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CS-W001157 4
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2-(Bromomethyl)acrylic acid

  • CAS No. 72707-66-5

  • Cat. No. CS-W017896
  • Purity≥95%
  • MDL No.MFCD00004259

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

2-(Bromomethyl)acrylic acid|CS-W017896

Structure of 72707-66-5

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General Information

  • CAS No. 72707-66-5
  • Cat. No. CS-W017896
  • Purity ≥95%
  • MDL No. MFCD00004259
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₄H₅BrO₂
  • Molecular Weight 164.99
  • Synonym(s) α-(Bromomethyl)acrylic acid; α-Methylated acrylamide; α-MAA
  • SMILES C=C(C(O)=O)CBr

Description

Reacts with aldehydes and ketones to form -methylene-butyrolactones. Used in the synthesis of methotrexate analogues.

Application

2-(Bromomethyl)acrylic acid serves as a versatile bifunctional building block, enabling efficient conjugate additions and Michael-type reactions. The bromomethyl group facilitates nucleophilic substitution, while the acrylic acid moiety supports copolymerization or further functionalization via its α,β-unsaturated system. Its bench-stable nature and compatibility with diverse reaction conditions make it valuable for synthesizing bioactive intermediates and polymerizable monomers in medicinal chemistry and materials science workflows.

Synthesis

  • Route1

    References

    • Sun, Chong-Si; Cheng, Hsiu-Yi; Lin, Yu-Shiang; Hou, Duen-Ren Journal of the Chinese Chemical Society, 2008 , vol. 55, # 2 p. 435 - 438
  • Route2
    • null|null
      79-41-4
    • ~75%
    • In-stock
      2-(Bromomethyl)acrylic acid|CS-W017896
      72707-66-5

    References

    • Khazaei, Ardeshir; Vaghei, Ramin Ghorbani; Karkhanei, Ebrahim Synthetic Communications, 2002 , vol. 32, # 14 p. 2107 - 2113
  • Route3

    References

    • Hoefling, Sarah B.; Hultsch, Christina; Wester, Hans-Juergen; Heinrich, Markus R. Tetrahedron, 2008 , vol. 64, # 52 p. 11846 - 11851

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   1.0221
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   2

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