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| | Bromocyclopentane Basic information |
| | Bromocyclopentane Chemical Properties |
| Boiling point | 137-139 °C (lit.) | | density | 1.39 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.4881(lit.) | | Fp | 95 °F | | storage temp. | Store at R.T. | | solubility | Chloroform, Ethyl Acetate (Slightly) | | form | Liquid | | Specific Gravity | 1.39 | | color | Clear yellow to light brown | | Water Solubility | Immiscible with water. | | BRN | 1209256 | | Stability: | Stable. Flammable. Incompatible with strong oxidizing agents, strong bases. | | InChIKey | BRTFVKHPEHKBQF-UHFFFAOYSA-N | | LogP | 2.745 (est) | | CAS DataBase Reference | 137-43-9(CAS DataBase Reference) | | NIST Chemistry Reference | Cyclopentane, bromo-(137-43-9) | | EPA Substance Registry System | Cyclopentane, bromo- (137-43-9) |
| Risk Statements | 10 | | Safety Statements | 23-24/25-16 | | RIDADR | UN 1993 3/PG 3 | | WGK Germany | 3 | | F | 8 | | TSCA | Yes | | HazardClass | 3 | | PackingGroup | III | | HS Code | 29035990 |
| | Bromocyclopentane Usage And Synthesis |
| Chemical Properties | Bromocyclopentane is a colorless to light yellow liquid at standard temperature and pressure.It has an aroma similar to camphor. It turns brown after a long time. Soluble in ethanol, ether, insoluble in water. Halocyclopentanes can be prepared by reacting the corresponding alcohols with thionyl halides, phosphorus trihalides or hydrohalic acids. | | Uses | Bromocyclopentane is a precursor used in the preparation of cyclopentene and cyclopentanol. It is a fatty bromide, which is used as a solvent. It is used as an intermediate for the preparation of surfactant and pharmaceuticals and other organic compounds. It is also used in the production of the medicine cyclopentathiazide. | | Preparation | Bromocyclopentane is synthesized by bromination of cyclopentanol: cyclopentanol is mixed with hydrobromic acid and heated to about 170°C refluxed for 6-8h. Then distilled with water steam, the oil layer is washed with 5% sodium carbonate, then dried, filtered, fractionated and collected 136-139°C fraction is the finished product. Another method is by the reaction of cyclopentanol and phosphorus tribromide: the cyclopentanol is cooled to 0 ℃, add the newly evaporated phosphorus tribromide drop by drop, add it all at 0-5 ℃, stir for 2h, and leave it at room temperature overnight. Add water and stratify, take the oil layer water distillation. Distillate stratification, the oil layer was washed with 10% sodium bicarbonate solution, dried with anhydrous calcium chloride, filtration, filtrate distillation, collect 134-141 ℃ fraction that is bromocyclopentane. | | Reactions | Bromocyclopentane is reacted with magnesium turnings in dry tetrahydrofuran making cyclopentyl Grignard reagent, a main precursor in the synthesis of Ketamine.
Bromocyclopentane (22.0 g, 0.15 mol) was added to a soln of NaNO2 (18 g, 0.26 mol) in dry DMSO (100 mL) at 15°C and the mixture was stirred at this temperature for 3 h. The mixture was poured into ice water (250 mL) and extracted with petroleum ether (bp 35-37°C; 4 × 50 mL). The combined organic extracts were washed with H2O (4× 50 mL), dried (MgSO4), and concentrated under reduced pressure. The residue was distilled to give Nitrocyclopentane; yield: 9.9 g (58%); bp 62°C/8 Torr; nD/20 1.4538.
Synthesis of Nitrocyclopentane | | Synthesis Reference(s) | The Journal of Organic Chemistry, 54, p. 1463, 1989 DOI: 10.1021/jo00267a047 |
| | Bromocyclopentane Preparation Products And Raw materials |
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