Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

Name: Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate
Brand: ChemScene
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CAS No. 705280-65-5
Cat. No. CS-0158814
Molecule weight263.05
Purity≥97%
MDL No.MFCD09702026

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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+
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Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate|CS-0158814

Structure of 705280-65-5

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General Information

CAS No. 705280-65-5
Cat. No. CS-0158814
Purity ≥97%
MDL No. MFCD09702026
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₇BrN₂O₄
Molecular Weight 263.05
Synonym(s) 1H-Imidazole-4,5-dicarboxylic acid, 2-bromo-, dimethyl ester
SMILES O=C(C1=C(C(OC)=O)NC(Br)=N1)OC

Description

Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring a bromine substituent at the 2-position and two ester groups at the 4 and 5 positions. This configuration enables direct functionalization in cross-coupling reactions and facilitates incorporation into complex molecular architectures.

Application

Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to substituted imidazoles via palladium-catalyzed cross-coupling reactions. The bromo group facilitates C–C bond formation under mild conditions, while the two ester functionalities allow for selective derivatization or hydrolysis. Its bench-stable nature and compatibility with diverse functional groups make it ideal for constructing complex scaffolds in medicinal chemistry and agrochemical research.

Synthesis

Route1
- In-stock
  
  3304-70-9
- ~96%
- In-stock
  
  705280-65-5
References
- Eckhardt, Matthias; Hauel, Norbert; Langkopf, Elke; Himmelsbach, Frank Tetrahedron Letters, 2008 , vol. 49, # 12 p. 1931 - 1934
Route2
- 945229-35-6
- ~%
- In-stock
  
  705280-65-5
References
- Bioorganic and Medicinal Chemistry, , vol. 15, # 14 p. 4933 - 4945

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

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Computational Chemistry Data

TPSA 81.28
LogP 0.7454
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Imidazole compounds

Key Words

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Dimethyl 2-bromo-1H-imidazole-4,5-dicarboxylate

CAS No. 705280-65-5

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