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Chemical Structure| 1810-71-5 Chemical Structure| 1810-71-5
Chemical Structure| 1810-71-5

6-Bromo-2-chloroquinoline

CAS No.: 1810-71-5

6-Bromo-2-chloroquinoline is an important quinoline derivative with potential applications in antibacterial, antiviral, and anti-inflammatory drug development. Its bromine and chlorine substitution provides strong chemical reactivity, making it an ideal intermediate in organic synthesis and medicinal chemistry research.

4.5 *For Research Use Only !

Cat. No.: A286556 Purity: 98%

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Product Details of [ 1810-71-5 ]

CAS No. :1810-71-5
Formula : C9H5BrClN
M.W : 242.50
SMILES Code : ClC1=NC2=CC=C(Br)C=C2C=C1
MDL No. :MFCD04115272
InChI Key :YXRDWUJAJLDABJ-UHFFFAOYSA-N
Pubchem ID :12894086

Safety of [ 1810-71-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 1810-71-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1810-71-5 ]

[ 1810-71-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1810-71-5 ]
  • [ 791626-58-9 ]
YieldReaction ConditionsOperation in experiment
58% With acetamide; potassium carbonate; at 200℃; for 2h; Part D. Preparation of 6-bromo-2-aminoquinoline.; [00797] The product from Part C (173mg, 0.713mmol), acetamide (843mg, 14.27mmol) and potassium carbonate (493mg, 3.57mmol) were combined and heated at 200 0C for 2h. Cooled to room temperature, whereupon it solidified. Dissolved in a mixture of CHCl3 and water. Aqueous layer was extracted twice more with CHCI3, extracts were combined, washed with brine, dried over Na2SOφ filtered and concentrated under vacuum. Purification by silica gel column chromatography eluting with MeOH/CHCl3 gave title compound (92mg, 58 %).
58% [00539] Part D. Preparation of 6-bromo-2-aminoquinoline.; [00540] The product from Part C (173mg, 0.713mmol), acetamide (843mg, 14.27mmol) and potassium carbonate (493mg, 3.57mmol) were combined and heated at 200 0C for 2h. Cooled to room temperature, whereupon it solidified. Dissolved in a mixture of CHCI3 and water. Aqueous layer was extracted twice more with CHCI3, extracts were combined, washed with brine, dried over Na2SOφ filtered and concentrated under vacuum. Purification by silica gel column chromatography eluting with MeOH/CHCl3 gave title compound (92mg, 58 %).
34% With acetamide; potassium carbonate; at 200℃; for 2h; A mixture of 6-bromo-2-chloro-quinoline (2.0 g, 8.3 mmol), acetamide (9.74 g, 165 mmol) and potassium carbonate (3.4 g, 25 mmol) was heated at 200 C for 2 h. The reaction mixture was allowed to cool to rt whereupon the mixture solidified. The residue was taken up in DCM (15 ml_) and water (10 ml_), and the layers separated. The aqueous layer was extracted with DCM (2 x 15 ml_), the combined organic extracts were washed with brine, dried (MgSCU) and concentrated under vacuum to yield the title compound as a beige solid (780 mg, 34 %).1H NMR dH(400 MHz, Chloroform-d) 8.01 (d, J = 8.6 Hz, 1 H), 7.83 - 7.78 (m, 1 H), 7.78 - 7.73 (m, 1 H), 7.61 (dd, J = 8.9, 2.2 Hz, 1 H), 7.51 (d, J = 8.9 Hz, 1 H), 4.94 (s, 2H); LCMS (Method B): 1.10 min, (222.9/224.9, MH+).
 

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