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CS-W001157 4
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(2E)-3-(1-methylpyrazol-4-yl)prop-2-enoic acid

  • CAS No. 689251-97-6

  • Cat. No. CS-0071358
  • Purity≥98%
  • MDL No.MFCD02090857

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

(2E)-3-(1-methylpyrazol-4-yl)prop-2-enoic acid|CS-0071358

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General Information

  • CAS No. 689251-97-6
  • Cat. No. CS-0071358
  • Purity ≥98%
  • MDL No. MFCD02090857
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈N₂O₂
  • Molecular Weight 152.15
  • Synonym(s) (2E)-3-(1-methyl-1H-pyrazol-4-yl)acrylic acid
  • SMILES O=C(O)/C=C/C1=CN(C)N=C1

Description

This acrylate derivative features a methylpyrazole moiety that enhances solubility and metabolic stability. The (2E)-configured double bond ensures geometric consistency in conjugated systems, enabling reliable incorporation into bioactive scaffolds. Ideal for synthetic applications requiring electron-rich heteroaryl coupling partners.

Application

(2E)-3-(1-methylpyrazol-4-yl)prop-2-enoic acid serves as a versatile building block for heterocyclic and medicinal chemistry applications, offering a conjugated enoic acid moiety that facilitates Michael additions, Diels–Alder reactions, and transition-metal-catalyzed couplings. Its pyrazole functionality provides metabolic stability and hydrogen-bonding capacity, while the (2E)-configuration ensures consistent stereochemical control in downstream transformations. The compound exhibits bench stability and is readily purified by recrystallization or flash chromatography, enabling efficient integration into multi-step syntheses of bioactive scaffolds.

Synthesis

  • Route1
    • In-stock
      1-Methyl-1H-pyrazole-4-carboxaldehyde|CS-W019871
      25016-11-9
    • null|null
      141-82-2
    • ~39%
    • In-stock
      (2E)-3-(1-methylpyrazol-4-yl)prop-2-enoic acid|CS-0071358
      689251-97-6

    References

    • GLAXO GROUP LIMITED; JIN, Yun; WAN, Zehong; ZHANG, Qing Patent: WO2012/76435 A1, 2012 ; Location in patent: Page/Page column 29 ;
  • Route2
    • Methyl (E)-3-(1-methyl-1H-pyrazol-4-yl)acrylate|CS-0571494
      1295583-21-9
    • ~%
    • In-stock
      (2E)-3-(1-methylpyrazol-4-yl)prop-2-enoic acid|CS-0071358
      689251-97-6

    References

    • REPLIGEN CORPORATION; JACQUES, Vincent; RUSCHE, James R.; PEET, Norton P.; SINGH, Jasbir Patent: WO2012/118782 A1, 2012 ; Location in patent: Page/Page column 75 ; WO 2012/118782 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 : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   55.12
  • LogP   0.5179
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   2

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