tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate

Name: tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate
Brand: ChemScene
Availability: InStock
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CAS No. 942590-05-8
Cat. No. CS-0096061
Purity≥97%
MDL No.MFCD13182500

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate|CS-0096061

Structure of 942590-05-8

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Description

tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate features a brominated benzoimidazole core with a bench-stable tert-butyl ester handle, enabling direct use in cross-coupling reactions. The electron-deficient aromatic system facilitates palladium-catalyzed transformations, while the protected carboxylate simplifies purification and functionalization in synthetic sequences.

Application

tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate serves as a versatile building block for the synthesis of brominated benzimidazole scaffolds, enabling palladium-catalyzed cross-coupling reactions. The tert-butyl carbamate group provides stability and ease of removal under mild acidic conditions, while the bromine substituent offers high reactivity in Suzuki, Stille, and Negishi couplings. This compound exhibits excellent bench stability and compatibility with diverse functional groups, facilitating efficient access to complex heterocyclic architectures in medicinal chemistry and materials science applications.

General Information

CAS No. 942590-05-8
Cat. No. CS-0096061
Purity ≥97%
MDL No. MFCD13182500
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₃BrN₂O₂
Molecular Weight 297.15
Synonym(s) 2-Methyl-2-propanyl 5-bromo-1H-benzimidazole-1-carboxylate
SMILES O=C(N1C2=CC=C(Br)C=C2N=C1)OC(C)(C)C

Computational Chemistry Data

TPSA 44.12
LogP 3.582
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Key Words

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tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate

CAS No. 942590-05-8

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