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Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate

  • CAS No. 3697-68-5

  • Cat. No. CS-W018860
  • Molecule weight144.17
  • Purity≥95%
  • MDL No.MFCD09759206

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

Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate|CS-W018860

Structure of 3697-68-5

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General Information

  • CAS No. 3697-68-5
  • Cat. No. CS-W018860
  • Purity ≥95%
  • MDL No. MFCD09759206
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₂O₃
  • Molecular Weight 144.17
  • Synonym(s) ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate
  • SMILES CCOC(=O)C1(CO)CC1

Description

Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate features a cyclopropyl ring bearing a hydroxymethyl and ethyl ester group, delivering high stereochemical integrity. This stable, moisture-tolerant reagent integrates readily into asymmetric synthesis workflows, enabling direct functionalization at the cyclopropane core.

Application

Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate serves as a versatile building block in synthetic organic chemistry, enabling the construction of cyclopropyl-containing scaffolds prevalent in medicinal chemistry. The pendant hydroxymethyl group facilitates selective functionalization, while the ester moiety supports standard transformations such as reduction, hydrolysis, and coupling reactions. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthesis workflows and scale-up applications.

Synthesis

  • Route1

    References

    • DOW AGROSCIENCES LLC; Buysse, Ann M.; Niyaz, Noormohamed M.; Demeter, David A.; Zhang, Yu; Walsh, Martin J.; Kubota, Asako; Hunter, Ricky; Trullinger, Tony K.; Lowe, Christian T.; Knueppel, Daniel; Patny, Akshay; Garizi, Negar; LePlae, JR., Paul Renee; Wessels, Frank; Ross, JR., Ronald; DeAmicis, Carl; Borromeo, Peter Patent: US2013/288893 A1, 2013 ; Location in patent: Paragraph 0450-0451 ;
  • Route2

    References

    • SHANGHAI DE NOVO PHARMATECH CO LTD.; GAO, Daxin; YANG, Heping; YU, Yajun Patent: WO2013/91502 A1, 2013 ; Location in patent: Page/Page column 43 ;
  • Route3
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      105-53-3
    • ~%
    • In-stock
      Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate|CS-W018860
      3697-68-5

    References

    • Chang, Xiao-Wei; Han, Qing-Chuan; Jiao, Zhi-Gang; Weng, Lin-Hong; Zhang, Dan-Wei Tetrahedron, 2010 , vol. 66, # 51 p. 9733 - 9737

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   46.53
  • LogP   0.322
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   3

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