N-氟二苯磺酰胺N-氟代双苯磺酰胺N-氟苯磺酰胺
N-Fluorobenzenesulfonimide
CAS: 133745-75-2;145490-75-1
Molecular Formula: C12H10FNO4S2
N-氟二苯磺酰胺N-氟代双苯磺酰胺N-氟苯磺酰胺 - Names and Identifiers
| Name | N-Fluorobenzenesulfonimide |
| Synonyms | NFSI N-FLUOROBENZENESULFONAMIDE N-FLUOROBENZENESULFONIMIDE N-Fluorobenzenesulfonimide N-fluorobenzenesulfonamide N-Fluorobenzenesulphonimide N-FLUOROBENZENESULPHONIMIDE N-Fluorobenzene sulfonimide N-FLUORODIBENZENESULFONAMIDE N-FluorobenzenesulfonMide (NFA) N-Fluorobenzenesulfonmide (NFSI) N-FLUOROBIS(PHENYLSULFONYL)AMINE N-Fluorobenzenesulfonimide(NFSI) 3,4-bis(trifluoromethyl)benzoic acid |
| CAS | 133745-75-2 145490-75-1 |
| EINECS | 000-000-0 |
| InChI | InChI=1/C9H4F6O2/c10-8(11,12)5-2-1-4(7(16)17)3-6(5)9(13,14)15/h1-3H,(H,16,17) |
| InChIKey | RLKHFSNWQCZBDC-UHFFFAOYSA-N |
N-氟二苯磺酰胺N-氟代双苯磺酰胺N-氟苯磺酰胺 - Physico-chemical Properties
| Molecular Formula | C12H10FNO4S2 |
| Molar Mass | 315.34 |
| Density | 1.4466 (estimate) |
| Melting Point | 114-116°C |
| Boling Point | 471.4±28.0 °C(Predicted) |
| Flash Point | 110℃ |
| Solubility | Very soluble in acetonitrile, dichloromethane or THF and less soluble in toluene. |
| Vapor Presure | 0.0162mmHg at 25°C |
| Appearance | Crystallization |
| Color | white |
| BRN | 5348902 |
| pKa | -32.45±0.70(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.424 |
| MDL | MFCD00144885 |
| Use | Palladium-catalyzed enantioselective fluorination for tert-butoxycarbonyllactone and lactam compounds. It can also be used for the electrophilic difluorination of dihalopyridine compounds under the action of butyl lithium, and for the direct conversion of alcohols under the action of triphenylphosphine into bisphenylsulfonimide compounds. Stable and easy-to-treat crystalline substances, easy to convert F into enolates and negative carbon ions. |
N-氟二苯磺酰胺N-氟代双苯磺酰胺N-氟苯磺酰胺 - Risk and Safety
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10 |
| TSCA | No |
| HS Code | 29242990 |
| Hazard Note | Oxidising Agent |
| Hazard Class | IRRITANT |
N-氟二苯磺酰胺N-氟代双苯磺酰胺N-氟苯磺酰胺 - Reference Information
| introduction | NFSI is a new, stable and mild fluorination reagent, which can introduce fluorine atoms into the ortho position of carbonyl groups in organic molecules, and can treat electron-rich aromatic compounds, Enol silyl ether, Enol lithium salt, etc. carry out monofluorination reaction. At present, the research hotspots are the nazarov cyclization reaction that forms a five-membered ring under the catalysis of iron or cobalt, and the asymmetric catalysis of enantioselective α-fluorination. |
| there are two main production methods for preparing | N-fluorobenzenesulfonamide. the first Differding method is as follows: dibenzenesulfonamide is dissolved in acetonitrile, sodium fluoride is added, the mixed solution is cooled to -35 ℃, the fluorine-nitrogen mixture with a volume ratio of 1:10 is introduced into the mixture for 2 hours, and nitrogen is purged for 2 hours, white crystals were obtained by filtration, evaporation and recrystallization with a yield of 74%. The other is the Wanger method. The specific preparation process is as follows: diphenylsulfonimide sodium salt is dissolved in water/acetonitrile or pure water, and after cooling, a fluorine-nitrogen mixture with V(F2):V(N2)= 1:10 is introduced. After the reaction, the reactor is purged with nitrogen, and the N-fluorobenzenesulfonamide product is obtained through filtration, water washing and drying, with a yield of up to 94%. |
| Use | For palladium-catalyzed enantioselective fluorination of tert-butoxy carbonyl lactone and lactam compounds. It can also be used for the electrophilic difluorination of dihalopyridine compounds under the action of butyl lithium, and for the direct conversion of alcohols under the action of triphenylphosphine into bisphenylsulfonimide compounds. Stable and easy-to-treat crystalline substances, easy to convert F into enolates and negative carbon ions. A stable and mild fluorination reagent for monofluorination of electron-rich aromatic compounds, enol silyl ether, enol lithium salt, etc.; NFSI can perform electrophilic fluorination on substrates such as aldehydes, ketones, esters, etc. under the catalysis of chiral organic small molecules, with high enantioselectivity; Under the catalysis of chiral metal complexes, NFSI can perform electrophilic fluorination on substrates such as aldehydes, ketones, esters, etc, the enantioselectivity is also high; as a fluorine reagent, it can be used to add double bonds; as a fluorine reagent, it can be used to fluorinate aromatic compounds; palladium-catalyzed enantioselective fluorination of tert-butoxycarbonyllactone and lactam compounds; used for the electrophilic difluorination of dihalopyridine compounds under the action of butyl lithium and the direct conversion of alcohols under the action of triphenylphosphine into bisphenylsulfonimide compounds Mainly as a fluorinating agent, It can perform monofluorination on electron-rich aromatic compounds, enol silyl ether, enol lithium salt, etc. |
Last Update：2024-04-09 21:00:56
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