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CS-W001157 4
Total: USD 88.00

4-Methylenetetrahydro-2H-pyran

  • CAS No. 36838-71-8

  • Cat. No. CS-W004277
  • Purity≥98%
  • MDL No.MFCD09970801

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

4-Methylenetetrahydro-2H-pyran|CS-W004277

Structure of 36838-71-8

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General Information

  • CAS No. 36838-71-8
  • Cat. No. CS-W004277
  • Purity ≥98%
  • MDL No. MFCD09970801
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₀O
  • Molecular Weight 98.14
  • Synonym(s) 2H-Pyran,tetrahydro-4-methylene
  • SMILES C=C1CCOCC1

Description

4-Methylenetetrahydro-2H-pyran features a reactive exocyclic methylene group flanked by a saturated oxygen-containing ring, enabling efficient cycloadditions and functionalization. This electron-rich heterocycle serves as a key building block in synthetic organic chemistry, particularly for constructing complex carbocyclic and heterocyclic frameworks under mild conditions.

Application

4-Methylenetetrahydro-2H-pyran serves as a versatile synthetic building block for constructing oxygen-containing heterocycles and functionalized intermediates. Its exocyclic alkene enables efficient Michael additions, Diels-Alder reactions, and transition-metal-catalyzed couplings. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and natural product workflows.

Synthesis

  • Route1
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      1779-49-3
    • ~72%
    • In-stock
      4-Methylenetetrahydro-2H-pyran|CS-W004277
      36838-71-8

    References

    • Kabat, Marek M.; Lange, Meinolf; Wovkulich, Peter M.; Uskokovic, Milan R. Tetrahedron Letters, 1992 , vol. 33, # 50 p. 7701 - 7704
  • Route2

    References

    • BASF Aktiengesellschaft Patent: US5001242 A1, 1991 ;
  • Route3
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      19493-09-5
    • ~60%
    • In-stock
      4-Methylenetetrahydro-2H-pyran|CS-W004277
      36838-71-8

    References

    • Margot, Christian; Rizzolio, Michele; Schlosser, Manfred Tetrahedron, 1990 , vol. 46, # 7 p. 2411 - 2424

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H225-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   1.353
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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