| Identification | Back Directory | [Name]
3-BROMO-5-CHLOROTOLUENE | [CAS]
329944-72-1 | [Synonyms]
3-BROMO-5-CHLOROTOLUENE
3-bromo-5-chlorotlouene
3-Bromo-5-chlorotoluene 98%
3-Chloro-5-methyl-bromobenzene
1-BROMO-3-CHLORO-5-METHYLBENZENE
Benzene,1-bromo-3-chloro-5-methyl- | [Molecular Formula]
C7H6BrCl | [MDL Number]
MFCD08437596 | [MOL File]
329944-72-1.mol | [Molecular Weight]
205.48 |
| Chemical Properties | Back Directory | [Melting point ]
25℃ | [Boiling point ]
222.3±20.0℃ (760 Torr) | [density ]
1.535±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
101.5±11.9℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Ethyl Acetate | [form ]
Solid | [color ]
Pale Yellow | [InChI]
InChI=1S/C7H6BrCl/c1-5-2-6(8)4-7(9)3-5/h2-4H,1H3 | [InChIKey]
YRIKDGJWRMHTJP-UHFFFAOYSA-N | [SMILES]
C1(Br)=CC(C)=CC(Cl)=C1 |
| Hazard Information | Back Directory | [Uses]
3-Bromo-5-chlorotoluene is a reagent used in the synthesis of novel benzophenones towards the discovery of potent, next generation HIV nonnucleoside reverse transcriptase inhibitors. | [Synthesis]
2-Bromo-6-chloro-4-methylaniline (30 mmol) was used as a starting material, which was dissolved in a mixed solution of acetic acid (60 mL), water (25 mL), and concentrated hydrochloric acid (7 mL), and the reaction system was subsequently cooled to 5 °C. A solution of sodium nitrite (48 mmol, 3.31 g) in water (12 mL) was added slowly and dropwise while keeping the temperature below 5 °C. After the dropwise addition, the reaction mixture was continued to be stirred at 5-10 °C for 2 hours. Subsequently, the reaction solution was poured into a 50% hypophosphite solution pre-cooled to 0 °C and stirred for 48 h at room temperature. Upon completion of the reaction, extraction was carried out with dichloromethane (3 x 120 mL). The organic phases were combined, washed with saturated saline (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. Finally, the residue was purified by fast column chromatography to obtain the target product 3-bromo-5-chlorotoluene. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 22, p. 5568 - 5572
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882 |
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