4-Bromotetrahydropyran
4-Bromotetrahydropyran (CAS: 25637-16-5; Formula: C5H9BrO; MW: 165.03) is a versatile heterocyclic building block. This tetrahydropyran derivative serves as a key reactant in various organic synthesis pathways. Its applications include nickel-catalyzed coupling reactions, preparation of biologically active compounds, and the synthesis of complex organic molecules.
- IUPAC
- 4-Bromooxacyclohexane,4-Bromotetrahydro-2H-pyran
- Synonyms
- 4-Bromooxacyclohexane4-Bromotetrahydro-2H-pyran
Nickel-Catalyzed Coupling Reactions
4-Bromotetrahydropyran is utilised as a reactant in nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents and for the preparation of aliphatic hydrocarbons via Suzuki cross-coupling with alkylboranes.
Melanocortin-4 Receptor Agonist Preparation
This compound is employed in the preparation of selective small-molecule melanocortin-4 receptor agonists, which have shown efficacy in pilot studies for treating sexual dysfunction in humans.
Antibacterial Agent Synthesis
It is a precursor in the preparation of anthranilic acids, which have demonstrated antibacterial properties and human serum albumin binding affinity.
Antioxidant Synthesis
4-Bromotetrahydropyran can be used in Grignard reactions with specific benzaldehyde derivatives to prepare antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols.
Gephyrotoxin Synthesis
This chemical intermediate is a reactant in the synthesis of gephyrotoxin through the Schmidt reaction.
| Molecular weight | 165.03 |
|---|---|
| Empirical formula | C5H9BrO |
| Density | 1.467 g/cm3 at 25 °C |
| Refractive index | n20/D 1.497 |
| Application | Reactant for:• Nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagents1• Preparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans2• Preparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranes3• Preparation of anthranilic acids as antibacterial agents with human serum albumin binding affinity4• Preparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivatives5• Synthesis of gephyrotoxin via the Schmidt reaction6 |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Flash point | 71 °C / 159.8 °F |
|---|---|
| Transport (UN / ADR) | NA 1993 / PGIII |
| Water hazard class (WGK, DE) | 2 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36/37/39 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 4-Bromotetrahydropyran used for?
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4-Bromotetrahydropyran is a versatile building block used in organic synthesis, including nickel-catalyzed coupling reactions, preparation of biologically active compounds like melanocortin-4 receptor agonists and antibacterial agents, and synthesis of complex molecules such as gephyrotoxin.
What are the CAS number and formula for 4-Bromotetrahydropyran?
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The CAS number is 25637-16-5, and the empirical formula is C5H9BrO.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies 4-Bromotetrahydropyran with a purity of 97%. While it is suitable for research and chemical synthesis, TSS does not represent it as USP, BP, or EP grade.
How should 4-Bromotetrahydropyran be handled safely?
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4-Bromotetrahydropyran is a warning substance that causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Handle with appropriate personal protective equipment, ensuring good ventilation, and avoid breathing dust/fume/gas/mist/vapours/spray. In case of contact with eyes, rinse cautiously with water for several minutes, removing contact lenses if present and easy to do. Continue rinsing.
How is 4-Bromotetrahydropyran packed and shipped?
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4-Bromotetrahydropyran is typically packed in compliance with transport regulations and can be exported globally by Tech Serve Solutions.
How can I request a sample or quote for 4-Bromotetrahydropyran?
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To request a sample or quote, please contact the Tech Serve Solutions sales team via our website or direct enquiry channels.
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