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| | Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate Basic information |
| | Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate Chemical Properties |
| Melting point | 100 °C | | storage temp. | -20°C | | solubility | DMF: 0.4 g/mL, clear | | form | Powder | | color | White to off-white | | Water Solubility | moderately soluble | | Sensitive | Moisture Sensitive | | BRN | 7845702 | | Stability: | Moisture Sensitive | | Major Application | peptide synthesis | | InChI | InChI=1S/C12H24BrN3P.F6P/c13-17(14-7-1-2-8-14,15-9-3-4-10-15)16-11-5-6-12-16;1-7(2,3,4,5)6/h1-12H2;/q+1;-1 | | InChIKey | CYKRMWNZYOIJCH-UHFFFAOYSA-N | | SMILES | [P+5]([F-])([F-])([F-])([F-])([F-])[F-].[P+](N1CCCC1)(N1CCCC1)(N1CCCC1)Br | | CAS DataBase Reference | 132705-51-2(CAS DataBase Reference) |
| Hazard Codes | Xi,C | | Risk Statements | 36/37/38-34 | | Safety Statements | 26-36-45-36/37/39-27 | | WGK Germany | 3 | | F | 10-21 | | HS Code | 2933 99 80 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B |
| | Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate Usage And Synthesis |
| Chemical Properties | white to off-white powder | | Uses | A stable reagent for the coupling of N-Methylamino acids in peptide synthesis. | | Uses | It can be used as a coupling reagent:
- For Suzuki–Miyaura cross-coupling of phenols and arylboronic acids to synthesize biaryls and heterobiaryls.
- To functionalize pyrimidines (synthesized from 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) via the Kappe dehydrogenation) by using various nucleophiles.
- To synthesize formamidines by coupling with various primary amines and N,N-diisopropylethylamine.
It can also be used as an activating reagent:
- For the activation of C-OH bond in tautomerizable heterocycles to form the phosphonium salt which aids the Sonogashira coupling of heterocycles with various alkynes.
- For the one–pot activation of C-O bond in phenols and further coupling reaction with phosphine oxide or phosphite to form C-P bonds.
| | reaction suitability | reaction type: Coupling Reactions |
| | Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate Preparation Products And Raw materials |
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