Bromocyclopentane Property

Boiling point:

137-139 °C (lit.)

Density 

1.39 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4881(lit.)

Flash point:

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)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

Bromocyclopentane Chemical Properties,Usage,Production

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