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CS-W001157 4
Total: USD 88.00

2,6-Dibromo-4-methylbenzaldehyde

  • CAS No. 88174-23-6

  • Cat. No. CS-0106376
  • Molecule weight277.94
  • Purity≥98%
  • MDL No.MFCD11040412

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

2,6-Dibromo-4-methylbenzaldehyde|CS-0106376

Structure of 88174-23-6

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General Information

  • CAS No. 88174-23-6
  • Cat. No. CS-0106376
  • Purity ≥98%
  • MDL No. MFCD11040412
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₆Br₂O
  • Molecular Weight 277.94
  • Synonym(s) Benzaldehyde,2,6-dibromo-4-methyl
  • SMILES O=CC1=C(Br)C=C(C)C=C1Br

Description

2,6-Dibromo-4-methylbenzaldehyde features a sterically hindered aromatic core with two bromine substituents flanking a methyl group and an aldehyde at the para position. This electron-deficient scaffold enables direct coupling in cross-coupling reactions and serves as a robust building block for functionalized heterocycles and advanced synthetic intermediates under standard conditions.

Application

2,6-Dibromo-4-methylbenzaldehyde serves as a valuable building block for the synthesis of substituted benzaldehydes and heterocyclic scaffolds. Its ortho-bromine substituents enable subsequent palladium-catalyzed cross-coupling reactions, while the aldehyde group facilitates condensation and derivatization. The methyl group provides steric and electronic modulation, enhancing stability and selectivity in functional group transformations. This compound is bench-stable and readily purified by recrystallization, making it well-suited for use in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • In-stock
      1,3-Dibromo-5-methylbenzene|CS-W012650
      1611-92-3
    • null|null
      68-12-2
    • ~63%
    • In-stock
      2,6-Dibromo-4-methylbenzaldehyde|CS-0106376
      88174-23-6

    References

    • Lulinski, Sergiusz; Serwatowski, Janusz Journal of Organic Chemistry, 2003 , vol. 68, # 13 p. 5384 - 5387
  • Route2
    • null|null
      4885-02-3
    • In-stock
      1,3-Dibromo-5-methylbenzene|CS-W012650
      1611-92-3
    • ~2%
    • 2,4-Dibromo-6-methylbenzaldehyde|CS-0515858
      1427565-04-5
    • In-stock
      2,6-Dibromo-4-methylbenzaldehyde|CS-0106376
      88174-23-6

    References

    • Ohsawa, Kosuke; Yoshida, Masahito; Doi, Takayuki Journal of Organic Chemistry, 2013 , vol. 78, # 7 p. 3438 - 3444

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
Precautionary Statements : P264-P280-P302+P352-P362+P364

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   3.33252
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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