Cas no 850429-59-3 (4-Bromo-1,2-dimethyl-1H-imidazole)

4-Bromo-1,2-dimethyl-1H-imidazole is a brominated imidazole derivative characterized by its stable heterocyclic structure, featuring a bromine substituent at the 4-position and methyl groups at the 1- and 2-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. Its bromine moiety enhances reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, enabling efficient derivatization. The dimethyl substitution improves steric and electronic properties, contributing to controlled selectivity in synthetic pathways. High purity grades are available for research and industrial applications, ensuring reproducibility in complex syntheses. Proper handling under inert conditions is recommended due to its sensitivity to moisture and air.
4-Bromo-1,2-dimethyl-1H-imidazole structure
850429-59-3 structure
Product Name:4-Bromo-1,2-dimethyl-1H-imidazole
CAS No:850429-59-3
MF:C5H7BrN2
MW:175.026479959488
MDL:MFCD06659901
CID:727113
PubChem ID:7204875
Update Time:2025-10-28

4-Bromo-1,2-dimethyl-1H-imidazole Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-1,2-dimethyl-1H-imidazole
    • 1H-Imidazole,4-bromo-1,2-dimethyl-
    • 4-bromo-1,2-dimethylimidazole
    • 1H-Imidazole,4-bromo-1,2-dimethyl
    • 4-Bromo-1,2-dimethyl-1H-imidazole (ACI)
    • MFCD06659901
    • DTXSID10428397
    • AKOS002657980
    • FZRKTLGQQTWOMJ-UHFFFAOYSA-N
    • CS-0038736
    • 1H-Imidazole, 4-bromo-1,2-dimethyl-
    • SY025017
    • EN300-101075
    • 4-Bromo-1,2-dimethyl-1H-imidazole, AldrichCPR
    • SCHEMBL104447
    • 850429-59-3
    • AB26584
    • Q-103114
    • AS-39505
    • 4-bromo-1,2-dimethyl-imidazole
    • MDL: MFCD06659901
    • Inchi: 1S/C5H7BrN2/c1-4-7-5(6)3-8(4)2/h3H,1-2H3
    • InChI Key: FZRKTLGQQTWOMJ-UHFFFAOYSA-N
    • SMILES: BrC1=CN(C)C(C)=N1

Computed Properties

  • Exact Mass: 173.97900
  • Monoisotopic Mass: 173.979
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 86.5
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.6
  • Topological Polar Surface Area: 17.8A^2

Experimental Properties

  • Density: 1.58±0.1 g/cm3 (20 oC 760 Torr)
  • Melting Point: 40-44
  • Boiling Point: 266.6 ℃ at 760 mmHg
  • Flash Point: 115.0±19.8℃
  • Refractive Index: 1.589
  • PSA: 17.82000
  • LogP: 1.49100

4-Bromo-1,2-dimethyl-1H-imidazole Security Information

  • Hazard Statement: Irritant
  • Hazard Category Code: 22
  • Hazardous Material Identification: Xi

4-Bromo-1,2-dimethyl-1H-imidazole Customs Data

  • HS CODE:2933290090
  • Customs Data:

    China Customs Code:

    2933290090

    Overview:

    2933290090. Other compounds with non fused imidazole ring in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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4-Bromo-1,2-dimethyl-1H-imidazole Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  1 h, -25 °C; 1 h, -25 °C
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
Cost-Effective and Scalable Synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole: A Key Building Block for Bioactive Molecules
Vetrichelvan, Muthalagu ; et al, SynOpen, 2023, 7(4), 496-500

Production Method 2

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  6 h, rt
2.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ;  1 h, -25 °C; 1 h, -25 °C
2.2 Reagents: Ammonium chloride Solvents: Water
Reference
Cost-Effective and Scalable Synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole: A Key Building Block for Bioactive Molecules
Vetrichelvan, Muthalagu ; et al, SynOpen, 2023, 7(4), 496-500

Production Method 3

Reaction Conditions
1.1 Reagents: Tetramethylammonium fluoride Solvents: Dimethyl sulfoxide ;  100 °C
Reference
Cost-Effective and Scalable Synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole: A Key Building Block for Bioactive Molecules
Vetrichelvan, Muthalagu ; et al, SynOpen, 2023, 7(4), 496-500

Production Method 4

Reaction Conditions
1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  6 h, rt
2.1 Reagents: Tetramethylammonium fluoride Solvents: Dimethyl sulfoxide ;  100 °C
Reference
Cost-Effective and Scalable Synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole: A Key Building Block for Bioactive Molecules
Vetrichelvan, Muthalagu ; et al, SynOpen, 2023, 7(4), 496-500

