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CS-W001157 4
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6-(Dimethylamino)-2-naphthalenecarboxaldehyde

  • CAS No. 173471-71-1

  • Cat. No. CS-0018968
  • Purity≥98%
  • MDL No.MFCD07776686

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

6-(Dimethylamino)-2-naphthalenecarboxaldehyde|CS-0018968

Structure of 173471-71-1

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General Information

  • CAS No. 173471-71-1
  • Cat. No. CS-0018968
  • Purity ≥98%
  • MDL No. MFCD07776686
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₃NO
  • Molecular Weight 199.25
  • Synonym(s) 6-(Dimethylamino)-2-naphthaldehyde; 6-Dimethylamino-2-naphthalenecarboxaldehyde; 6-DIMETHYLAMINO-2-NAPHTHALDEHYDE
  • SMILES O=CC1=CC=C2C=C(N(C)C)C=CC2=C1

Description

6-(Dimethylamino)-2-naphthalenecarboxaldehyde features a conjugated naphthalene core with an electron-rich dimethylamino group and a reactive aldehyde function. This combination enables efficient coupling in condensation reactions, particularly in the synthesis of fluorescent probes and Schiff base architectures. The compound exhibits enhanced solubility in organic solvents and stability under standard bench conditions.

Application

6-(Dimethylamino)-2-naphthalenecarboxaldehyde serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized naphthalene scaffolds. Its aldehyde functionality facilitates nucleophilic additions, condensations, and reductive aminations, while the electron-donating dimethylamino group enhances reactivity at the C-6 position. The compound exhibits good bench stability and is compatible with common protecting group strategies, making it suitable for iterative synthesis and library generation in medicinal chemistry workflows.

Synthesis

  • Route1
    • (6-(Dimethylamino)naphthalen-2-yl)methanol|CS-0677191
      891491-99-9
    • ~72%
    • In-stock
      6-(Dimethylamino)-2-naphthalenecarboxaldehyde|CS-0018968
      173471-71-1

    References

    • KYOTO UNIVERSITY; NIHON UNIVERSITY; OTSUKA PHARMACEUTICAL CO., LTD. Patent: US2006/142311 A1, 2006 ; Location in patent: Page/Page column 18; sheet 2 ;
  • Route2
    • In-stock
      6-Bromo-N,N-dimethylnaphthalen-2-amine|CS-0465694
      5043-03-8
    • null|null
      68-12-2
    • ~86%
    • In-stock
      6-(Dimethylamino)-2-naphthalenecarboxaldehyde|CS-0018968
      173471-71-1

    References

    • Rao, Alla Sreenivasa; Kim, Dokyoung; Wang, Taejun; Kim, Ki Hean; Hwang, Sekyu; Ahn, Kyo Han Organic Letters, 2012 , vol. 14, # 10 p. 2598 - 2601
  • Route3

    References

    • Organic Letters, , vol. 14, # 10 p. 2598 - 2601

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   20.31
  • LogP   2.7183
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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