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CS-W001157 4
Total: USD 88.00

5-Bromo-2,3-dihydrobenzofuran

  • CAS No. 66826-78-6

  • Cat. No. CS-W004134
  • Purity≥98%
  • MDL No.MFCD02677716

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

5-Bromo-2,3-dihydrobenzofuran|CS-W004134

Structure of 66826-78-6

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General Information

  • CAS No. 66826-78-6
  • Cat. No. CS-W004134
  • Purity ≥98%
  • MDL No. MFCD02677716
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇BrO
  • Molecular Weight 199.04
  • Synonym(s) 5-Bromocoumaran
  • SMILES BrC1=CC=C(OCC2)C2=C1

Description

5-Bromo-2,3-dihydrobenzofuran is a bench-stable heterocyclic scaffold featuring a bromine substituent at the 5-position and a saturated furan ring. This configuration enables direct functionalization in cross-coupling reactions and provides enhanced solubility over aromatic analogs. The compound serves as a key building block in medicinal chemistry and materials science.

Application

5-Bromo-2,3-dihydrobenzofuran serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable aryl bromide functionality. The dihydrobenzofuran core provides structural rigidity and metabolic stability, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1

    References

    • Matsunaga, Nobuyuki; Kaku, Tomohiro; Ojida, Akio; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 16 p. 4313 - 4336
  • Route2

    References

    • Song, Zhiguo J.; Zhao, Matthew; Frey, Lisa; Li, Jing; Tan, Lushi; Chen, Cheng Y.; Tschaen, David M.; Tillyer, Richard; Grabowski, Edward J. J.; Volante, Ralph; Reider, Paul J.; Kato, Yoshiaki; Okada, Shigemitsu; Nemoto, Takayuki; Sato, Hiroki; Akao, Atsushi; Mase, Toshiaki Organic Letters, 2001 , vol. 3, # 21 p. 3357 - 3360
  • Route3
    • 2,4-Dibromo-1-(2-bromoethoxy)benzene|CS-0671590
      76429-66-8
    • ~79%
    • In-stock
      5-Bromo-2,3-dihydrobenzofuran|CS-W004134
      66826-78-6

    References

    • Bradsher, Charles K.; Reames, David C. Journal of Organic Chemistry, 1981 , vol. 46, # 7 p. 1384 - 1388

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   9.23
  • LogP   2.384
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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