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CS-W001157 4
Total: USD 88.00

3-(2-Cyanopropan-2-yl)benzoic acid

  • CAS No. 872091-00-4

  • Cat. No. CS-W009132
  • Purity≥97%
  • MDL No.MFCD19694856

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

3-(2-Cyanopropan-2-yl)benzoic acid|CS-W009132

Structure of 872091-00-4

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General Information

  • CAS No. 872091-00-4
  • Cat. No. CS-W009132
  • Purity ≥97%
  • MDL No. MFCD19694856
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₁NO₂
  • Molecular Weight 189.21
  • Synonym(s) 3-(2-Cyano-2-propanyl)benzoic acid
  • SMILES O=C(O)C1=CC=CC(C(C)(C#N)C)=C1

Description

This benzoic acid derivative features a sterically hindered nitrile group at the 3-position, enhancing metabolic stability and enabling direct incorporation into bioactive scaffolds. The para-cyanopropyl substituent imparts electron-withdrawing character, modulating reactivity in coupling reactions and facilitating downstream functionalization in medicinal chemistry applications.

Application

3-(2-Cyanopropan-2-yl)benzoic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of functionalized benzene derivatives through standard coupling and transformation protocols. Its nitrile group offers high stability and compatibility with diverse reaction conditions, while the tert-butyl-like steric bulk enhances metabolic resistance in target scaffolds. The carboxylic acid functionality facilitates direct amidation or esterification, supporting rapid diversification in lead optimization campaigns.

Synthesis

  • Route1
    • Methyl 3-(2-cyanopropan-2-yl)benzoate|CS-0199251
      872091-85-5
    • ~99%
    • In-stock
      3-(2-Cyanopropan-2-yl)benzoic acid|CS-W009132
      872091-00-4

    References

    • Galemmo, JR., Robert; Holland, Richard; Hum, Gabriel; Pajouhesh, Hossein; Chahal, Navjot; Seid-Bagherzadeh, Mehran; Girard, Amy Patent: US2009/270394 A1, 2009 ; Location in patent: Page/Page column 12 ; US 20090270394 A1
  • Route2
    • Ethyl 3-(2-cyanopropan-2-yl)benzoate|CS-0683804
      1012342-24-3
    • ~%
    • In-stock
      3-(2-Cyanopropan-2-yl)benzoic acid|CS-W009132
      872091-00-4

    References

    • WO2008/28617 A1, ; Page/Page column 46 ; WO 2008/028617 A1

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   61.09
  • LogP   2.18598
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   2

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