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CS-W001157 4
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2-Chloro-3-hydroxybenzonitrile

  • CAS No. 51786-11-9

  • Cat. No. CS-W021640
  • Molecule weight153.57
  • Purity≥97%
  • MDL No.MFCD11848763

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

2-Chloro-3-hydroxybenzonitrile|CS-W021640

Structure of 51786-11-9

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General Information

  • CAS No. 51786-11-9
  • Cat. No. CS-W021640
  • Purity ≥97%
  • MDL No. MFCD11848763
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄ClNO
  • Molecular Weight 153.57
  • Synonym(s) Benzonitrile, 2-chloro-3-hydroxy-
  • SMILES OC1=CC=CC(C#N)=C1Cl

Description

2-Chloro-3-hydroxybenzonitrile features a hydroxyl group ortho to a nitrile, flanked by a chlorine substituent, enabling selective functionalization in heterocyclic synthesis. This electron-deficient aromatic scaffold supports efficient coupling reactions under mild conditions and exhibits enhanced solubility in polar aprotic solvents.

Application

2-Chloro-3-hydroxybenzonitrile serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the hydroxyl and nitrile groups. Its ortho-chloro substituent facilitates subsequent cross-coupling reactions, while the phenolic OH offers sites for derivatization or protection. The molecule exhibits good bench stability and compatibility with standard purification techniques, making it suitable for use in multi-step syntheses of heterocyclic scaffolds and API intermediates.

Synthesis

  • Route1

    References

    • ASTRAZENECA AB; ASTRAZENECA UK LIMITED; BIRCH, Alan, Martin; GOLDBERG, Frederick, Woolf; LEACH, Andrew Patent: WO2011/121350 A1, 2011 ; Location in patent: Page/Page column 105 ; WO 2011/121350 A1
  • Route2

    References

    • Pfizer Inc Patent: US2006/160786 A1, 2006 ; Location in patent: Page/Page column 36 ; US 20060160786 A1
  • Route3

    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

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   44.02
  • LogP   1.91728
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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