4-Bromo-1,2-dimethyl-1H-imidazole Raw materials

4-Bromo-1,2-dimethyl-1H-imidazole Preparation Products

4-Bromo-1,2-dimethyl-1H-imidazole Suppliers

Amadis Chemical Company Limited
Gold Member
Audited Supplier Audited Supplier
(CAS:850429-59-3)4-Bromo-1,2-dimethyl-1H-imidazole
Order Number:A854924
Stock Status:in Stock
Quantity:25g/5g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 07:53
Price ($):1003.0/201.0

Additional information on 4-Bromo-1,2-dimethyl-1H-imidazole

Professional Introduction to 4-Bromo-1,2-dimethyl-1H-imidazole (CAS No. 850429-59-3)

4-Bromo-1,2-dimethyl-1H-imidazole is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical and chemical research due to its versatile structural properties and potential applications. This compound, identified by the CAS number 850429-59-3, belongs to the imidazole class of molecules, which are well-known for their presence in numerous biologically active compounds. The presence of both bromine and methyl substituents in its structure enhances its reactivity, making it a valuable intermediate in synthetic chemistry.

The imidazole ring is a five-membered aromatic heterocycle containing two nitrogen atoms at positions 1 and 3. This structural motif is crucial for the compound's interaction with biological targets, as it mimics the binding sites of various natural products and pharmaceuticals. The addition of bromine at the 4-position and methyl groups at the 1 and 2 positions introduces specific electronic and steric effects that can be exploited in drug design and material science applications.

In recent years, 4-Bromo-1,2-dimethyl-1H-imidazole has been extensively studied for its role in the synthesis of novel pharmaceuticals. Its brominated structure makes it an excellent precursor for further functionalization via cross-coupling reactions, such as Suzuki-Miyaura, Heck, and Buchwald-Hartwig couplings. These reactions are fundamental in constructing complex molecular architectures that are often found in modern drugs. For instance, researchers have utilized this compound to develop inhibitors targeting various enzymes involved in cancer pathways.

One of the most compelling aspects of 4-Bromo-1,2-dimethyl-1H-imidazole is its application in medicinal chemistry. The bromine atom serves as a versatile handle for introducing additional functional groups through palladium-catalyzed reactions, enabling the creation of diverse pharmacophores. Recent studies have demonstrated its utility in designing small-molecule modulators of protein-protein interactions, which are critical for developing treatments against complex diseases like Alzheimer's and Parkinson's.

The compound's methyl groups at positions 1 and 2 contribute to its overall steric environment, influencing how it interacts with biological targets. This fine-tuning of steric properties can lead to improved selectivity and efficacy in drug candidates. For example, modifications based on this scaffold have shown promise in inhibiting kinases, which are overactive in many forms of cancer. The ability to modify these positions allows chemists to explore a wide range of structural variations, optimizing potency and minimizing side effects.

Moreover, 4-Bromo-1,2-dimethyl-1H-imidazole has found applications beyond pharmaceuticals. In materials science, its unique electronic properties make it a candidate for organic semiconductors and light-emitting diodes (OLEDs). The bromine substituent can be used to tailor the compound's solubility and thermal stability, which are essential factors in device performance. Researchers have reported its incorporation into π-conjugated systems, enhancing charge transport properties necessary for advanced electronic applications.

The synthesis of 4-Bromo-1,2-dimethyl-1H-imidazole typically involves multi-step processes starting from commercially available precursors. One common route involves the bromination of a dimethylimidazole derivative followed by methylation at the appropriate positions. Advances in synthetic methodologies have improved yields and purity, making it more accessible for large-scale applications. Catalytic processes have also been optimized to minimize waste and energy consumption, aligning with green chemistry principles.

In conclusion, 4-Bromo-1,2-dimethyl-1H-imidazole (CAS No. 850429-59-3) is a multifaceted compound with significant potential in both pharmaceuticals and materials science. Its unique structural features enable diverse functionalization strategies, making it a valuable building block for drug discovery and advanced materials development. As research continues to uncover new applications for this compound, its importance is likely to grow further, driving innovation across multiple scientific disciplines.

Recommended suppliers
Amadis Chemical Company Limited
(CAS:850429-59-3)4-Bromo-1,2-dimethyl-1H-imidazole
A854924
Purity:99%/99%
Quantity:25g/5g
Price ($):1003.0/201.0
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