3-BROMOCYCLOHEXENE Chemical Properties

Melting point:

131-134 °C

Boiling point:

57-58 °C/12 mmHg (lit.)

Density 

1.4 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

130 °F

storage temp. 

-20°C

form 

Solid

color 

White to off-white

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

635953

InChI

InChI=1S/C6H9Br/c7-6-4-2-1-3-5-6/h2,4,6H,1,3,5H2

InChIKey

AJKDUJRRWLQXHM-UHFFFAOYSA-N

SMILES

C1CCCC(Br)C=1

CAS DataBase Reference

1521-51-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38

Safety Statements 

26-36

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

F 

10

HazardClass 

3

PackingGroup 

III

HS Code 

29038900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-BROMOCYCLOHEXENE Usage And Synthesis

Chemical Properties

clear colorless to yellow liquid

Uses

3-Bromocyclohexene was used in the synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine. It was also used in the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol and allo-inocitol.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3863, 1985 DOI: 10.1016/S0040-4039(00)89271-0

Synthesis

The general procedure for the synthesis of 3-bromocyclohexene from cyclohexene was as follows: cyclohexene (8.2 g, 0.1 mol) and N-bromosuccinimide (NBS, 21.4 g, 0.12 mol) were dissolved in carbon tetrachloride (CCl4, 100 mL) at room temperature, and azobisisobutyronitrile (AIBN, 3.3 g, 20 mmol) was subsequently added as initiator. . The reaction mixture was heated to reflux for 3 hours. Upon completion of the reaction, the reaction mixture was washed sequentially with sodium sulfite (Na2SO3) solution, saturated sodium bicarbonate (NaHCO3) solution and brine to remove unreacted reagents and by-products. The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to afford the crude product 3-bromocyclohexene (8.5 g, 53% yield). The product did not require further purification and could be used directly in the subsequent reaction.

References

[1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 20, p. 3751 - 3761
[2] Tetrahedron Letters, 2003, vol. 44, # 9, p. 1815 - 1817
[3] Journal of Organic Chemistry, 2014, vol. 79, # 18, p. 8786 - 8799
[4] Journal of the American Chemical Society, 2016, vol. 138, # 42, p. 13830 - 13833
[5] Journal of Chemical Research, Miniprint, 1981, # 2, p. 569 - 582

3-BROMOCYCLOHEXENE(1521-51-3)Related Product Information

• 3-BROMOCYCLOHEXENE
• Cyclohexene
• BROMOCONDURITOL
• (+/-)-bromocyclohexene
• 4-Bromocyclohexene
• 1-Bromocyclohexene
• RARECHEM AQ BC 9075
• RARECHEM AQ BC 9103
• RARECHEM AQ BC 9101
• RARECHEM AQ BC 9072
• 4,8-DIBROMO-2,6-DIPHENYLBICYCLO[3.3.1]NONA-2,6-DIENE
• RARECHEM AQ BC 9073
• RARECHEM AQ BC 9016
• RARECHEM AQ BC 9074
• RARECHEM AQ BC 9054
• RARECHEM AQ TC 8016
• RARECHEM AL BO 2062
• 2,6-DIBROMO-4,8-DICYANOTRICYCLO[3.3.1.0(1,5)]NONA-3,7-DIENE