(Bromomethyl)cyclopentane Chemical Properties

Boiling point:

58-60 °C(Press: 15 Torr)

Density 

1.271 g/cm3

refractive index 

1.48

storage temp. 

Inert atmosphere,Room Temperature

form 

liquid

color 

Colourless to light brown

InChI

InChI=1S/C6H11Br/c7-5-6-3-1-2-4-6/h6H,1-5H2

InChIKey

XYZUWOHEILWUID-UHFFFAOYSA-N

SMILES

C1(CBr)CCCC1

CAS DataBase Reference

3814-30-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

1993

HazardClass 

3

PackingGroup 

Ⅲ

HS Code 

2902190000

(Bromomethyl)cyclopentane Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

(Bromomethyl)cyclopentane is an alkyl cyclopentyl core analog. It could be used as a substrate to synthesize (azidomethyl)cyclopentane[1].

Synthesis

The general procedure for the synthesis of bromomethylcyclopentane from cyclopentanemethanol was as follows: a mixed solution of cyclopentanemethanol (48.5 g, 484 mmol), triethylamine (88.0 mL, 631 mmol) and anhydrous tetrahydrofuran (1 L) was cooled to 4 °C and stirred under nitrogen protection. Methylsulfonyl chloride (45.0 mL, 581 mmol) was added slowly, keeping the reaction temperature below 10 °C. After addition, the reaction mixture was continued to stir at 10 °C for 1 hour. Subsequently, lithium bromide (300.0 g, 3454 mmol) was added slowly, taking care to control the exotherm. After addition, the reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, water was added to dissolve the salts and the mixture was extracted with ether. The ether layers were combined, dried with anhydrous sodium sulfate and carefully concentrated at 25 °C at 100 Torr. The crude product was purified by vacuum distillation (35 °C, 1 Torr, collecting the first fraction) to give bromomethylcyclopentane (31.4 g, 40% yield) as a colorless oil.

References

[1] Sara Sadler. “A Facile Route to Triazolopyrimidines Using a [3+2] Cycloaddition and Continuous-Flow Chemistry.” Journal of Flow Chemistry 4 3 (2014): 140–147.

(Bromomethyl)cyclopentane(3814-30-0)Related Product Information

• Bromocyclopentane
• Cyclopentane
• Methylcyclopentane
• Bromotrimethylsilane
• 1-Methylcyclopentene
• 4-Tolylboronic acid
• (Bromomethyl)cyclopropane
• 1-Bromobutane
• Cyclohexylmethyl bromide
• Bromomethyl methyl ether
• (Bromomethyl)cyclobutane
• 4-Bromomethyl-1,2-dihydroquinoline-2-one
• 1-Bromononane
• Bromoiodomethane
• 1-bromoMethanesulfonamide
• Bromomethylboronic acid, pinacol ester
• Ammonium (-)-3-bromo-8-camphorsulfonate
• D-3-BROMOCAMPHOR