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CS-W001157 4
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3-Bromo-N,N-dimethylbenzenesulfonamide

  • CAS No. 153435-80-4

  • Cat. No. CS-0196818
  • Purity≥98%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

3-Bromo-N,N-dimethylbenzenesulfonamide|CS-0196818

Structure of 153435-80-4

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General Information

  • CAS No. 153435-80-4
  • Cat. No. CS-0196818
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀BrNO₂S
  • Molecular Weight 264.14
  • Synonym(s) 3-BROMO,N, N-DIMETHYLBENZENESULFONAMIDE
  • SMILES CN(C)S(=O)(=O)C1=CC=CC(=C1)Br

Description

3-Bromo-N,N-dimethylbenzenesulfonamide is a bench-stable sulfonamide featuring a bromine substituent at the meta position, enabling direct functionalization in cross-coupling reactions. The dimethylamino group enhances solubility and electronic modulation, while the sulfonamide scaffold provides robustness under standard reaction conditions. This compound serves as a key intermediate in medicinal chemistry and materials synthesis.

Application

3-Bromo-N,N-dimethylbenzenesulfonamide serves as a versatile building block in medicinal chemistry, enabling late-stage functionalization via palladium-catalyzed cross-coupling reactions. The bromo group exhibits high reactivity in Suzuki, Stille, and Negishi couplings, while the sulfonamide moiety provides polarity and hydrogen-bonding capacity. Its bench-stable crystalline form facilitates handling, purification, and integration into complex molecule synthesis.

Synthesis

  • Route1
    • In-stock
      3-Bromobenzenesulfonyl chloride|CS-W007356
      2905-24-0
    • null|null
      124-40-3
    • ~95%
    • In-stock
      3-Bromo-N,N-dimethylbenzenesulfonamide|CS-0196818
      153435-80-4

    References

    • SGX PHARMACEUTICALS, INC. Patent: WO2006/15124 A2, 2006 ; Location in patent: Page/Page column 93 ; WO 2006/015124 A2
  • Route2
    • In-stock
      3-Bromobenzenesulfonyl chloride|CS-W007356
      2905-24-0
    • null|null
      506-59-2
    • ~90%
    • In-stock
      3-Bromo-N,N-dimethylbenzenesulfonamide|CS-0196818
      153435-80-4

    References

    • Kyowa Hakko Kirin Co., Ltd. Patent: EP2090570 A1, 2009 ; Location in patent: Page/Page column 82 ; EP 2090570 A1
  • Route3

    References

    • Fairley, Gary; Hall, Catherine; Greenwood, Ryan Synlett, 2013 , vol. 24, # 5 art. no. ST-2013-D0004-L, p. 570 - 574

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.38
  • LogP   1.6994
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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