| Identification | More | [Name]
3-Bromocumene | [CAS]
5433-01-2 | [Synonyms]
1-BROMO-3-ISOPROPYLBENZENE
3-BROMOCUMENE
3-BROMOISOPROPYLBENZENE
3-ISOPROPYLBROMOBENZENE
1-Bromo-3-(1-methylethyl)benzene
Benzene,1-bromo-3-(1-methylethyl)-
cumene,3-bromo-
m-bromocumene
m-bromoisopropylbenzene
3-Bromocumene~3-Isopropylbromobenzene
1-Bromo-3-isopropylbenzene (3-Bromoisopropylbenzene, 3-Bromcumene | [Molecular Formula]
C9H11Br | [MDL Number]
MFCD01318112 | [Molecular Weight]
199.09 | [MOL File]
5433-01-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
-10°C (estimate) | [Boiling point ]
52-53°C 0,8mm | [density ]
1,285 g/cm3 | [refractive index ]
1.5302 | [Fp ]
52-53°C/0.8mm | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
clear liquid | [color ]
Colorless to Light orange to Yellow | [Water Solubility ]
Difficult to mix in water. | [BRN ]
1858092 | [InChI]
InChI=1S/C9H11Br/c1-7(2)8-4-3-5-9(10)6-8/h3-7H,1-2H3 | [InChIKey]
GBSGGFCCQZUXNB-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC=CC(C(C)C)=C1 | [CAS DataBase Reference]
5433-01-2(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to yellow liquid | [Uses]
It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 25, p. 1691, 1960 DOI: 10.1021/jo01080a001 | [Synthesis]
2-Bromo-4-isopropylaniline (2.65 g, 12.4 mmol, 1.0 eq.) was added to a mixed solution consisting of 96% ethanol (23 mL) and concentrated sulfuric acid (2.5 mL) over 15 min. The reaction system was cooled to -5 °C under vigorous stirring and an aqueous solution of sodium nitrite (1.42 g, 20.7 mmol, 1.67 eq.) was added dropwise over 1 h (3 mL). After the dropwise addition, stirring was continued at -5 °C for 30 min. Subsequently, copper powder (12.0 g) was added and the reaction mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was filtered through a glass sand core funnel. The filtrate was poured into cold water (60 mL) and the organic product was extracted with dichloromethane (4 x 50 mL). The organic extracts were combined, dried with anhydrous potassium carbonate and concentrated under reduced pressure. The residue was purified by fractional distillation under reduced pressure (11 mmHg, 89-90 °C) to give 3-isopropylbromobenzene (1.91 g, 77% yield) as a yellow oil. | [References]
[1] Synthesis (Germany), 2016, vol. 48, # 19, p. 3301 - 3308
[2] Journal of the Chemical Society, 1939, p. 1299,1301
[3] Journal of Organic Chemistry, 1939, vol. 4, p. 20,26
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797 |
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