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CS-W001157 4
Total: USD 88.00

5-(Benzyloxy)-2-bromobenzaldehyde

  • CAS No. 85604-06-4

  • Cat. No. CS-0040706
  • Purity≥98%
  • MDL No.MFCD03425931

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

5-(Benzyloxy)-2-bromobenzaldehyde|CS-0040706

Structure of 85604-06-4

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General Information

  • CAS No. 85604-06-4
  • Cat. No. CS-0040706
  • Purity ≥98%
  • MDL No. MFCD03425931
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₁BrO₂
  • Molecular Weight 291.14
  • Synonym(s) 5-BENZYLOXY-2-BROMOBENZALDEHYDE
  • SMILES O=CC1=CC(OCC2=CC=CC=C2)=CC=C1Br

Description

5-(Benzyloxy)-2-bromobenzaldehyde features a para-brominated aromatic ring flanked by a benzyloxy substituent and an aldehyde group, enabling direct integration into Suzuki-Miyaura cross-coupling and Ullmann-type reactions. The electron-deficient bromine facilitates palladium-catalyzed bond formation, while the benzyl ether stabilizes the reactive aldehyde under standard conditions.

Application

5-(Benzyloxy)-2-bromobenzaldehyde serves as a versatile building block for the synthesis of substituted benzimidazoles and biaryl scaffolds. The aldehyde functionality enables efficient Suzuki-Miyaura and Ullmann couplings, while the ortho-bromo group facilitates palladium-catalyzed cross-coupling reactions. Its benzyloxy substituent provides stability and orthogonal protection, simplifying purification and downstream transformations in medicinal chemistry campaigns.

Synthesis

  • Route1
    • In-stock
      2-Bromo-5-hydroxybenzaldehyde|CS-W007430
      2973-80-0
    • null|null
      100-39-0
    • ~96%
    • In-stock
      5-(Benzyloxy)-2-bromobenzaldehyde|CS-0040706
      85604-06-4

    References

    • Kim, Myung Hee; Choi, Young Lok; Heo, Jung-Nyoung; Min, Yong Ki; Kim, Seong Hwan Bulletin of the Korean Chemical Society, 2010 , vol. 31, # 7 p. 2047 - 2050
  • Route2
    • In-stock
      2-Bromo-5-hydroxybenzaldehyde|CS-W007430
      2973-80-0
    • null|null
      100-44-7
    • ~98%
    • In-stock
      5-(Benzyloxy)-2-bromobenzaldehyde|CS-0040706
      85604-06-4

    References

    • Lin, Jinshun; Zhang, Weige; Jiang, Nan; Niu, Zeyu; Bao, Kai; Zhang, Liang; Liu, Dailin; Pan, Chao; Yao, Xinsheng Journal of Natural Products, 2008 , vol. 71, # 11 p. 1938 - 1941
  • Route3
    • null|null
      158584-99-7
    • ~%
    • In-stock
      5-(Benzyloxy)-2-bromobenzaldehyde|CS-0040706
      85604-06-4

    References

    • N.V. ORGANON Patent: WO2009/37220 A1, 2009 ; Location in patent: Page/Page column 52 ; WO 2009/037220 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   3.8406
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   4

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