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CS-W001157 4
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Methyl 3-methylidenecyclobutane-1-carboxylate

  • CAS No. 15963-40-3

  • Cat. No. CS-0046881
  • Purity≥98%
  • MDL No.MFCD01087180

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

Methyl 3-methylidenecyclobutane-1-carboxylate|CS-0046881

Structure of 15963-40-3

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General Information

  • CAS No. 15963-40-3
  • Cat. No. CS-0046881
  • Purity ≥98%
  • MDL No. MFCD01087180
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀O₂
  • Molecular Weight 126.15
  • Synonym(s) Methyl 3-methylenecyclobutanecarboxylate
  • SMILES O=C(C1CC(C1)=C)OC

Description

Methyl 3-methylidenecyclobutane-1-carboxylate features a strained cyclobutane core with an exocyclic methylene group, enabling participation in cycloadditions and ring-expansion reactions. This electron-deficient alkene integrates readily into synthetic sequences requiring constrained, reactive intermediates under standard conditions.

Application

Methyl 3-methylidenecyclobutane-1-carboxylate serves as a versatile cyclobutane-based building block for the synthesis of strained ring systems and bioactive scaffolds. Its exocyclic methylene group enables efficient Diels-Alder reactions, Michael additions, and metal-catalyzed cyclizations. The ester functionality offers facile manipulation via hydrolysis or reduction, while the molecule exhibits good bench stability and ease of purification, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • In-stock
      3-Methylenecyclobutanecarboxylic acid|CS-M1233
      15760-36-8
    • null|null
      77-78-1
    • ~86%
    • In-stock
      Methyl 3-methylidenecyclobutane-1-carboxylate|CS-0046881
      15963-40-3

    References

    • ACHAOGEN, INC.; KASAR, Ramesh; LINSELL, Martin Sheringham; AGGEN, James Bradley; LU, Qing (Jane); WANG, Dan; CHURCH, Tim; MOSER, Heinz E.; PATTEN, Phillip A. Patent: WO2012/154204 A1, 2012 ; Location in patent: Page/Page column 67; 68 ;
  • Route2
    • null|null
      67-56-1
    • In-stock
      3-Methylenecyclobutanecarboxylic acid|CS-M1233
      15760-36-8
    • ~%
    • In-stock
      Methyl 3-methylidenecyclobutane-1-carboxylate|CS-0046881
      15963-40-3

    References

    • IRM LLC; TULLY, David C.; RUCKER, Paul Vincent; ALPER, Phillip B.; MUTNICK, Daniel; CHIANELLI, Donatella Patent: WO2012/87519 A1, 2012 ; Location in patent: Page/Page column 104 ; WO 2012/087519 A1
  • Route3
    • 3-Bromomethyl-cyclobutanecarboxylic acid methyl ester|CS-0340660
      89892-95-5
    • ~29%
    • Methyl 3-methylbicyclo[1.1.0]Butane-1-carboxylate|CS-0450756
      30493-92-6
    • In-stock
      Methyl 3-methylidenecyclobutane-1-carboxylate|CS-0046881
      15963-40-3

    References

    • Surmina, L. S.; Zefirov, N. S. Journal of Organic Chemistry USSR (English Translation), 1986 , vol. 22, # 4 p. 777 - 778 Zhurnal Organicheskoi Khimii, 1986 , vol. 22, # 4 p. 870

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H318-H335
Precautionary Statements : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P310-P312-P330-P332+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   1.1256
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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