2-Bromobicyclo[2.2.1]heptane: Properties, Uses & FAQs
2-Bromobicyclo[2.2.1]heptane: Properties, Uses & FAQs
2-Bromobicyclo[2.2.1]heptane is a strained bicyclic alkyl bromide, also known as 2-bromonorbornane, widely used as a synthetic intermediate in organic chemistry research due to its distinctive bridged ring geometry and reactivity.
- IUPAC Name
- 2-Bromobicyclo[2.2.1]heptane
- Common Synonym
- 2-Bromonorbornane
- Molecular Formula
- C₇H₁₁Br
- Molecular Weight
- 175.07 g/mol
- Ring System
- Bridged bicyclic (norbornane skeleton)
- Aladdin SKU
- B588611
- Primary Application
- Synthetic intermediate in organic and medicinal chemistry
Chemical Identity and Structure
2-Bromobicyclo[2.2.1]heptane, commonly referred to as 2-bromonorbornane, is an organobromine compound built upon the norbornane (bicyclo[2.2.1]heptane) skeleton. The compound bears a bromine substituent at the C-2 position of the bridged bicyclic framework, giving rise to a chiral center and the possibility of both exo and endo stereoisomers.
The norbornane core is characterized by significant ring strain arising from the bridged bicyclic architecture, which influences the compound's conformational rigidity and its reactivity in downstream transformations. The molecular formula is C₇H₁₁Br, with a molecular weight of approximately 175.07 g/mol.
Aladdin Scientific supplies this compound under SKU B588611. Researchers should consult the product specification sheet for confirmed purity, stereochemical composition, and physical constants prior to use.
Reactivity and Synthetic Applications
As a secondary alkyl bromide on a rigid bicyclic scaffold, 2-Bromobicyclo[2.2.1]heptane exhibits reactivity that is strongly governed by steric and stereoelectronic factors associated with the norbornane framework. The bridged ring system enforces strict geometric constraints that make classical SN2 displacement at C-2 highly disfavored, while solvolysis and elimination pathways may proceed with characteristic stereoselectivity.
Key synthetic uses include:
- Solvolysis studies: The compound is a classical substrate for investigating non-classical carbocation intermediates and neighboring-group participation in physical organic chemistry.
- Grignard or organolithium formation: Under appropriate conditions, the C–Br bond can be activated to generate organomagnesium or organolithium species for further carbon–carbon bond-forming reactions.
- Radical reactions: Alkyl bromides of this type can participate in radical chain processes, useful in constructing complex polycyclic frameworks.
- Cross-coupling precursors: May serve as a starting material for transition-metal-catalyzed coupling when suitably functionalized.
Stereochemical outcome in any reaction should be carefully evaluated given the exo/endo isomeric nature of the starting material.
Handling, Storage, and Safety Considerations
As with all organobromine compounds, appropriate laboratory safety practices must be observed when working with 2-Bromobicyclo[2.2.1]heptane. General precautions include:
- Personal protective equipment (PPE): Wear chemical-resistant gloves, safety glasses or goggles, and a laboratory coat. Work in a well-ventilated fume hood.
- Storage: Store in a tightly sealed container in a cool, dry, well-ventilated location, away from moisture, heat sources, and incompatible materials such as strong bases and reducing agents. Specific storage temperature recommendations should be confirmed on the Aladdin product specification sheet for SKU B588611.
- Disposal: Dispose of waste in accordance with local, national, and institutional regulations for halogenated organic compounds.
Note: Precise hazard classifications (GHS pictograms, H-statements, P-statements) and physical property data (boiling point, density, flash point) should be obtained directly from the current Safety Data Sheet (SDS) provided by Aladdin Scientific for SKU B588611, as these values are subject to revision and depend on purity and isomeric form.
Ordering and Product Specifications
2-Bromobicyclo[2.2.1]heptane is available from Aladdin Scientific under SKU B588611. When placing an order or evaluating suitability for your research, the following steps are recommended:
- Confirm specifications: Download the current Certificate of Analysis (CoA) and Safety Data Sheet (SDS) from the Aladdin Scientific website to verify purity grade, stereoisomeric ratio (exo/endo), and physical data.
- Select quantity: Contact Aladdin Scientific sales or procurement teams for available pack sizes and bulk pricing options.
- Check availability: Stock levels and lead times vary; confirm availability through the Aladdin Scientific online catalog or customer service.
- Regulatory compliance: Ensure that import/export regulations applicable to organobromine compounds in your jurisdiction are met prior to ordering.
For technical inquiries regarding this product, contact Aladdin Scientific technical support with reference to SKU B588611.
Frequently asked questions
What is 2-Bromobicyclo[2.2.1]heptane and what is its common name?
2-Bromobicyclo[2.2.1]heptane is an organobromine compound consisting of a norbornane (bicyclo[2.2.1]heptane) skeleton with a bromine substituent at the C-2 position. It is commonly known as 2-bromonorbornane and has the molecular formula C₇H₁₁Br (MW ≈ 175.07 g/mol). The compound can exist as exo and endo stereoisomers due to the geometry of the bridged bicyclic ring system.
What are the main synthetic applications of 2-Bromobicyclo[2.2.1]heptane in organic chemistry?
This compound is primarily used as a synthetic intermediate and a classical substrate for studying non-classical carbocation chemistry and solvolysis reactions due to the ring strain and rigid geometry of the norbornane framework. It can also be converted to organomagnesium or organolithium species for carbon–carbon bond-forming reactions, and may participate in radical reactions or serve as a precursor for transition-metal-catalyzed cross-coupling processes.
Does 2-Bromobicyclo[2.2.1]heptane readily undergo SN2 substitution?
No. The bridged bicyclic norbornane skeleton imposes severe steric and geometric constraints at C-2, making classical backside SN2 attack by a nucleophile highly disfavored. Reactions at this center are more likely to proceed via solvolysis (SN1-type pathways), elimination, or radical mechanisms rather than direct bimolecular substitution.
How should 2-Bromobicyclo[2.2.1]heptane be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from moisture, heat, and incompatible substances such as strong bases and reducing agents. Researchers should consult the current Safety Data Sheet and Certificate of Analysis for SKU B588611 from Aladdin Scientific for specific recommended storage temperatures and conditions.
How can I order 2-Bromobicyclo[2.2.1]heptane from Aladdin Scientific?
2-Bromobicyclo[2.2.1]heptane is available from Aladdin Scientific under SKU B588611. You can place an order through the Aladdin Scientific online catalog or contact the sales and customer service team directly. It is recommended to download the CoA and SDS prior to ordering to confirm that the purity grade and stereoisomeric composition meet your experimental requirements.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for norbornyl carbocation and bridged bicyclic chemistry.)
- Aladdin Scientific. Product page and Safety Data Sheet for 2-Bromobicyclo[2.2.1]heptane, SKU B588611.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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