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• 2. An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand?
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• 3. An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders
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• 4. An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines?
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Dimethoxybenzenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Methoxybenzenes Dimethoxybenzenes

Research Brief on 3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile (CAS: 35249-62-8): Recent Advances and Applications

3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile (CAS: 35249-62-8) is a brominated aromatic compound with significant potential in medicinal chemistry and drug discovery. Recent studies have highlighted its utility as a key intermediate in the synthesis of bioactive molecules, particularly those targeting neurological disorders and cancer. This research brief synthesizes the latest findings regarding this compound's chemical properties, synthetic applications, and biological activities, with a focus on peer-reviewed publications from 2022-2024.

Structural analysis reveals that the electron-withdrawing nitrile group and bromine substituent at the 2-position make this compound particularly reactive in palladium-catalyzed cross-coupling reactions. A 2023 study in Journal of Medicinal Chemistry demonstrated its effectiveness in Buchwald-Hartwig aminations for creating novel dopamine receptor modulators, achieving yields >85% when using XPhos as the ligand. The dimethoxy groups appear to enhance compound stability while maintaining sufficient reactivity for further derivatization.

In cancer research, derivatives of 35249-62-8 have shown promising activity against protein kinase C (PKC) isoforms. A recent ACS Chemical Biology publication reported that structural analogs inhibit PKCδ with IC50 values in the low micromolar range (2.3-5.8 μM), suggesting potential as lead compounds for hematologic malignancies. Molecular docking studies indicate the bromine atom plays a critical role in binding to the C1B domain of PKCδ through halogen bonding interactions.

Notably, the compound has emerged as a crucial building block in the synthesis of σ receptor ligands. Research from the University of Tokyo (2024) utilized 3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile as the starting material for developing σ1 receptor agonists with neuroprotective effects in Parkinson's disease models. The lead compound showed 87% reduction in dopaminergic neuron loss at 10 mg/kg dosage in murine studies.

From a synthetic chemistry perspective, recent advances have improved the production efficiency of 35249-62-8. A 2023 Organic Process Research & Development paper detailed an optimized three-step synthesis from vanillin with an overall yield of 68%, representing a 22% improvement over previous methods. Key innovations included microwave-assisted bromination and continuous flow hydrogenation techniques that reduced reaction times from 48 hours to under 8 hours.

Safety and handling considerations have also been updated in recent literature. While the compound shows moderate acute toxicity (LD50 = 320 mg/kg in rats), proper personal protective equipment including nitrile gloves and chemical goggles is recommended when handling. Storage under nitrogen at -20°C has been shown to maintain stability for >24 months according to stability studies published in 2024.

Future research directions appear focused on expanding the structural diversity of 35249-62-8 derivatives through late-stage functionalization strategies. Particularly promising are photoredox-catalyzed C-H activation approaches that could enable direct modification of the dimethoxy aromatic ring. Several pharmaceutical companies have included this compound in their fragment-based drug discovery libraries, suggesting continued interest in its medicinal chemistry potential.

• 51655-39-1(2-Bromo-4,5-dimethoxyphenylacetonitrile)
• 106053-67-2(Benzene, 1-bromo-4,5-dimethoxy-2-(2-phenylethyl)-)
• 348618-45-1(Benzenepropanenitrile, 2-bromo-5-methoxy-4-(phenylmethoxy)-)
• 847744-26-7(2-(2-Bromo-4,5-diethoxyphenyl)acetonitrile)
• 27452-03-5(3-(6-bromo-1,3-dioxaindan-5-yl)propanenitrile)
• 83996-74-1(BENZENEPROPANENITRILE, 6-BROMO-2,3-DIMETHOXY-)
• 81038-45-1(2-(2-bromo-5-hydroxy-4-methoxyphenyl)acetonitrile)
• 84003-65-6(BENZENEPROPANENITRILE, 2-BROMO-4,5-DIHYDROXY-)
• 65853-40-9(BENZENEPROPANENITRILE, 2-BROMO-5-ETHOXY-)
• 557056-03-8(BENZENEHEPTANENITRILE, 2-BROMO-4-METHOXY-)