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
Rating: 5 (1 reviews)

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
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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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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

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.

Synthesis

Route1
- In-stock
  
  24424-99-5
- In-stock
  
  4887-88-1
- ~95%
- In-stock
  
  942590-05-8
References
- Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng Patent: US2013/102595 A1, 2013 ; Location in patent: Paragraph 0582 ;
Route2
- In-stock
  
  24424-99-5
- In-stock
  
  4887-88-1
- ~%
- In-stock
  
  942590-05-8
- In-stock
  
  1006899-77-9
References
- ASTRAZENECA AB; ASTRAZENECA UK LIMITED Patent: WO2009/7751 A2, 2009 ; Location in patent: Page/Page column 121 ; WO 2009/007751 A2
Route3
- In-stock
  
  1575-37-7
- ~%
- In-stock
  
  942590-05-8
References
- CURIS, INC.; BAO, Rudi; LAI, Chengjung; QIAN, Changgeng Patent: WO2011/130628 A1, 2011 ; WO 2011/130628 A1

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-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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Computational Chemistry Data

TPSA 44.12
LogP 3.582
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

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

CAS No. 942590-05-8

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