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(S)-Methyl 2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate

  • CAS No. 2230200-76-5

  • Cat. No. CS-0098399
  • Molecule weight294.74
  • Purity≥98%
  • MDL No.MFCD32068480

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

(S)-Methyl 2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate|CS-0098399

Structure of 2230200-76-5

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General Information

  • CAS No. 2230200-76-5
  • Cat. No. CS-0098399
  • Purity ≥98%
  • MDL No. MFCD32068480
  • Storage 4°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₅ClN₂O₃
  • Molecular Weight 294.74
  • Synonym(s) methyl 2-(chloromethyl)-3-[[(2S)-oxetan-2-yl]methyl]benzimidazole-5-carboxylate
  • SMILES O=C(OC)C1=CC=C2N=C(N(C2=C1)C[C@H]3OCC3)CCl

Description

(S)-Methyl 2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate features a chiral oxetane-bearing side chain that enhances membrane permeability and metabolic stability. The chloromethyl group enables site-specific functionalization, while the benzoimidazole core provides a rigid, electron-deficient scaffold ideal for medicinal chemistry applications. This compound serves as a key building block in the synthesis of targeted covalent inhibitors.

Application

(S)-Methyl 2-(chloromethyl)-1-(oxetan-2-ylmethyl)-1H-benzo[d]imidazole-6-carboxylate serves as a versatile synthetic intermediate for constructing bioactive heterocycles. The chloromethyl group enables efficient nucleophilic substitution, while the oxetane ring imparts metabolic stability and favorable physicochemical properties. This scaffold facilitates rapid diversification in medicinal chemistry campaigns, particularly in kinase inhibitor and CNS-targeted compound development. Its bench-stable nature and compatibility with standard coupling protocols support scalable synthesis and purification.

Safety Information

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GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3261
Class : 8
Packing Group : Ⅱ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   2.3506
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   4

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