| Identification | More | [Name]
Cyclopentyl bromide | [CAS]
137-43-9 | [Synonyms]
AKOS BBS-00004279
BROMOCYCLOPENTANE
CYCLOPENTYL BROMIDE
bromo-cyclopentan
Bromocylopentane
Cyclopentane,bromo-
Cyclopentane Bromide
Bromocyclopentane,98%
1-Bromocyclopentane
BROMOCYCLOPENTANE, STAB.
CYCLOPENTYL BROMIDE, 98+%
1-BROMOPENTAMETHYLENE | [EINECS(EC#)]
205-294-6 | [Molecular Formula]
C5H9Br | [MDL Number]
MFCD00001359 | [Molecular Weight]
149.03 | [MOL File]
137-43-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to yellow liquid | [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 | [color ]
Clear yellow to light brown | [Specific Gravity]
1.39 | [Stability:]
Stable. Flammable. Incompatible with strong oxidizing agents, strong bases. | [Water Solubility ]
Immiscible with water. | [Detection Methods]
GC | [BRN ]
1209256 | [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]
137-43-9(EPA Substance) |
| Safety Data | Back Directory | [Risk Statements ]
R10:Flammable. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29035990 |
| Hazard Information | Back Directory | [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 (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 ℃ 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 ℃; 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 ℃/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 |
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