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tert-Butyl 3-bromopropanoate

  • CAS No. 55666-43-8

  • Cat. No. CS-W022995
  • Purity≥98%
  • MDL No.MFCD04974087

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

tert-Butyl 3-bromopropanoate|CS-W022995

Structure of 55666-43-8

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General Information

  • CAS No. 55666-43-8
  • Cat. No. CS-W022995
  • Purity ≥98%
  • MDL No. MFCD04974087
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₃BrO₂
  • Molecular Weight 209.08
  • Synonym(s) None
  • SMILES O=C(OC(C)(C)C)CCBr

Description

tert-Butyl 3-bromopropanoate features a brominated aliphatic chain tethered to a sterically hindered tert-butyl ester, enabling stable incorporation into synthetic sequences. This combination delivers enhanced resistance to hydrolysis and facilitates selective functionalization in multistep organic transformations.

Application

tert-Butyl 3-bromopropanoate serves as a versatile bifunctional building block in synthetic organic chemistry, enabling efficient access to γ-bromocarboxylate derivatives. Its bromide functionality facilitates nucleophilic substitution and transition-metal-catalyzed coupling reactions, while the tert-butyl ester group offers stability and convenient deprotection under mild acidic conditions. This combination supports robust functionalization in complex molecule synthesis, particularly for heterocyclic scaffolds and pharmaceutical intermediates requiring orthogonal reactivity.

Synthesis

  • Route1

    References

    • BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; BETAGERI, Rajashekhar; RIETHER, Doris; HICKEY, Eugene Richard; WU, Lifen; ZINDELL, Renee M.; KHOR, Someina Patent: WO2010/77836 A2, 2010 ; Location in patent: Page/Page column 129 ; WO 2010/077836 A2
  • Route2
    • null|null
      590-92-1
    • null|null
      115-11-7
    • ~%
    • In-stock
      tert-Butyl 3-bromopropanoate|CS-W022995
      55666-43-8

    References

    • Pavlov,S. et al. Bulletin de la Societe Chimique de France, 1974 , p. 2985 - 2986
  • Route3
    • null|null
      590-92-1
    • null|null
      75-65-0
    • ~35%
    • In-stock
      tert-Butyl 3-bromopropanoate|CS-W022995
      55666-43-8

    References

    • Jaszberenyi, Zoltan; Sour, Angelique; Toth, Eva; Benmelouka, Meriem; Merbach, Andre E. Dalton Transactions, 2005 , # 16 p. 2713 - 2719

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H227-H302-H315-H319-H335
Precautionary Statements : P210-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P370+P378-P403-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   26.3
  • LogP   2.1131
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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