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| | N-Boc-3-bromopyrrolidine Basic information |
| | N-Boc-3-bromopyrrolidine Chemical Properties |
| Melting point | 47-52℃ | | Boiling point | 277.5±33.0 °C(Predicted) | | density | 1.379±0.06 g/cm3(Predicted) | | Fp | >110°C | | storage temp. | 2-8°C | | pka | -3.30±0.40(Predicted) | | form | solid | | Appearance | White to yellow Solid | | Water Solubility | Slightly soluble in water. | | InChI | InChI=1S/C9H16BrNO2/c1-9(2,3)13-8(12)11-5-4-7(10)6-11/h7H,4-6H2,1-3H3 | | InChIKey | QJTKPXFJOXKUEY-UHFFFAOYSA-N | | SMILES | N1(C(OC(C)(C)C)=O)CCC(Br)C1 | | CAS DataBase Reference | 939793-16-5 |
| Hazard Codes | Xn,N | | Risk Statements | 22-36-50 | | Safety Statements | 26-61 | | RIDADR | UN 3077 9/PG 3 | | WGK Germany | 3 | | HazardClass | 9 | | HS Code | 2933998090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Acute 1
Eye Irrit. 2 |
| | N-Boc-3-bromopyrrolidine Usage And Synthesis |
| Uses | (±)-1-Boc-3-bromopyrrolidine is used in organic synthesis. | | Synthesis | General procedure for the synthesis of N-BOC-3-bromopyrrolidine from (RS)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine: (RS)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine (3.00 g) was dissolved in THF (90 mL), and triphenylphosphine (12.4 g) and carbon tetrabromide (15.7 g) were added sequentially. Subsequently, THF (90 mL) was added slowly dropwise and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the organic solvent was removed by rotary evaporation. The residue was extracted with ethyl acetate (4 x 50 mL), and the combined organic phases were washed with deionized water, dried over anhydrous sodium sulfate, and rotary evaporated again to dryness. Finally, the residue was purified by fast column chromatography (silica gel, cyclohexane/ethyl acetate 80/20) to afford the target product, (RS)-1-tert-butoxycarbonyl-3-bromopyrrolidine, in 80% yield as a yellow oil.1H-NMR (300 MHz, DMSO-d6, δ ppm relative to TMS): δ 4.85 (1H, m) 3.70-3.59 (1H, m), 3.55-2.10 (5H, m), 1.35 (9H, s). | | References | [1] Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7520 - 7523
[2] Patent: WO2007/118830, 2007, A1. Location in patent: Page/Page column 139
[3] Patent: WO2010/51245, 2010, A1. Location in patent: Page/Page column 38
[4] Patent: WO2010/77624, 2010, A1. Location in patent: Page/Page column 37
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 13, p. 5613 - 5637 |
| | N-Boc-3-bromopyrrolidine Preparation Products And Raw materials |
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