(1R,3S,4S)-tert-Butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

Name: (1R,3S,4S)-tert-Butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 1256387-74-2
Cat. No. CS-M3715
Purity≥98%
MDL No.MFCD28386937

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(1R,3S,4S)-tert-Butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate|CS-M3715

Structure of 1256387-74-2

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Description

This bicyclic scaffold features a sterically defined azabicyclo[2.2.1]heptane core bearing a tert-butyl ester and a brominated benzoimidazole moiety, enabling direct incorporation into complex heterocyclic systems. The configuration at the 1R,3S,4S centers ensures predictable stereochemical control in downstream transformations.

Application

(1R,3S,4S)-tert-Butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate serves as a versatile chiral building block for the synthesis of bioactive heterocycles. The bromo-substituted benzoimidazole moiety enables palladium-catalyzed cross-coupling reactions, while the bicyclic azabridge provides conformational rigidity and enhanced metabolic stability. Its tert-butyl ester facilitates straightforward deprotection and functionalization, making it ideal for medicinal chemistry campaigns requiring robust, stereocontrolled scaffolds.

General Information

CAS No. 1256387-74-2
Cat. No. CS-M3715
Purity ≥98%
MDL No. MFCD28386937
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₂BrN₃O₂
Molecular Weight None
Synonym(s) (1R,3S,4S)-3-(6-BroMo-1H-benziMidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1,1-diMethylethyl ester
SMILES O=C(N1[C@](C2)([H])CC[C@]2([H])[C@H]1C3=NC4=CC=C(Br)C=C4N3)OC(C)(C)C

Computational Chemistry Data

TPSA 58.22
LogP 4.7859
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302
Precautionary Statements : P264-P270-P301+P310-P330-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperidine compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Key Words

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(1R,3S,4S)-tert-Butyl 3-(6-bromo-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

CAS No. 1256387-74-2

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