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CS-W001157 4
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tert-Butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate

  • CAS No. 412348-27-7

  • Cat. No. CS-0132712
  • Molecule weight342.23
  • Purity≥97%
  • MDL No.MFCD11872605

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

tert-Butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate|CS-0132712

Structure of 412348-27-7

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General Information

  • CAS No. 412348-27-7
  • Cat. No. CS-0132712
  • Purity ≥97%
  • MDL No. MFCD11872605
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₀BrN₃O₂
  • Molecular Weight 342.23
  • Synonym(s) ert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate
  • SMILES O=C(N1CCN(C2=CN=C(Br)C=C2)CC1)OC(C)(C)C

Description

tert-Butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate features a brominated pyridine moiety appended to a piperazine core, enabling direct integration into cross-coupling reactions. The tert-butyl carbamate group offers stability and convenient deprotection under mild acidic conditions. This compound serves as a key intermediate in the synthesis of bioactive molecules, particularly in medicinal chemistry campaigns targeting kinase inhibitors and CNS-active compounds.

Application

tert-Butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate serves as a versatile building block in medicinal chemistry, enabling efficient late-stage functionalization via palladium-catalyzed cross-coupling reactions. The bromopyridine moiety facilitates Suzuki, Stille, and Negishi couplings, while the piperazine scaffold provides a polar, basic nitrogen for hydrogen bonding and solubility enhancement. The tert-butyl carbamate group offers stability during storage and purification, and can be selectively removed under mild acidic conditions to reveal the free piperazine amine. This compound exhibits excellent bench stability, compatibility with diverse reaction conditions, and predictable reactivity in standard synthetic workflows.

Synthesis

  • Route1

    References

    • Audouze, Karine; Nielsen, Elsebet stergaard; Olsen, Gunnar M.; Ahring, Philip; Jorgensen, Tino Dyhring; Peters, Dan; Liljefors, Tommy; Balle, Thomas Journal of Medicinal Chemistry, 2006 , vol. 49, # 11 p. 3159 - 3171
  • Route2

    References

    • Audouze, Karine; Nielsen, Elsebet stergaard; Olsen, Gunnar M.; Ahring, Philip; Jorgensen, Tino Dyhring; Peters, Dan; Liljefors, Tommy; Balle, Thomas Journal of Medicinal Chemistry, 2006 , vol. 49, # 11 p. 3159 - 3171
  • Route3

    References

    • Audouze, Karine; Nielsen, Elsebet stergaard; Olsen, Gunnar M.; Ahring, Philip; Jorgensen, Tino Dyhring; Peters, Dan; Liljefors, Tommy; Balle, Thomas Journal of Medicinal Chemistry, 2006 , vol. 49, # 11 p. 3159 - 3171

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

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Computational Chemistry Data

  • TPSA   45.67
  • LogP   2.9012
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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