5-Bromo-1-phenyl-1H-benzo[d]imidazole

Name: 5-Bromo-1-phenyl-1H-benzo[d]imidazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 221636-18-6
Cat. No. CS-0018998
Molecule weight273.13
Purity≥97%
MDL No.MFCD05864728

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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5-Bromo-1-phenyl-1H-benzo[d]imidazole|CS-0018998

Structure of 221636-18-6

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General Information

CAS No. 221636-18-6
Cat. No. CS-0018998
Purity ≥97%
MDL No. MFCD05864728
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₉BrN₂
Molecular Weight 273.13
Synonym(s) 5-Bromo-1-phenyl-1H-benzoimidazole
SMILES BrC1=CC=C2C(N=CN2C3=CC=CC=C3)=C1

Description

5-Bromo-1-phenyl-1H-benzo[d]imidazole features a brominated benzimidazole core paired with a phenyl substituent, delivering enhanced electronic and steric profile for use in cross-coupling reactions. The electron-deficient imidazole ring facilitates palladium-catalyzed transformations, while the bromine handle enables efficient functionalization. This bench-stable compound serves as a key building block in synthetic organic chemistry and materials science applications.

Application

5-Bromo-1-phenyl-1H-benzo[d]imidazole serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its well-defined bromine handle. The molecule exhibits excellent bench stability and compatibility with standard reaction conditions, facilitating efficient functionalization at the 5-position. Its rigid aromatic core and defined substitution pattern support predictable reactivity in the construction of complex scaffolds relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  16588-25-3
- ~%
- In-stock
  
  221636-18-6
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 13, # 15 p. 2485 - 2488
Route2
- 74497-02-2
- ~%
- In-stock
  
  221636-18-6
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 13, # 15 p. 2485 - 2488
Route3
- In-stock
  
  68765-53-7
- 149-73-5
- ~%
- In-stock
  
  221636-18-6
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 13, # 15 p. 2485 - 2488

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

Quality Control

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Computational Chemistry Data

TPSA 17.82
LogP 3.788
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Benzimidazole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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5-Bromo-1-phenyl-1H-benzo[d]imidazole

CAS No. 221636-18-6

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