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CS-W001157 4
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4-Amino-3-hydroxybenzonitrile

  • CAS No. 55586-26-0

  • Cat. No. CS-0039880
  • Purity≥96%
  • MDL No.MFCD06657033

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

4-Amino-3-hydroxybenzonitrile|CS-0039880

Structure of 55586-26-0

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General Information

  • CAS No. 55586-26-0
  • Cat. No. CS-0039880
  • Purity ≥96%
  • MDL No. MFCD06657033
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆N₂O
  • Molecular Weight None
  • Synonym(s) 4-AMINO-3-HYDROXY-BENZONITRILE
  • SMILES N#CC1=CC=C(N)C(O)=C1

Description

4-Amino-3-hydroxybenzonitrile features a strategically positioned amino group and hydroxyl moiety flanking a nitrile-bearing aromatic ring, enabling dual functionalization in synthetic sequences. This electron-rich scaffold facilitates coupling reactions under mild conditions, while the hydroxyl group offers a handle for derivatization or metal chelation. The compound exhibits bench-stable behavior and solubility in common organic solvents, supporting its use in medicinal chemistry and materials synthesis workflows.

Application

4-Amino-3-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling the construction of heterocyclic scaffolds through regioselective functionalization. The ortho-dihydroxy-amino substitution pattern provides multiple handles for derivatization, while the nitrile group offers compatibility with standard coupling and cyclization protocols. Bench-stable and readily purified by recrystallization, it functions effectively in multi-step syntheses requiring precise control over substitution patterns.

Synthesis

  • Route1

    References

    • Widdowson, Katherine L.; Elliott, John D.; Veber, Daniel F.; Nie, Hong; Rutledge, Melvin C.; McCleland, Brent W.; Xiang, Jia-Ning; Jurewicz, Anthony J.; Hertzberg, Robert P.; Foley, James J.; Griswold, Don E.; Martin, Lenox; Lee, Judithann M.; White, John R.; Sarau, Henry M. Journal of Medicinal Chemistry, 2004 , vol. 47, # 6 p. 1319 - 1321
  • Route2

    References

    • SmithKline Beecham Corporation Patent: US6262113 B1, 2001 ; US 6262113 B1
  • Route3

    References

    • Varchi, Greta; Kofink, Christiane; Lindsay, David M.; Ricci, Alfredo; Knochel, Paul Chemical Communications, 2003 , # 3 p. 396 - 397

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: 3439
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H312-H315-H319-H332-H335
Precautionary Statements : P260-P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P304+P341-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   70.04
  • LogP   0.84608
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   0

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