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| | Nonafluorobutanesulfonyl fluoride Basic information |
| Product Name: | Nonafluorobutanesulfonyl fluoride | | Synonyms: | Nonafluorobutanesulfonyl fluoride, 90+%;Nonafluorobutanesulphonyl fluoride, tech. 90%;1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonic acid fluoride;Nonafluoro-1-butanesulfonic acid fluoride;Perfluoro-1-butanesulfonyl fluoride,92%;1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonylf;Perfluorobutanesulphonyl fluoride 95%;Perfluorobutyl fluoride | | CAS: | 375-72-4 | | MF: | C4F10O2S | | MW: | 302.09 | | EINECS: | 206-792-6 | | Product Categories: | Fine chemical;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;bc0001 | | Mol File: | 375-72-4.mol |  |
| | Nonafluorobutanesulfonyl fluoride Chemical Properties |
| Melting point | -110°C | | Boiling point | 64 °C (lit.) | | density | 1.682 g/mL at 25 °C (lit.) | | vapor pressure | 16.665kPa at 20℃ | | refractive index | n20/D 1.3(lit.) | | Fp | 65-66°C | | storage temp. | Keep in dark place,Sealed in dry,Store in freezer, under -20°C | | solubility | Chloroform (Sparingly), Methanol (Sparingly) | | form | Liquid | | color | Colorless to yellow | | Specific Gravity | 1.682 | | Water Solubility | Hydrolyses in water. | | Sensitive | Moisture Sensitive | | BRN | 1813589 | | Stability: | Hygroscopic | | InChIKey | LUYQYZLEHLTPBH-UHFFFAOYSA-N | | CAS DataBase Reference | 375-72-4(CAS DataBase Reference) | | NIST Chemistry Reference | Nonafluorobutanesulfonyl fluoride(375-72-4) | | EPA Substance Registry System | 1-Butanesulfonyl fluoride, 1,1,2,2,3,3,4,4,4-nonafluoro- (375-72-4) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-36/37/39-45-25 | | RIDADR | UN 3265 8/PG 2 | | WGK Germany | 3 | | F | 10-21 | | Hazard Note | Corrosive | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29049090 |
| | Nonafluorobutanesulfonyl fluoride Usage And Synthesis |
| Description | 1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl fluoride
(NfF) also called Nonafluorobutanesulfonyl fluoride is a versatile compound in organic synthesis. It can be
used as a fluoride source for the nucleophilic introduction
of fluorine, but it is also frequently applied as sulfonylation
reagent generating intermediates with strong electron withdrawing perfluorinated alkyl substituents. | | Chemical Properties | Nonafluorobutanesulfonyl fluoride is a colorless, volatile liquid that is immiscible with water but soluble in common organic solvents. It is prepared by the electrochemical fluorination of sulfolane. | | Uses | Benzynes were generated from o-(trimethylsilyl) phenols using nonafluorobutanesulfonyl fluoride (NfF) by a domino process.Nonafluorobutanesulfonyl fluoride (nonaflyl fluoride, C 4 F 9 SO 2 F, NfF) is the most widely used commercially available reagent for the synthesis of nonaflates. | | Application | Perfluoro-1-butanesulfonyl fluoride (NfF) reacts with alcohols, including phenols, to yield nonafluorobutanesulfonate esters (nonaflates). Nonaflates can be used as electrophiles in several palladium-catalyzed cross coupling reactions and in Buchwald-Hartwig amination. NfF can also be used to prepare aryl nonaflates by reacting with corresponding aryloxysilanes in the presence of fluoride ion.
| | Synthesis | NfF(Nonafluorobutanesulfonyl fluoride) is produced on industrial scale by anodic fluorination of sulfolene (1, Scheme 1),3 therefore it is a fairly cheap reagent and commercially available from several suppliers. The compound is bench-stable and storable for years, nontoxic and easy to handle.
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| | Nonafluorobutanesulfonyl fluoride Preparation Products And Raw materials |
| Raw materials | N-BUTANESULFONYL FLUORIDE-->NONAFLUORO-1-BUTANESULFONYL CHLORIDE-->Sulfolane-->1-Butanesulfonyl chloride | | Preparation Products | DIMETHYLDIFLUOROSILANE-->Perfluoro-1-octanesulfonyl fluoride-->1,1,2,2,3,3,4,4,4-Nonafluoro-N-(2-methoxyethyl)-1-butanesulfonamide-->Tetrabutyl phosphonium salt with 1,1,2,2,3,3,4,4,4-nonafluoro-1-butanesulfonic acid(1:1)-->N-(Methyl)nonafluorobutanesulfonamide-->Potassium nonafluoro-1-butanesulfonate |
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