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CS-W001157 4
Total: USD 88.00

2-Methoxy-6-nitrobenzaldehyde

  • CAS No. 19689-88-4

  • Cat. No. CS-0133796
  • Purity≥97%
  • MDL No.MFCD07371505

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

2-Methoxy-6-nitrobenzaldehyde|CS-0133796

Structure of 19689-88-4

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General Information

  • CAS No. 19689-88-4
  • Cat. No. CS-0133796
  • Purity ≥97%
  • MDL No. MFCD07371505
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₄
  • Molecular Weight 181.15
  • Synonym(s) 6-Methoxy-2-nitrobenzaldehyde,2-Methoxy-6-nitrobenzaldehyde
  • SMILES O=CC1=C([N+]([O-])=O)C=CC=C1OC

Description

2-Methoxy-6-nitrobenzaldehyde features a nitro group positioned ortho to the aldehyde, enhancing electrophilicity for efficient coupling reactions. The methoxy substituent provides electron-donating character and improved solubility in organic solvents. This combination enables selective functionalization in synthetic routes requiring activated aromatic aldehydes.

Application

2-Methoxy-6-nitrobenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to substituted heterocycles and functionalized aromatic scaffolds. Its ortho-directed reactivity, combined with the complementary electronic effects of the methoxy and nitro groups, facilitates regioselective transformations. The aldehyde functionality supports standard condensation reactions, while the nitro group allows for controlled reduction or further functionalization. Bench-stable and readily purified by recrystallization, it functions effectively in multistep syntheses requiring precise substitution patterns.

Synthesis

  • Route1

    References

    • Journal of Organic Chemistry, , vol. 24, p. 866
  • Route2

    References

    • Journal of Fluorine Chemistry, , vol. 128, # 12 p. 1461 - 1468
  • Route3
    • (2-Methoxy-6-nitrophenyl)methanol|CS-0336605
      19689-87-3
    • ~%
    • In-stock
      2-Methoxy-6-nitrobenzaldehyde|CS-0133796
      19689-88-4

    References

    • Journal of Organic Chemistry, , vol. 34, # 5 p. 1364 - 1367

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363

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Computational Chemistry Data

  • TPSA   69.44
  • LogP   1.4159
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   3

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