ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Cyclic hydrocarbons 3-BROMOCYCLOHEXENE

3-BROMOCYCLOHEXENE

Product Name3-BROMOCYCLOHEXENE
CAS1521-51-3
MFC6H9Br
MW161.04
EINECS
MOL File1521-51-3.mol

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
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

110-83-8

1521-51-3

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

Chemical Properties

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MSDS

Usage And Synthesis

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