Cyclohexylmethyl bromide Chemical Properties

Boiling point:

76-77 °C26 mm Hg(lit.)

Density 

1.269 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.492(lit.)

Flash point:

135 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Chloroform, Ethyl Acetate

form 

Liquid

color 

Clear light yellow

Water Solubility 

Insoluble in water.

BRN 

635738

InChI

InChI=1S/C7H13Br/c8-6-7-4-2-1-3-5-7/h7H,1-6H2

InChIKey

UUWSLBWDFJMSFP-UHFFFAOYSA-N

SMILES

C1(CBr)CCCCC1

CAS DataBase Reference

2550-36-9(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexane, (bromomethyl)-(2550-36-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-10

Safety Statements 

23-24/25-37/39-26-16

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29035990

MSDS

• Language:English Provider:Cyclohexylmethyl bromide
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Cyclohexylmethyl bromide Usage And Synthesis

Chemical Properties

Light yellow liquid

Uses

(Bromomethyl)cyclohexane is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.

Synthesis

The general procedure for the synthesis of bromomethylcyclohexane from cyclohexanemethanol is as follows: 1.4 kg of cyclohexanemethanol (colorless liquid), 8.4 L of toluene, and 969.8 g of pyridine were added to a 20 L four-neck flask. The reaction system was cooled to 0 to 10 °C, and then a mixture of 1.66 kg of phosphorus tribromide with 7 L of toluene was slowly added with controlled titration rate to keep the reaction temperature below 5 °C. The dropwise addition process was completed in about 1 hour. Subsequently, the reaction system was warmed to room temperature and the reaction was continued with stirring for 10 hours. Upon completion of the reaction, the system was cooled to below 20 °C and about 2.5 L of 5% sodium hydroxide solution was slowly added dropwise, followed by the addition of 1.85 kg of solid sodium hydroxide to form a mixture. Liquid-liquid separation was carried out and the aqueous phase was extracted twice with 4 L of toluene. The organic phases were combined and washed with saturated brine, and the washed organic phase was dried with anhydrous sodium sulfate. The dried organic phase was concentrated to give 1.73 kg of crude product. The crude product was purified by distillation under reduced pressure to give 722.8 g of bromomethylcyclohexane with 97.5% purity in 33.3% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.82 (m, 1H), 1.79-1.53 (m, 6H), 1.13-0.90 (m, 6H).

References

[1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2901 - 2910
[2] Patent: US2016/319312, 2016, A1. Location in patent: Paragraph 0083
[3] Journal of the American Chemical Society, 1926, vol. 48, p. 2392
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344
[5] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548

Cyclohexylmethyl bromide(2550-36-9)Related Product Information

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