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CS-W001157 4
Total: USD 88.00

2-(2-Bromo-5-methoxyphenyl)acetonitrile

  • CAS No. 27387-23-1

  • Cat. No. CS-0041927
  • Purity≥95%
  • MDL No.MFCD09927439

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

2-(2-Bromo-5-methoxyphenyl)acetonitrile|CS-0041927

Structure of 27387-23-1

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General Information

  • CAS No. 27387-23-1
  • Cat. No. CS-0041927
  • Purity ≥95%
  • MDL No. MFCD09927439
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈BrNO
  • Molecular Weight 226.07
  • Synonym(s) None
  • SMILES COC1=CC(CC#N)=C(Br)C=C1

Description

2-(2-Bromo-5-methoxyphenyl)acetonitrile features a brominated aromatic ring paired with a methoxy group and a nitrile-bearing side chain, enabling efficient coupling in cross-coupling reactions. This bench-stable intermediate integrates readily into complex molecular architectures under standard conditions.

Application

2-(2-Bromo-5-methoxyphenyl)acetonitrile serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions to construct biaryl and heteroaryl scaffolds. The bromo group facilitates efficient coupling with boronic acids, while the nitrile and methoxy functionalities offer orthogonal reactivity for downstream transformations. Bench-stable and readily purified by column chromatography, it functions as a key intermediate in the synthesis of functionalized aromatic systems relevant to pharmaceutical and agrochemical development.

Synthesis

  • Route1
    • null|null
      7677-24-9
    • In-stock
      1-Bromo-2-(bromomethyl)-4-methoxybenzene|CS-W008035
      19614-12-1
    • ~94%
    • In-stock
      2-(2-Bromo-5-methoxyphenyl)acetonitrile|CS-0041927
      27387-23-1

    References

    • Chaumontet, Manon; Piccardi, Riccardo; Audic, Nicolas; Hitce, Julien; Peglion, Jean-Louis; Clot, Eric; Baudoin, Olivier Journal of the American Chemical Society, 2008 , vol. 130, # 45 p. 15157 - 15166
  • Route2
    • null|null
      773837-37-9
    • In-stock
      1-Bromo-2-(bromomethyl)-4-methoxybenzene|CS-W008035
      19614-12-1
    • ~%
    • In-stock
      2-(2-Bromo-5-methoxyphenyl)acetonitrile|CS-0041927
      27387-23-1

    References

    • Watanuki, Susumu; Matsuura, Keisuke; Tomura, Yuichi; Okada, Minoru; Okazaki, Toshio; Ohta, Mitsuaki; Tsukamoto, Shin-Ichi Chemical and Pharmaceutical Bulletin, 2011 , vol. 59, # 8 p. 1029 - 1037
  • Route3

    References

    • Kukosha, Tatyana; Trufilkina, Nadezhda; Katkevics, Martins Synlett, 2011 , # 17 p. 2525 - 2528

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   33.02
  • LogP   2.52378
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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