Catechol Bis(trifluoromethanesulfonate): Properties & Applications
Catechol Bis(trifluoromethanesulfonate): Properties & Applications
Catechol Bis(trifluoromethanesulfonate) is a highly reactive difunctional aryl bistriflate reagent derived from catechol, widely employed in organic synthesis as an efficient electrophilic triflating agent and versatile precursor for transition-metal-catalyzed cross-coupling reactions.
- Chemical Name
- Catechol Bis(trifluoromethanesulfonate)
- CAS Number
- 43064-38-6
- Molecular Formula
- C8H4F6O6S2
- Molecular Weight
- 372.23 g/mol
- Functional Groups
- Two aryl trifluoromethanesulfonate (triflate) groups
- Primary Use
- Electrophilic triflating agent; cross-coupling substrate
- SKU
- C153863
Chemical Structure and Properties
Catechol Bis(trifluoromethanesulfonate) (CAS 43064-38-6) is the bis-triflate ester of catechol (1,2-dihydroxybenzene), in which both phenolic hydroxyl groups are converted to trifluoromethanesulfonate (triflate, –OTf) leaving groups. The resulting compound bears the molecular formula C8H4F6O6S2 and a molecular weight of approximately 372.23 g/mol.
Triflate groups are among the best known leaving groups in organic chemistry, owing to the extraordinary stability of the trifluoromethanesulfonate anion (pKa of triflic acid ≈ –14). This renders each C–OTf bond highly susceptible to nucleophilic attack and oxidative addition by transition metals. The two ortho-disposed triflate groups on the benzene ring create a difunctional electrophile capable of sequential or simultaneous reactivity, making this compound a compact and information-rich building block.
The compound is typically encountered as a white to off-white crystalline solid, sensitive to moisture and best stored under inert atmosphere at low temperature in accordance with standard handling practices for reactive triflate esters.
Synthetic Applications and Reactivity
The primary utility of Catechol Bis(trifluoromethanesulfonate) lies in its role as a difunctional electrophilic coupling partner in transition-metal-catalyzed reactions. Aryl triflates are well-established substrates for palladium-catalyzed cross-coupling reactions including Suzuki–Miyaura (with boronic acids), Negishi (with organozinc reagents), Kumada (with Grignard reagents), Sonogashira (with terminal alkynes), and Buchwald–Hartwig amination reactions. The bistriflate functionality enables the construction of complex, multiply substituted aromatic or heteroaromatic systems from a single, simple precursor.
Because the two triflate groups are located in ortho positions, the compound can serve as a precursor to ortho-functionalized biaryl and polycyclic aromatic systems. Selective mono-coupling under carefully controlled conditions can yield mono-substituted intermediates for further elaboration, or double-coupling reactions can produce symmetric or unsymmetric 1,2-disubstituted benzene derivatives.
Beyond cross-coupling, aryl triflates derived from catechol have been explored as precursors to aryl cations, arynes, and other reactive intermediates. The compound may also serve as a triflating transfer agent in certain reaction contexts, though its primary application remains as an electrophilic cross-coupling substrate.
Handling, Storage, and Safety Considerations
As with all reactive triflate esters, Catechol Bis(trifluoromethanesulfonate) requires careful handling. Triflate esters can react vigorously with water, amines, and other nucleophiles, generating triflic acid as a byproduct, which is a strong and corrosive acid. Researchers should work in a well-ventilated fume hood, wearing appropriate personal protective equipment including chemical-resistant gloves, eye protection, and a laboratory coat.
Storage should be under anhydrous, inert conditions (e.g., under argon or nitrogen) at reduced temperature (typically 2–8 °C or as specified on the product label) to preserve reagent integrity and prevent hydrolysis. Containers should be sealed tightly and checked for moisture ingress before use.
Waste disposal must comply with local regulations for halogenated organic compounds and strong acid-generating materials. Researchers are strongly advised to consult the product Safety Data Sheet (SDS) for complete hazard information, first-aid measures, and disposal guidance before working with this compound.
Ordering and Specifications
Catechol Bis(trifluoromethanesulfonate) is available from Aladdin Scientific under SKU C153863. Researchers should confirm purity grade, available pack sizes, and current pricing through the Aladdin Scientific product catalog or by contacting the technical sales team directly.
When specifying this reagent for procurement, it is advisable to indicate the required purity grade (e.g., ≥97% or as analytically confirmed by the supplier), desired quantity, and any special storage or shipping requirements. For large-scale orders or custom specifications, Aladdin Scientific's customer service team can assist with tailored solutions.
For questions related to product specifications, compatibility with specific reaction systems, or bulk availability, researchers are encouraged to contact Aladdin Scientific technical support for expert guidance.
Frequently asked questions
What reactions is Catechol Bis(trifluoromethanesulfonate) most commonly used in?
Catechol Bis(trifluoromethanesulfonate) is most commonly employed as a difunctional electrophilic substrate in palladium-catalyzed cross-coupling reactions, including Suzuki–Miyaura, Negishi, Sonogashira, and Buchwald–Hartwig reactions. Its two aryl triflate groups allow for sequential or double functionalization of the catechol aromatic scaffold.
How should Catechol Bis(trifluoromethanesulfonate) be stored to maintain stability?
The compound should be stored under anhydrous, inert atmosphere conditions (argon or nitrogen) at low temperature, typically 2–8 °C. Exposure to moisture should be avoided, as hydrolysis of the triflate groups can degrade the reagent and generate corrosive triflic acid. Always reseal containers promptly after use.
Can Catechol Bis(trifluoromethanesulfonate) undergo selective mono-coupling reactions?
Yes, selective mono-coupling is possible under carefully controlled reaction conditions, including judicious choice of catalyst loading, temperature, solvent, and stoichiometry of the coupling partner. This strategy allows access to mono-substituted intermediates bearing one intact triflate group for subsequent transformation. However, achieving high selectivity may require optimization and is substrate-dependent.
What safety precautions should be observed when handling this compound?
Researchers should handle Catechol Bis(trifluoromethanesulfonate) in a fume hood, wearing chemical-resistant gloves, eye protection, and a laboratory coat. The compound is moisture-sensitive and can generate triflic acid upon hydrolysis, which is highly corrosive. Consult the Safety Data Sheet (SDS) before use for complete hazard, first-aid, and disposal information.
References
- Handy, S. T. Triflates in Organic Synthesis. In Comprehensive Organic Transformations; Wiley-VCH, general reference on aryl triflates in cross-coupling chemistry.
- Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction. Organic Reactions 1997, 50, 1–652. (General reference for aryl triflate cross-coupling reactivity.)
- Aladdin Scientific Product Catalog. Catechol Bis(trifluoromethanesulfonate), SKU C153863.
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