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2-Bromo-1-(2-bromophenyl)ethan-1-one

  • CAS No. 49851-55-0

  • Cat. No. CS-0181796
  • Molecule weight277.94
  • Purity≥96%
  • MDL No.MFCD00044660

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

2-Bromo-1-(2-bromophenyl)ethan-1-one|CS-0181796

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General Information

  • CAS No. 49851-55-0
  • Cat. No. CS-0181796
  • Purity ≥96%
  • MDL No. MFCD00044660
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆Br₂O
  • Molecular Weight 277.94
  • Synonym(s) 2-BROMO-1-(2-BROMO-PHENYL)-ETHANONE
  • SMILES BrC1=CC=CC=C1C(CBr)=O

Description

2-Bromo-1-(2-bromophenyl)ethan-1-one features a sterically hindered dibrominated aryl ketone core, enabling direct incorporation into transition-metal-catalyzed cross-coupling reactions. This bench-stable reagent facilitates efficient construction of complex biaryl architectures under standard conditions.

Application

2-Bromo-1-(2-bromophenyl)ethan-1-one serves as a versatile building block in synthetic organic chemistry, enabling efficient construction of biaryl and heterocyclic scaffolds. Its dual bromine functionalities facilitate palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with high regioselectivity. The compound exhibits good bench stability and compatibility with standard reaction conditions, allowing straightforward purification and integration into multi-step syntheses for pharmaceutical and agrochemical intermediates.

Synthesis

  • Route1

    References

    • ANACOR PHARMACEUTICALS, INC. Patent: WO2008/157726 A1, 2008 ; Location in patent: Page/Page column 136 ; WO 2008/157726 A1
  • Route2

    References

    • Tada, Norihiro; Ban, Kazunori; Hirashima, Shin-Ichi; Miura, Tsuyoshi; Itoh, Akichika Organic and Biomolecular Chemistry, 2010 , vol. 8, # 20 p. 4701 - 4704
  • Route3

    References

    • Jiang, Qing; Sheng, Wenbing; Guo, Cancheng Green Chemistry, 2013 , vol. 15, # 8 p. 2175 - 2179

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.0267
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   2

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