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CS-W001157 4
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2-(Chloromethyl)quinazolin-4(3H)-one

  • CAS No. 3817-05-8

  • Cat. No. CS-0033849
  • Purity≥95%
  • MDL No.MFCD01927196

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

2-(Chloromethyl)quinazolin-4(3H)-one|CS-0033849

Structure of 3817-05-8

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General Information

  • CAS No. 3817-05-8
  • Cat. No. CS-0033849
  • Purity ≥95%
  • MDL No. MFCD01927196
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇ClN₂O
  • Molecular Weight 194.62
  • Synonym(s) 2-Chloromethyl-4-(3H)-quinozolinone
  • SMILES O=C1NC(CCl)=NC2=C1C=CC=C2

Description

2-(Chloromethyl)quinazolin-4(3H)-one features a reactive chloromethyl group attached to the quinazolinone scaffold, enabling site-specific conjugation in medicinal chemistry. This electrophilic handle facilitates efficient coupling with nucleophiles, including amines and thiols, under mild conditions. The molecule exhibits excellent bench stability and solubility in common organic solvents, streamlining integration into synthetic workflows for targeted probe development and drug discovery applications.

Application

2-(Chloromethyl)quinazolin-4(3H)-one serves as a versatile building block for medicinal chemistry and heterocyclic synthesis, enabling efficient C–C and C–N bond formation via nucleophilic substitution. The chloromethyl group exhibits high reactivity toward amines, thiols, and carbon nucleophiles under mild conditions, facilitating rapid diversification of the quinazolinone scaffold. Its bench-stable nature and compatibility with common functional groups make it ideal for parallel library synthesis and API development workflows.

Synthesis

  • Route1
    • null|null
      107-14-2
    • null|null
      134-20-3
    • ~82%
    • In-stock
      2-(Chloromethyl)quinazolin-4(3H)-one|CS-0033849
      3817-05-8

    References

    • MYRIAD GENETICS, INC.; CYTOVIA, INC. Patent: WO2006/74187 A2, 2006 ; Location in patent: Page/Page column 54 ; WO 2006/074187 A2
  • Route2
    • null|null
      107-14-2
    • null|null
      87-25-2
    • ~95%
    • In-stock
      2-(Chloromethyl)quinazolin-4(3H)-one|CS-0033849
      3817-05-8

    References

    • Jain, Kishor S.; Bariwal, Jitender B.; Phoujdar, Manisha S.; Nagras, Madhuri A.; Amrutkar, Rakesh D.; Munde, Manoj K.; Tamboli, Riyaj S.; Khedkar, Samrat A.; Khiste, Rahul H.; Vidyasagar, Nikhil C.; Dabholkar, Vinit V.; Kathiravan Journal of Heterocyclic Chemistry, 2009 , vol. 46, # 2 p. 178 - 185
  • Route3
    • 2-[(Chloroacetyl)amino]benzamide|CS-0206083
      21721-78-8
    • ~85%
    • In-stock
      2-(Chloromethyl)quinazolin-4(3H)-one|CS-0033849
      3817-05-8

    References

    • Kabri, Youssef; Gellis, Armand; Vanelle, Patrice European Journal of Organic Chemistry, 2009 , # 24 p. 4059 - 4066

Safety Information

Download SDS
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-P363-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   45.75
  • LogP   1.6619
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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