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CS-W001157 4
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N-Benzyl-2-chloroacetamide

  • CAS No. 2564-06-9

  • Cat. No. CS-0033864
  • Purity≥97%
  • MDL No.MFCD00084929

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

N-Benzyl-2-chloroacetamide|CS-0033864

Structure of 2564-06-9

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General Information

  • CAS No. 2564-06-9
  • Cat. No. CS-0033864
  • Purity ≥97%
  • MDL No. MFCD00084929
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₀ClNO
  • Molecular Weight 183.63
  • Synonym(s) N-Benzylchloroacetamide; NSC 60743; 2-Chloro-N-benzylacetamide
  • SMILES O=C(NCC1=CC=CC=C1)CCl

Description

N-Benzyl-2-chloroacetamide delivers a reactive chloroacetyl moiety coupled with a benzyl-amide handle, enabling efficient conjugation in bioconjugation workflows. This bench-stable reagent integrates readily into peptide and small-molecule scaffolds under mild conditions, offering selective acylation through nucleophilic substitution.

Application

N-Benzyl-2-chloroacetamide serves as a versatile building block in synthetic organic chemistry, enabling the efficient construction of heterocyclic scaffolds through cyclization reactions. Its chloroacetamide functionality exhibits high reactivity in nucleophilic substitution processes, particularly under mild conditions, and demonstrates excellent bench stability and ease of purification. The benzyl group provides steric and electronic modulation while enhancing solubility in common organic solvents, making it well-suited for use in medicinal chemistry campaigns and process-scale synthesis.

Synthesis

  • Route1
    • null|null
      79-04-9
    • null|null
      100-46-9
    • ~99%
    • In-stock
      N-Benzyl-2-chloroacetamide|CS-0033864
      2564-06-9

    References

    • Cho, Su-Dong; Song, Sang-Yong; Park, Yong-Dae; Kim, Jeum-Jong; Joo, Woo-Hong; Shiro, Motoo; Falck; Shin, Dong-Soo; Yoon, Yong-Jin Tetrahedron Letters, 2003 , vol. 44, # 50 p. 8995 - 8998
  • Route2
    • null|null
      105-39-5
    • null|null
      100-46-9
    • ~92%
    • In-stock
      N-Benzyl-2-chloroacetamide|CS-0033864
      2564-06-9

    References

    • Morimoto, Hiroyuki; Fujiwara, Risa; Shimizu, Yuhei; Morisaki, Kazuhiro; Ohshima, Takashi Organic Letters, 2014 , vol. 16, # 7 p. 2018 - 2021
  • Route3
    • null|null
      107-14-2
    • In-stock
      Benzyl alcohol|CS-4355
      100-51-6
    • ~99%
    • In-stock
      N-Benzyl-2-chloroacetamide|CS-0033864
      2564-06-9

    References

    • Salehi; Khodaei; Zolfigol; Keyvan Synthetic Communications, 2001 , vol. 31, # 13 p. 1947 - 1951

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   29.1
  • LogP   1.5416
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   3

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