52805-45-5

Usage

Uses

Used in Organic Chemistry Research:
3-Bromo-4-hydroxy-5-methoxybenzonitrile is used as a research compound for its versatile reactivity due to the presence of multiple functional groups. It is particularly valuable in the synthesis of complex organic molecules, where its ability to participate in various chemical reactions is crucial.
Used in Pharmaceutical Development:
3-Bromo-4-hydroxy-5-methoxybenzonitrile is used as a key intermediate in the development of pharmaceutical compounds. Its unique structure allows for the creation of new drug candidates, potentially leading to the discovery of novel therapeutic agents.
Used in Chemical Synthesis:
3-Bromo-4-hydroxy-5-methoxybenzonitrile is used as a synthetic building block in the preparation of a wide range of chemical products. Its functional groups enable it to be a versatile component in the creation of new materials and compounds with specific properties.
Used in Material Science:
3-Bromo-4-hydroxy-5-methoxybenzonitrile is used as a component in the development of new materials with tailored properties. Its inclusion in the synthesis process can lead to materials with improved characteristics, such as enhanced stability or specific reactivity, which can be applied in various industries.

InChI:InChI=1/C8H6BrNO2/c1-12-7-3-5(4-10)2-6(9)8(7)11/h2-3,11H,1H3

Upstream product

• 515847-71-9 4-acetoxy-3-bromo-5-methoxy-benzonitrile 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 6948-30-7 5-bromoveratralaldehyde 
• 121-33-5 vanillin 
• 1428637-17-5 C₉H₁₀BrNO₃ 
• 2556-04-9 4-(benzyloxy)-3-bromo-5-methoxybenzaldehyde 
• 52805-35-3 4-Benzyloxy-3-brom-5-methoxybenzonitril 

Downstream Products

• 115540-87-9 5-bromo-4-hydroxy-3-methoxythiobenzamide 

Relevant academic research and scientific papers

One pot synthesis of aryl nitriles from aromatic aldehydes in a water environment

In this study, we found a green method to obtain aryl nitriles from aromatic aldehyde in water. This simple process was modified from a conventional method. Compared with those approaches, we used water as the solvent instead of harmful chemical reagents. In this one-pot conversion, we got twenty-five aryl nitriles conveniently with pollution to the environment being minimized. Furthermore, we confirmed the reaction mechanism by capturing the intermediates, aldoximes.

CARBOXY SUBSTITUTED (HETERO) AROMATIC RING DERIVATIVES AND PREPARATION METHOD AND USES THEREOF

Carboxy-substituted (hetero)aryl derivatives, pharmaceutical compositions comprising these compounds, and methods of preparing such compounds and compositions are provided. The compounds or compositions are useful in inhibiting xanthine oxidase and urate anion transporter 1, and also can be used in the treatment or prevention of diseases associated with high blood uric acid level in mammals, especially humans.

Discovery of novel VEGFR-2 inhibitors. Part II: Biphenyl urea incorporated with salicylaldoxime

A series of novel VEGFR-2 inhibitors containing oxime as hinge binding fragment were described. A strategy of pseudo six-membered ring formed through intramolecular hydrogen bond was employed to mimic the planar quinazoline. The oxime group was firstly introduced to interact with hinge region of VEGFR-2. Most of compounds tested showed moderate to high VEGFR-2 inhibitory activity. In particular, 12l, 12p and 12y exhibited significant enzymatic inhibitory activity as well as potent antiproliferative activity against cancer cells. Molecular docking suggested that the salicylaldoxime formed two hydrogen bonds with hinge region. These biphenylureas could serve as promising lead compounds for developing novel anticancer agents.

Biphenyl derivatives incorporating urea unit as novel VEGFR-2 inhibitors: Design, synthesis and biological evaluation

A series of novel biphenyl urea derivates were synthesized and investigated for their potential to inhibit vascular endothelial growth factor receptor-2 (VEGFR-2). In particular, A7, B3 and B4 displayed significant enzymatic inhibitory activities, with IC50 values of 4.06, 4.55 and 5.26 nM. Compound A7 exhibited potent antiproliferative activity on several cell lines. SAR study suggested that the introduction of methyl at ortho-position of the biphenyl urea and tertiary amine moiety could improve VEGFR-2 inhibitory activity and antitumor effects. Molecular docking indicated that the urea moiety formed four hydrogen bonds with DFG residue. These biphenyl ureas could serve as promising lead compounds for further optimization.

Design, synthesis and biological evaluation of biphenyl urea derivatives as novel VEGFR-2 inhibitors

VEGFR-2 plays a critical role in vasculogenesis and VEGFR-2 inhibitors have been widely used in the treatment of cancer. In our continued efforts to search for potent and novel VEGFR-2 inhibitors as antitumor agents, we have identified a potent lead compound (HMQ-16) bearing a biphenyl scaffold. Rearrangement and replacement of arylcarbamoyl in HMQ-16 with a urea moiety generated a series of novel VEGFR-2 inhibitors. In order to enhance the affinity with VEGFR-2, the 4′-acetyl group was converted to an oxime group. Fourteen biphenyl urea derivatives were designed and synthesized as potent VEGFR-2 inhibitors. Six of them (T2, T5, T7, T9, T11, T14) exhibited potent VEGFR-2 inhibitory activity comparable to that of sorafenib. Compound T7 was the most potent with an IC 50 value of 1.08 nM. The enzymatic and cellular assays suggested that T7 has potential as a valuable lead compound for further optimization.

Ruthenium-catalyzed intramolecular selective halogenation of O-methylbenzohydroximoyl halides: A new route to halogenated aromatic nitriles

The intramolecular halogenation of O-methylbenzohydroximoyl halides in the presence of a Ru catalyst and the ligand diphenylacetylene afforded halo substituted aromatic nitriles in a highly regioselective manner. Further, substituted nitriles were converted into substituted tetrazole derivatives in the presence of NaN3 and I2.

Synthesis and Antitubercular Activity of 4-(5-Nitro-2-furyl/2-pyrazinyl/1-adamantyl)-2-(alkyl/aryl/arylamino)thiazoles

The reaction of haloketones, obtained from Arndt-Eistert reaction on the acid chlorides of 1-adamantane, 5-nitrofuroic acid and pyrazine-2-carboxylic acid, with different thioamides and thioureas affords the title thiazoles (I-III).Some of them exhibit interesting antitubercular activity at 6.25 to 0.38 μg/ml concentration against H37Rv strain of M. tubercolosis in vitro testing.The structure activity relationship (SAR) has also been discussed.