(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide
(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide (CAS 59159-39-6) is a phosphonium salt with a molecular weight of 459.36. This compound is a valuable reagent in organic synthesis, primarily utilized in Wittig reactions and related olefination processes for carbon-carbon bond formation. It serves as a key building block in the stereoselective synthesis of various organic molecules, including esters and complex intermediates.
- IUPAC
- NSC 82468
Wittig Reaction Reagent
Serves as a key ylide precursor in the Wittig reaction for the synthesis of alkenes. It is particularly useful in Wittig methylenation reactions.
Preparation of α,β-Unsaturated Esters
Enables the stereoselective preparation of α-fluoro-α,β-unsaturated esters through deprotonation, fluorination, and subsequent stereoselective Wittig olefination with aldehydes.
Intermediate in Complex Synthesis
Acts as a reactant in rhodium-catalyzed asymmetric hydrogenation and is used in the preparation of specific diacetic acid esters via aza-Michael addition reactions.
C-C Bond Formation
Facilitates carbon-carbon bond formation, making it a versatile tool in synthetic organic chemistry for building molecular frameworks.
| Molecular weight | 459.36 |
|---|---|
| Linear formula | (CH3)3CO2CCH2P(C6H5)3Br |
| Assay | 98% |
| Application | Reactant for:• Rhodium-catalyzed asymmetric hydrogenation reactions1• Wittig reaction2• Wittig methylenation3• Preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via double aza-Michael addition reaction4• Stereoselective preparation of of α-fluoro-α,β-unsaturated esters via deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes5• Wittig chain extension reactions6 |
| Melting point | 178 °C (dec.)(lit.) |
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
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-37/39 |
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 (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide used for?
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(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide is primarily used as a reactant in Wittig reactions for alkene synthesis and in stereoselective preparation of various organic esters and intermediates.
What is the CAS number and molecular formula for this compound?
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The CAS number is 59159-39-6 and the linear molecular formula is (CH3)3CO2CCH2P(C6H5)3Br.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide with an assay of 98%. We do not represent this product as USP, BP, or EP grade.
How should (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide be handled?
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This compound is classified as a Warning with hazards H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Recommended personal protective equipment includes a dust mask (type N95 US), eyeshields, and gloves. Handle in a well-ventilated area.
Is this compound available for export?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, including (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide.
How can I request a sample or quote?
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Please contact our sales team via the website or direct email to request a sample or a quotation for (tert-Butoxycarbonylmethyl)triphenylphosphonium bromide.
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