Production Method 1

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  22 h, 20 - 25 °C

Reference

Preparation of (2-(1H-imidazol-4-yl)phenyl)methanol

, China, , ,

Production Method 2

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  24 h, 20 °C

Reference

Discovery of imidazoleisoindole derivatives as potent IDO1 inhibitors: Design, synthesis, biological evaluation and computational studies

Zou, Yi ; Wang, Fang; Wang, Yan; Sun, Qirui; Hu, Yue; et al, European Journal of Medicinal Chemistry, 2017, 140, 293-304

Production Method 3

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  0 °C; 10 min, 0 °C
1.2 16 h, rt

Reference

Preparation of cyclohexyl-ethyl substituted diaza- and triaza-tricyclic compounds as indole-amine-2,3-dioxygenase (IDO) antagonists for the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 4

288-32-4

76-83-5

96797-15-8

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Potassium triiodide Solvents: Water
1.2 Reagents: Sodium sulfite Solvents: 1-Butanol ;  36 h, rt
1.3 Reagents: Triethylamine Solvents: Dimethylformamide

Reference

Azido and desamino analogs of the marine natural product oroidin

Anders, Lisa; Lindel, Thomas, Zeitschrift fuer Naturforschung, 2023, 78(3-4), 181-187

Production Method 5

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  0 °C; 14 h, rt
1.2 Solvents: Water ;  20 min, rt

Reference

Preparation of nitrogen-containing heteroaryl compounds as autotaxin inhibitors

, World Intellectual Property Organization, , ,

Production Method 6

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  1.5 h, reflux; cooled

Reference

4-Benzyl-1H-imidazoles with Oxazoline Termini as Histamine H3 Receptor Agonists

Wijtmans, Maikel; Celanire, Sylvain; Snip, Erwin; Gillard, Michel R.; Gelens, Edith; et al, Journal of Medicinal Chemistry, 2008, 51(10), 2944-2953

Production Method 7

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  rt; 24 h, rt

Reference

Imidazoisoindole compound as IDO1 inhibitor, and preparing method and application thereof

, China, , ,

Production Method 8

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  cooled; 17 h, 25 °C

Reference

Preparation of aralkyl-imidazoles as aldosterone synthase inhibitors

, Japan, , ,

Production Method 9

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  cooled; 17 h, 25 °C

Reference

Preparation of radioactive halogen-labeled 1-benzyl-1H-imidazole compounds as diagnostic imaging agents

, Japan, , ,

Production Method 10

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  cooled; 17 h, 25 °C

Reference

Preparation of substituted 1-benzyl-1H-imidazole derivatives as aldosterone synthase inhibitors

, Japan, , ,

Production Method 11

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  48 h, rt

Reference

Preparation of macrolide pyridyl substituted erythromycin ketolide analogs as antibiotics

, World Intellectual Property Organization, , ,

Production Method 12

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Solvents: Dimethylformamide ;  24 h, rt

Reference

Preparation of C12 modified erythromycin macrolides and ketolides having antibacterial activity

, World Intellectual Property Organization, , ,

Production Method 13

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylacetamide ;  rt → 0 °C; 0 °C; 0 °C → rt; 48 h, rt
1.2 Reagents: Water

Reference

Preparation of heteroarylmorpholinyltriazine derivatives for use as kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 14

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dimethylformamide ;  48 h, rt

Reference

Preparation of fused imidazole compounds as indoleamine 2,3-dioxygenase inhibitors

, World Intellectual Property Organization, , ,

Production Method 15

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Tetrahydrofuran ;  rt; 1 h, 70 °C

Reference

Preparation of imidazo-pyrrolo-pyridinyl derivatives as IDO and TDO inhibitors for the treatment of IDO - and TDO - mediated diseases

, United Kingdom, , ,

Production Method 16

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  3 h, 70 °C

Reference

6,7-heterocyclic fused 5H-pyrrolo[1,2-c]imidazole derivatives and their use as indoleamine 2,3-dioxygenase (IDO) and/or tryptophan 2,3-dioxygenase (TD02) modulators

, World Intellectual Property Organization, , ,

Production Method 17

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Diisopropylethylamine Solvents: Dimethylformamide ;  20 °C

Reference

Design and synthesis of indoleamine 2,3- Dioxygenase 1 inhibitors and evaluation of their use as anti-tumor agents

Wen, Hui ; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; et al, Molecules, 2019, 24(11),

Production Method 18

76-83-5

71759-89-2

96797-15-8

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  overnight, rt → 80 °C

Reference

Imidazole-containing fused tricyclic compounds as IDO1 inhibitors and their preparation, pharmaceutical compositions and use in the treatment of cancer

, China, , ,

4-iodo-1-(triphenylmethyl)-1H-imidazole Raw materials

• Imidazole
• (chlorodiphenylmethyl)benzene
• 5-iodo-1H-imidazole

4-iodo-1-(triphenylmethyl)-1H-imidazole Preparation Products

• 4-iodo-1-(triphenylmethyl)-1H-imidazole (96797-15-8)

• 1. Enabling high-throughput single-animal gene-expression studies with molecular and micro-scale technologies
  Jason Wan Lab Chip, 2020,20, 4528-4538
• 2. Fast synthesis of copper nanoclusters through the use of hydrogen peroxide additive and their application for the fluorescence detection of Hg2+ in water samples?
  Liao Xiaoqing,Li Ruiyi,Li Zaijun,Sun Xiulan,Wang Zhouping,Liu Junkang New J. Chem., 2015,39, 5240-5248
• 3. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 4. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 5. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119

4-Iodo-1-(triphenylmethyl)-1H-imidazole (CAS No. 96797-15-8): A Versatile Building Block in Organic Synthesis

4-Iodo-1-(triphenylmethyl)-1H-imidazole (CAS No. 96797-15-8) is a highly valuable imidazole derivative that has gained significant attention in modern organic chemistry and pharmaceutical research. This iodo-substituted trityl-protected imidazole compound serves as a crucial intermediate for the synthesis of various biologically active molecules, particularly in the development of heterocyclic compounds and pharmaceutical ingredients.

