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CS-W001157 4
Total: USD 88.00

4-Methyltetrahydro-2H-pyran-4-ol

  • CAS No. 7525-64-6

  • Cat. No. CS-W006621
  • Purity≥97%
  • MDL No.MFCD13193576

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

4-Methyltetrahydro-2H-pyran-4-ol|CS-W006621

Structure of 7525-64-6

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General Information

  • CAS No. 7525-64-6
  • Cat. No. CS-W006621
  • Purity ≥97%
  • MDL No. MFCD13193576
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₁₂O₂
  • Molecular Weight 116.16
  • Synonym(s) 4-Methyltetrahydropyran-4-ol
  • SMILES CC1(CCOCC1)O

Description

4-Methyltetrahydro-2H-pyran-4-ol features a tertiary hydroxyl group flanked by a methyl-substituted tetrahydropyran ring, offering enhanced steric shielding and improved stability. This structural motif enables reliable incorporation into complex synthetic sequences, particularly in carbohydrate mimicry and natural product synthesis. The molecule exhibits favorable solubility in common organic solvents and maintains integrity under standard bench conditions.

Application

4-Methyltetrahydro-2H-pyran-4-ol serves as a versatile chiral building block in synthetic organic chemistry, offering a readily accessible hydroxyl group and a saturated heterocyclic framework. Its bench-stable nature and compatibility with standard protecting group strategies facilitate efficient functionalization. The molecule enables regioselective transformations in complex molecule synthesis, particularly in natural product and medicinal chemistry applications requiring oxygenated tetrahydropyran scaffolds.

Synthesis

  • Route1

    References

    • Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael Patent: US2013/115190 A1, 2013 ; Location in patent: Page/Page column ;
  • Route2
    • In-stock
      Tetrahydro-4H-pyran-4-one|CS-D0601
      29943-42-8
    • null|null
      75-16-1
    • ~%
    • In-stock
      4-Methyltetrahydro-2H-pyran-4-ol|CS-W006621
      7525-64-6

    References

    • WO2005/42533 A2, ; Page/Page column 52 ; WO 2005/042533 A2
  • Route3
    • null|null
      34449-33-7
    • ~62%
    • In-stock
      4-Methyltetrahydro-2H-pyran-4-ol|CS-W006621
      7525-64-6

    References

    • Arakelyan, A. S.; Dvoryanchikov, A. I.; Gevorkyan, A. A. Journal of Organic Chemistry USSR (English Translation), 1987 , vol. 23, # 11 p. 2047 - 2050 Zhurnal Organicheskoi Khimii, 1986 , vol. 23, # 11 p. 2323 - 2326

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   29.46
  • LogP   0.5478
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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