| Identification | More | [Name]
3-BROMOCYCLOHEXENE | [CAS]
1521-51-3 | [Synonyms]
1,2,3,4-TETRAHYDROBROMOBENZENE
2-CYCLOHEXEN-1-YL BROMIDE
(+/-)-3-BROMOCYCLOHEXENE
3-BROMOCYCLOHEXENE
TIMTEC-BB SBB007864
1-Bromo-2-cyclohexene
2-Cyclohexenyl bromide
3-Bromo-1-cyclohexene
3-BROMOCYCLOHEXENE, TECH., 90% | [Molecular Formula]
C6H9Br | [MDL Number]
MFCD00013775 | [Molecular Weight]
161.04 | [MOL File]
1521-51-3.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to yellow liquid | [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.)
| [Fp ]
130 °F
| [storage temp. ]
2-8°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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [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 |
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