The molecular structure of 4-iodo-1-(triphenylmethyl)-1H-imidazole features an imidazole ring protected at the 1-position by a triphenylmethyl (trityl) group, with an iodine atom at the 4-position. This unique arrangement makes it an excellent substrate for cross-coupling reactions, particularly palladium-catalyzed coupling reactions such as Suzuki, Stille, and Sonogashira couplings. Researchers frequently utilize this compound as a versatile building block in medicinal chemistry due to its stability and reactivity profile.

In pharmaceutical applications, 4-iodo-1-tritylimidazole serves as a precursor for the synthesis of various imidazole-containing drugs. The imidazole moiety is a common structural feature in many biologically active compounds, including antifungal agents, antihistamines, and proton pump inhibitors. The iodo substituent at the 4-position provides an excellent handle for further functionalization through modern transition metal-catalyzed reactions, making this compound particularly valuable in drug discovery programs.

The triphenylmethyl protecting group in 4-iodo-1-(triphenylmethyl)-1H-imidazole offers several advantages in synthetic chemistry. It provides steric protection to the nitrogen atom while maintaining the aromatic character of the imidazole ring. This protection strategy is particularly useful in multi-step syntheses where selective deprotection might be required. The trityl group can be removed under mild acidic conditions, allowing for the generation of N-unsubstituted imidazole derivatives when needed.

Recent advances in imidazole chemistry have highlighted the importance of iodoimidazole derivatives like CAS 96797-15-8 in the development of novel materials. These compounds have found applications in the synthesis of organic electronic materials, including organic light-emitting diodes (OLEDs) and organic photovoltaics. The ability to participate in various cross-coupling reactions makes 4-iodo-1-tritylimidazole particularly valuable for creating conjugated systems with tailored electronic properties.

From a synthetic chemistry perspective, 4-iodo-1-(triphenylmethyl)-1H-imidazole offers excellent solubility in common organic solvents such as dichloromethane, tetrahydrofuran, and dimethylformamide. This property facilitates its use in various solution-phase reactions and makes it compatible with standard laboratory techniques. The compound typically appears as a white to off-white crystalline solid with good stability under standard storage conditions, though it should be protected from light due to the iodo substituent's photosensitivity.

The growing interest in imidazole-based compounds in medicinal chemistry has increased the demand for high-quality imidazole building blocks like 4-iodo-1-(triphenylmethyl)-1H-imidazole. Pharmaceutical researchers value this compound for its ability to serve as a precursor to various biologically active imidazoles through straightforward synthetic transformations. Its applications extend to the development of potential kinase inhibitors, GPCR modulators, and other targeted therapeutics that are currently hot topics in drug discovery.

In material science applications, the iodoimidazole derivative CAS 96797-15-8 has shown promise in the development of coordination polymers and metal-organic frameworks (MOFs). The imidazole nitrogen atoms can coordinate to metal centers, while the iodo substituent offers additional sites for structural modification. These properties make it a valuable component in designing functional materials with potential applications in gas storage, separation technologies, and catalysis.

Quality control of 4-iodo-1-(triphenylmethyl)-1H-imidazole typically involves analytical techniques such as high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry. These methods ensure the compound meets the purity standards required for pharmaceutical and advanced material applications. The iodo content is particularly important to verify, as it directly affects the compound's reactivity in subsequent synthetic steps.

As research into heterocyclic compounds continues to expand, 4-iodo-1-tritylimidazole maintains its position as a valuable tool for synthetic chemists. Its combination of protective group chemistry and reactive iodo functionality provides unique opportunities for molecular design. The compound's stability, coupled with its versatility in metal-catalyzed reactions, ensures its continued relevance in both academic and industrial research settings focused on imidazole chemistry and drug discovery.

The future applications of 4-iodo-1-(triphenylmethyl)-1H-imidazole (CAS No. 96797-15-8) appear promising, particularly in emerging areas such as click chemistry and bioconjugation. The compound's ability to participate in various cross-coupling reactions while maintaining the protected imidazole nitrogen makes it attractive for creating complex molecular architectures. As synthetic methodologies continue to advance, this iodo-substituted imidazole derivative will likely find new applications in both pharmaceutical development and materials science.

• 67478-46-0(2-Iodo-1-trityl-1H-imidazole)
• 536760-32-4(1-Benzyl-4-iodoimidazole)
• 959034-55-0(Imidazole, 4,5-diiodo-1-triphenylmethyl-)
• 67478-52-8(Lithium, [1-(triphenylmethyl)-1H-imidazol-2-yl]-)
• 881178-65-0(1H-IMIDAZOLE, 4,5-DIIODO-1-(1-PHENYLETHYL)-)
• 191544-97-5(5-iodo-1-(triphenylmethyl)-1H-imidazole)
• 15469-97-3(1-Tritylimidazole)
• 157255-72-6(4-Iodo-2-methyl-1-trityl-1H-imidazole)
• 105013-88-5(1H-Imidazole, 2-fluoro-4-iodo-1-(triphenylmethyl)-)
• 583-61-9(2,3-Dimethylpyridine)