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Benzaldehyde, 2-bromo-3-methyl-

  • CAS No. 109179-31-9

  • Cat. No. CS-0031379
  • Purity≥96%
  • MDL No.MFCD18392002

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

Benzaldehyde, 2-bromo-3-methyl-|CS-0031379

Structure of 109179-31-9

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General Information

  • CAS No. 109179-31-9
  • Cat. No. CS-0031379
  • Purity ≥96%
  • MDL No. MFCD18392002
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO
  • Molecular Weight 199.04
  • Synonym(s) None
  • SMILES O=CC1=CC=CC(C)=C1Br

Description

2-Bromo-3-methylbenzaldehyde features a strategically positioned bromine atom and methyl group on the aromatic ring, enabling selective functionalization in cross-coupling reactions. This electron-deficient aldehyde integrates readily into complex molecular architectures under standard conditions.

Application

2-Bromo-3-methylbenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling direct incorporation of bromo and methyl substituents adjacent to an aldehyde handle. Its reactivity facilitates palladium-catalyzed cross-coupling reactions, including Suzuki-Miyaura and Stille couplings, with excellent functional group tolerance. The aldehyde group supports subsequent transformations such as imine formation, oxime derivatization, or reductive amination, while the molecule exhibits good bench stability and ease of purification, making it well-suited for iterative synthetic sequences and scale-up.

Synthesis

  • Route1

    References

    • Schulte, Birte; Froehlich, Roland; Studer, Armido Tetrahedron, 2008 , vol. 64, # 52 p. 11852 - 11859
  • Route2

    References

    • AJINOMOTO CO., INC. Patent: US2011/82109 A1, 2011 ; Location in patent: Page/Page column 33 ; US 20110082109 A1
  • Route3

    References

    • Miyano, Sotaro; Fukushima, Hiroshi; Inagawa, Hideho; Hashimoto, Harukichi Bulletin of the Chemical Society of Japan, 1986 , vol. 59, p. 3285 - 3286

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

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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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