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tert-Butyl 6-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

  • CAS No. 622867-53-2

  • Cat. No. CS-0214366
  • Purity≥97%
  • MDL No.MFCD12408125

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

tert-Butyl 6-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate|CS-0214366

Structure of 622867-53-2

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General Information

  • CAS No. 622867-53-2
  • Cat. No. CS-0214366
  • Purity ≥97%
  • MDL No. MFCD12408125
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₀BrNO₂
  • Molecular Weight 326.23
  • Synonym(s) tert-butyl 6-(bromomethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
  • SMILES O=C(N1CC2=C(C=C(CBr)C=C2)CC1)OC(C)(C)C

Description

tert-Butyl 6-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate features a bromomethyl group at the 6-position of a dihydroisoquinoline scaffold, enabling facile functionalization in late-stage diversification. The tert-butyl ester offers enhanced stability and ease of handling under standard conditions. This building block integrates efficiently into synthetic sequences requiring selective alkylation or transition-metal-catalyzed coupling reactions.

Application

tert-Butyl 6-(bromomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate serves as a versatile synthetic intermediate for constructing isoquinoline-based scaffolds. The bromomethyl group enables efficient nucleophilic substitution reactions, facilitating the installation of diverse side chains under mild conditions. Its bench-stable tert-butyl carbamate protecting group offers excellent functional group tolerance and simplifies purification. This reagent is particularly valuable in medicinal chemistry campaigns requiring rapid diversification of dihydroisoquinoline cores.

Safety Information

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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-P330-P363-P405-P501

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Computational Chemistry Data

  • TPSA   29.54
  • LogP   3.8747
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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