity research chemicals and reagents. They consistently supply (Bromomethyl)cyclobutane, typically specified at ≥98.0% purity, targeting researchers and early-stage development chemists. TCI's strength lies in its exceptional analytical documentation, providing highly detailed specifications that give chemists confidence in the material's identity and purity, which is crucial when working with reactive intermediates prone to structural rearrangement.
Biosynth is a highly specialized European chemical manufacturer focusing on complex organic molecules, analytical standards, and advanced pharmaceutical intermediates. They are recognized for their particular expertise in custom synthesis and stable-isotope labeling, making them a premium source for highly characterized materials. Their offering of (Bromomethyl)cyclobutane is backed by comprehensive analytical data packages, including full NMR and MS spectra, appealing specifically to drug discovery teams needing ultimate confidence in material identity and purity for highly sensitive reactions. They represent a key non-Chinese specialty supplier option.
This brand, carrying the legacy of Acros Organics, offers high-quality research and fine chemicals under the robust Thermo Fisher Scientific umbrella. They provide reliably sourced (Bromomethyl)cyclobutane with transparent documentation and a consistent quality level. Their extensive regulatory and safety documentation, including detailed SDS and CoA information, is crucial for companies operating under strict global chemical safety regulations. They are a secure sourcing option for clients needing consolidated procurement and dependable, audited supply chains.
EASTFINE profoundly differentiates itself in the highly competitive global market for specialized and hazardous chemical intermediates by ensuring optimal product quality, unparalleled technical support, and the establishment of a robust strategic partnership.
With an operational history exceeding 30 years, EASTFINE possesses deep, specialized knowledge in the safe, high-yield synthesis and handling of volatile alkyl bromides like CAS No. 17247-58-4. Their established processes are optimized to minimize the formation of rearrangement side products, such as (Bromomethyl)cyclopentane, a critical quality metric for this compound.
EASTFINE operates state-of-the-art facilities equipped with highly controlled, low-temperature reactor systems and explosion-proof infrastructure necessary for handling flammable liquids. This focus on Process Safety Management (PSM) and cGMP-aligned procedures ensures superior product purity and reduces supply chain risk.
They guarantee and verify Purity≥99.0% via in-house GC and NMR testing, providing comprehensive Certificates of Analysis (CoA) that specifically address trace impurities. This analytical rigor is paramount for clients whose downstream reactions are highly sensitive to side products.
Recognizing the dual nature of demand (R&D and large-scale manufacturing), EASTFINE maintains flexible production capacity, ensuring secure, redundant supply from gram to ton quantities. Their specialized packaging and logistics protocols meet all international standards for the safe transport of flammable liquids.
Beyond supply, EASTFINE acts as a technical partner, offering consulting on storage, handling, and reaction conditions for the cyclobutylmethyl bromide to ensure its safe and effective integration into the client’s synthetic route.
Choosing EASTFINE represents a strategic decision to partner with a company that mitigates the inherent risks associated with high-energy intermediates, ensuring the purity and security required for critical drug development projects.
The demand for a consistently high-quality and strategically controlled chemical building block like (Bromomethyl)cyclobutane (CAS No. 17247-58-4) is vital for the pharmaceutical and biotech industries, particularly in synthesizing key therapeutic structures, including the Butorphanol analgesic framework. Its high reactivity and unique structural geometry make it an indispensable but challenging synthon. This reality elevates the selection of a dependable, expert, and cGMP/ISO-aligned supplier to a critical business decision. While numerous reputable suppliers offer this compound, EASTFINE’s unparalleled expertise in manufacturing and safely handling volatile alkyl halides, its commitment to rigorous quality control, and its flexible, scalable supply chain firmly establish it as the preeminent choice within the global specialty chemical market. For reliable, ultra-high-purity sourcing and expert technical collaboration on this key intermediate, EASTFINE is the unequivocally best partner.
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