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CS-W001157 4
Total: USD 88.00

2-Bromo-6-methylbenzaldehyde

  • CAS No. 176504-70-4

  • Cat. No. CS-0061197
  • Molecule weight199.04
  • Purity≥97%
  • MDL No.None

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

2-Bromo-6-methylbenzaldehyde|CS-0061197

Structure of 176504-70-4

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General Information

  • CAS No. 176504-70-4
  • Cat. No. CS-0061197
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO
  • Molecular Weight 199.04
  • Synonym(s) 3-Bromo-2-formyltoluene, 6-Bromo-o-tolualdehyde
  • SMILES CC1=C(C=O)C(=CC=C1)Br

Description

2-Bromo-6-methylbenzaldehyde features a bromine atom at the ortho position relative to the aldehyde group and a methyl substituent at the para position, creating a sterically hindered, electron-deficient aromatic scaffold. This combination enhances reactivity in cross-coupling processes while maintaining bench-stable handling characteristics under standard conditions.

Application

2-Bromo-6-methylbenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct incorporation of bromo and methyl substituents ortho to the aldehyde functionality. Its stability under standard reaction conditions facilitates Suzuki-Miyaura, Negishi, and Stille couplings, while the aldehyde group permits facile transformations into imines, hydrazones, or reductive amination products. The molecule’s defined regiochemistry supports efficient downstream functionalization in multi-step syntheses.

Synthesis

  • Route1
    • null|null
      74-88-4
    • ~93%
    • In-stock
      2-Bromo-6-methylbenzaldehyde|CS-0061197
      176504-70-4

    References

    • Evonik Degussa GmbH Patent: EP1894938 A1, 2008 ; Location in patent: Page/Page column 35-36 ;
  • Route2

    References

    • Dubost, Emmanuelle; Fossey, Christine; Cailly, Thomas; Rault, Sylvain; Fabis, Frederic Journal of Organic Chemistry, 2011 , vol. 76, # 15 p. 6414 - 6420
  • Route3

    References

    • Sedishev, I. P.; Agafonov, N. E.; Kutin, A. A.; Zhulin, V. M. Russian Chemical Bulletin, 1995 , vol. 44, # 11 p. 2127 - 2130 Izvestiya Akademi Nauk, Seriya Khimicheskaya, 1995 , # 11 p. 2221 - 2224

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
Precautionary Statements : P264-P270-P330-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.57002
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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