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CS-W001157 4
Total: USD 88.00

2-(Chloromethyl)-2-methyloxirane

  • CAS No. 598-09-4

  • Cat. No. CS-0089843
  • Purity≥98%
  • MDL No.MFCD00052487

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

2-(Chloromethyl)-2-methyloxirane|CS-0089843

Structure of 598-09-4

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General Information

  • CAS No. 598-09-4
  • Cat. No. CS-0089843
  • Purity ≥98%
  • MDL No. MFCD00052487
  • Storage -20°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₇ClO
  • Molecular Weight 106.55
  • Synonym(s) Methyl epichlorohydrin; 2-(Chloromethyl)-2-methyloxirane
  • SMILES ClCC1(C)CO1

Description

2-(Chloromethyl)-2-methyloxirane is a strained epoxide featuring a reactive chloromethyl group, enabling selective functionalization in synthetic workflows. This bifunctional scaffold integrates seamlessly into complex molecular architectures, offering high chemoselectivity under mild conditions. The molecule exhibits enhanced stability compared to standard halogenated epoxides, facilitating handling and storage without significant decomposition.

Application

2-(Chloromethyl)-2-methyloxirane serves as a versatile bifunctional building block, enabling efficient ring-opening reactions with nucleophiles under mild conditions. Its strained oxirane ring exhibits high reactivity toward amines, thiols, and carboxylates, while the pendant chloromethyl group permits further functionalization via SN2 displacement. This dual functionality facilitates the synthesis of complex heterocycles and side-chain elaborations in medicinal chemistry workflows. The compound demonstrates good bench stability and is amenable to standard purification protocols.

Synthesis

  • Route1
    • null|null
      563-47-3
    • ~46%
    • In-stock
      2-(Chloromethyl)-2-methyloxirane|CS-0089843
      598-09-4

    References

    • Terranova, Eric; Fadli, Aziz Patent: US2003/28976 A1, 2003 ;
  • Route2
    • null|null
      597-32-0
    • ~72%
    • In-stock
      2-(Chloromethyl)-2-methyloxirane|CS-0089843
      598-09-4

    References

    • Galons; Combet Farnoux; Miocque; et al. European Journal of Medicinal Chemistry, 1984 , vol. 19, # 1 p. 23 - 27
  • Route3
    • null|null
      66466-56-6
    • ~82%
    • In-stock
      2-(Chloromethyl)-2-methyloxirane|CS-0089843
      598-09-4

    References

    • Pugia, Michael; Knudsen, Brian E.; Cason, C. Victor; Bartsch, Richard A. Journal of Organic Chemistry, 1987 , vol. 52, # 4 p. 541 - 547

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS05
Signal Word : Danger
UN#: 2920
Class : 8,3
Packing Group : Ⅱ
Hazard Statements : H225-H314
Precautionary Statements : P210-P233-P240-P241-P242-P243-P260-P264-P280-P301+P330+P331-P304+P340-P363-P370+P378-P405-P501

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Computational Chemistry Data

  • TPSA   12.53
  • LogP   1.0141
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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