6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester
CAS255050-65-8
Methyl 6-(trifluoromethanesulfonyloxy)-1-naphthoate (CAS 255050-65-8) is an aryl triflate building block prepared from methyl 6-hydroxy-1-naphthoate. The triflate at the 6-position is a reactive handle for palladium-catalysed cross-coupling, while the methyl ester at the 1-position can later be hydrolysed or converted to amides, giving access to 1,6-disubstituted naphthalenes. KingPharm supplies research and production quantities with a batch-specific certificate of analysis.
![Chemical structure of 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester](https://chemsigma.com/chemicalStructure/25/255050-65-8.png)
- CAS No.
- 255050-65-8
- Formula
- C13H9F3O5S
- Mol. weight
- 334.27 g/mol
- Appearance
- Off-white to Light-brown Powder
Product Description
Methyl 6-(trifluoromethanesulfonyloxy)-1-naphthoate (C13H9F3O5S, MW 334.27) is a naphthalene derivative carrying a methyl ester at C-1 and a trifluoromethanesulfonate (triflate) ester at C-6. It is obtained by triflation of methyl 6-hydroxy-1-naphthoate and is used as an intermediate in medicinal chemistry.
The triflate is a strong leaving group that undergoes oxidative addition to palladium(0), so the C-6 position can be coupled with aryl boronic acids (Suzuki-Miyaura), alkynes, amines or other partners. The ester at C-1 is left intact under typical coupling conditions and is available for later hydrolysis, amidation or reduction.
Compared with the corresponding aryl bromide, the triflate is made in one step from the readily available hydroxynaphthoate, and its reactivity in palladium-catalysed couplings is comparable. This lets chemists diversify the 6-position from a phenol precursor without a separate halogenation route.
For procurement, check HPLC purity, residual methyl 6-hydroxy-1-naphthoate (the hydrolysis product of the triflate), the corresponding free acid, residual solvents and water content. Identity is normally confirmed by 1H NMR, and 19F NMR is useful for confirming the triflate group.
Chemical Specifications
Identifiers
| CAS number | 255050-65-8 |
|---|---|
| Product name | 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester |
| Chinese name | 6-三氟甲磺酰氧基-1-萘甲酸甲酯 |
| IUPAC name | methyl 6-(trifluoromethylsulfonyloxy)naphthalene-1-carboxylate |
| Synonyms | 1-Naphthalenecarboxylic acid, 6-[[(trifluoromethyl)sulfonyl]oxy]-, methylester |
| Molecular formula | C13H9F3O5S |
| Molecular weight | 334.27 g/mol |
| PubChem CID | 22622428 |
| InChIKey | HYZIXTMJSDGSDH-UHFFFAOYSA-N |
| SMILES | COC(=O)C1=CC=CC2=C1C=CC(=C2)OS(=O)(=O)C(F)(F)F |
Physical and chemical properties
| Appearance | Off-white to Light-brown Powder |
|---|
Applications
KingPharm supplies this aryl triflate as an intermediate for the following uses:
Suzuki-Miyaura coupling
The C-6 triflate couples with aryl boronic acids under palladium catalysis to give 6-aryl-1-naphthoate esters.
Other palladium-catalysed couplings
The triflate also serves as the electrophile in Sonogashira, Buchwald-Hartwig and carbonylation reactions to introduce alkynyl, amino or carbonyl groups at C-6.
1,6-Disubstituted naphthalene scaffolds
After coupling at C-6, the C-1 ester is hydrolysed or amidated to build naphthalene-based candidates in drug discovery programmes.
Quality Documentation
The following documents can be provided for 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester to support technical evaluation and purchasing. Documents are issued for the specific grade and batch supplied.
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Certificate of Analysis (COA) Batch-specific test results against the specification.
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Product specification The release specification with test items, limits and methods.
Packaging, Storage & Transport
| Available pack sizes | 10 kg, 1 kg, 500 g, 100 g, 25 g |
|---|
Safety and transport
| Hazard Level | 固体普货 |
|---|
Read the current safety data sheet before handling. Packaging can be adapted to the order quantity and destination.
Frequently Asked Questions
How does it compare with methyl 6-bromo-1-naphthoate?
Both are used as C-6 electrophiles in palladium-catalysed couplings with similar reactivity. The triflate is made directly from the hydroxy precursor, while the bromide needs a halogenated starting material; the choice usually depends on the available precursor and the coupling conditions.
What should be watched in coupling reactions?
Strong aqueous base and prolonged heating can cleave the triflate back to the phenol and saponify the methyl ester. Milder bases, limited water and monitoring of the hydroxy by-product help keep yields consistent.
How should it be stored?
Keep the container tightly closed in a cool, dry place, protected from moisture and away from strong bases and nucleophiles. Follow the storage conditions on the SDS and COA.
What is the CAS number of 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester?
The CAS Registry Number of 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester is 255050-65-8. 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester is also known as 1-Naphthalenecarboxylic acid, 6-[[(trifluoromethyl)sulfonyl]oxy]-, methylester.
What is the molecular formula and molecular weight of 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester?
The molecular formula of 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester is C13H9F3O5S, and its molecular weight is 334.27 g/mol.
What is 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester used for?
KingPharm supplies this aryl triflate as an intermediate for the following uses:
Which quality documents are available for 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester?
The following documents are available for 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester: Certificate of Analysis (COA); Product specification. Contact KingPharm to request the documents for a specific batch.
How can I request a quotation for 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester?
Send an inquiry for 6-[[(Trifluoromethyl)Sulfonyl]Oxy]-1-Naphthalenecarboxylic Acid Methyl Ester (CAS 255050-65-8) with the required quantity, target specification, destination country and any documentation requirements. KingPharm will confirm availability, packaging, lead time and price.
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