Dichlorophenylborane
Dichlorophenylborane (CAS: 873-51-8), with the molecular formula C6H5BCl2 and a molecular weight of 158.82 g/mol, is a reactive organoboron compound. It serves as a valuable reagent in various organic syntheses, particularly as a catalyst or intermediate. Its applications span stereoselective reactions, cycloadditions, and the synthesis of complex organic molecules, making it a key component in advanced chemical research and development.
- IUPAC
- NSC 93889,Phenylboron dichloride,Phenyldichloroborane
Catalysis in Organic Synthesis
Dichlorophenylborane acts as a catalyst in diverse organic transformations. It is employed in enantioselective syntheses, such as vinylogous Mukaiyama aldol reactions and Diels-Alder cycloadditions, facilitating the creation of complex chiral molecules.
Synthesis of Lactimidomycin
This compound is utilized as a catalyst in the synthesis of antiproliferative macrolides, including lactimidomycin, a known cell migration inhibitor. This highlights its role in the development of potentially therapeutic agents.
Stereoselective Reactions
It promotes stereoselective alkylative ring opening of cyclic anhydrides and asymmetric acetate aldol reactions. These applications are crucial for building specific stereochemical configurations in organic molecules.
Cross-Metathesis and Aldehyde Reactions
Dichlorophenylborane facilitates cross-metathesis reactions of amino derivatives with olefins. It also participates in reactions involving aryl aldehydes with styrene and (E)-β-methylstyrene.
| Molecular weight | 158.82 |
|---|---|
| Empirical formula | C6H5BCl2 |
| Assay | 97% |
| Boiling point | 66 °C/11 mmHg(lit.) |
| Density | 1.224 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.545(lit.) |
| Application | Catalyst for: • Antiproliferative macrolide and cell migration inhibitor lactimidomycin1• Enantioselective synthesis of polyketide segments using vinylogous Mukaiyama aldol reactions2• Enantioselective Diels-Alder cycloadditions after its reaction with allo-threonine derivatives3• Stereoselective alkylative ring opening of cyclic anhydrides4• Cross-metathesis reaction of amino derivatives with olefins5• Asymmetric acetate aldol reactions6• The reaction of aryl aldehydes with styrene and (E)-β-methylstyrene7 |
Hazard statements
- H225Highly flammable liquid and vapour
- H314Causes severe skin burns and eye damage
Precautionary statements
- P210Keep away from heat, sparks and open flames. No smoking
- P280Wear protective gloves, clothing and eye/face protection
- P305IF IN EYES
- P310Immediately call a POISON CENTER or doctor
| Protective equipment | Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 14 °C / 57.2 °F |
| Transport (UN / ADR) | UN 2924 8(3) / PGII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | F,C |
| Risk statements (R) | 11-34-37 |
| Safety statements (S) | 16-26-36/37/39-45 |
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 Dichlorophenylborane used for?
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Dichlorophenylborane (CAS: 873-51-8) is primarily used as a catalyst in various organic synthesis applications, including enantioselective reactions like aldol reactions, Diels-Alder cycloadditions, and the synthesis of complex molecules such as lactimidomycin.
What are the CAS number and formula for Dichlorophenylborane?
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The CAS number for Dichlorophenylborane is 873-51-8, and its molecular formula is C6H5BCl2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Dichlorophenylborane with an assay of 97%. This product is not represented as USP, BP, or EP grade.
How should Dichlorophenylborane be handled safely?
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Dichlorophenylborane is a Danger hazard (H225-H314), flammable, and causes severe skin burns and eye damage. Handle with appropriate personal protective equipment, including a full-face respirator, gloves, and goggles, in a well-ventilated area. Ensure protection against ignition sources.
How is Dichlorophenylborane packed and shipped?
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Dichlorophenylborane is shipped as UN 2924, Hazard Class 8(3), Packing Group II. Specific packing details are available upon request, adhering to all international shipping regulations for hazardous materials.
How can I request a sample or quote for Dichlorophenylborane?
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To request a sample or a quote for Dichlorophenylborane, please contact our sales team via the website or directly by phone. Please specify the quantity required.
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