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Bromocyclopentane

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CAS:137-43-9
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CAS:137-43-9
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CAS:137-43-9
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CAS:137-43-9
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Bromocyclopentane manufacturers

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  • Bromocyclopentane
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  • 2023-08-16
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Bromocyclopentane Basic information
Product Name:Bromocyclopentane
Synonyms:1-Bromocyclopentane;BROMOCYCLOPENTANE, STAB.;CYCLOPENTYL BROMIDE, 98+%;1-BROMOPENTAMETHYLENE;Cyclopentane Bromide;Bromocyclopentane,98%;Cyclopentyl bromide ,99%;Bromocyclopentane,Cyclopentyl bromide
CAS:137-43-9
MF:C5H9Br
MW:149.03
EINECS:205-294-6
Product Categories:Pyridines ,Halogenated Heterocycles;Pharmaceutical Intermediates;CHLORO ALKANE COMPOUNDS
Mol File:137-43-9.mol
Bromocyclopentane Structure
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 Gravity1.39
color Clear yellow to light brown
Water Solubility Immiscible with water.
BRN 1209256
Stability:Stable. Flammable. Incompatible with strong oxidizing agents, strong bases.
InChIKeyBRTFVKHPEHKBQF-UHFFFAOYSA-N
LogP2.745 (est)
CAS DataBase Reference137-43-9(CAS DataBase Reference)
NIST Chemistry ReferenceCyclopentane, bromo-(137-43-9)
EPA Substance Registry SystemCyclopentane, bromo- (137-43-9)
Safety Information
Risk Statements 10
Safety Statements 23-24/25-16
RIDADR UN 1993 3/PG 3
WGK Germany 3
8
TSCA Yes
HazardClass 3
PackingGroup III
HS Code 29035990
MSDS Information
ProviderLanguage
Cyclopentyl bromide English
SigmaAldrich English
ACROS English
ALFA English
Bromocyclopentane Usage And Synthesis
Chemical PropertiesBromocyclopentane 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.
UsesBromocyclopentane 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.
PreparationBromocyclopentane 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.
ReactionsBromocyclopentane 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 of Nitrocyclopentane
Synthesis Reference(s)The Journal of Organic Chemistry, 54, p. 1463, 1989 DOI: 10.1021/jo00267a047
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