17345-61-8

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydroxybenzonitrile is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific diseases or conditions.
Used in Chemical Synthesis:
3,4-Dihydroxybenzonitrile serves as a valuable building block in the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals. Its reactivity and functional groups make it a versatile starting material for various chemical reactions.
Used in Material Science:
In the field of material science, 3,4-dihydroxybenzonitrile can be used to develop novel materials with specific properties, such as improved conductivity, enhanced stability, or unique optical characteristics. Its incorporation into polymers or other materials can lead to the creation of advanced materials with potential applications in various industries.
Used in Research and Development:
3,4-Dihydroxybenzonitrile is also utilized in research and development settings, where it can be employed to study the properties of new compounds, test the effectiveness of various reaction conditions, or explore the potential applications of newly synthesized materials. Its unique chemical structure makes it an interesting subject for scientific investigation and experimentation.

InChI:InChI=1/C7H5NO2/c8-4-5-1-2-6(9)7(10)3-5/h1-3,9-10H

Upstream product

• 861531-72-8 2-oxo-benzo[1,3]dioxole-5-carbonitrile 
• 3343-59-7 3,4-dihydroxybenzaldehyde oxime 
• 107-03-9 1-thiopropane 
• 4421-09-4 piperonylonitrile 
• 767-00-0 4-cyanophenol 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 7732-18-5 water 
• 3897-89-0 4-(hydroxymethyl)benzene-1,2-diol 
• 37491-68-2 3,4-dihydroxybenzylamine 
• 120-57-0 piperonal 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 
• 1344113-49-0 C₁₅H₂₃NO₂Si 
• 34916-10-4 4-cyanocyclohexanone 

Downstream Products

• 519-34-6 maclurin 
• 103278-74-6 3,4-bis-[5-(4-cyano-phenoxy)-pentyloxy]-benzonitrile 
• 83306-82-5 3,4-Dihydroxybenzimidsaeureethylesterhydrochlorid 
• 185038-16-8 Trifluoro-methanesulfonic acid 5-cyano-2-trifluoromethanesulfonyloxy-phenyl ester 
• 244020-33-5 3,4-bis[3,7-(S)-dimethyl-6-octenyloxy]benzonitrile 
• 54337-90-5 3,4-dihydroxy benzamid 
• 601491-68-3 methanesulfonic acid 2-(2-{5-cyano-2-[2-(2-methanesulfonyloxy-ethoxy)-ethoxy]-phenoxy}-ethoxy)-ethyl ester 
• 111296-38-9 3-hydroxy-4,4'-pentanediyldioxy-bis-benzamidine; dihydrochloride 
• 194985-94-9 3-hydroxy-4-(benzyloxy)benzonitrile 
• 198474-57-6 3,4-didecyloxybenzamidine 
• 47836-89-5 ferroin 

Relevant academic research and scientific papers

Mechanism of bromoxynil phototransformation: Effect of medium and surfactant

Bromoxynil (BXN, 3,5-dibromo-4-hydroxybenzonitrile) is a herbicide that is classified as a highly hazardous chemical, toxic for the reproduction. The processes and mechanisms regarding the fate of this compound in the environmental compartments subject to

Sodium bis(trimethylsilyl)amide in the 'one-flask' transformation of aromatic esters to nitriles

A new 'one-flask' method was developed for the conversion of aromatic esters to the corresponding nitriles by use of sodium bis(trimethylsilyl)amide.

Nitroxygenation of quercetin by HNO

The flavonol quercetin undergoes both enzymatic and non-enzymatic reactions with nitroxyl (HNO/NO-), similar to analogous reactions with dioxygen, but in which N is regioselectively found in the ring-cleaved product. Here we report on kinetic and thermodynamic analysis of the non-enzymatic nitroxygenation reaction in water, which is orders of magnitude faster than the comparable dioxygenation. The second order rate constants were determined from variable temperature reactions, which allowed determination of the reaction activation enthalpy (ΔH≠ = 9.4 kcal/mol), entropy (ΔS≠ = -8.3 cal/mol K), and free energy (ΔG≠ = 11.8 kcal/mol). The determined standard state energy (ΔGo) and activation free energy, as well as the low entropic energy of reaction, are consistent with a proposed single electron transfer (SET) rate determining step.

Significant enhancement of monooxygenase activity of oxygen carrier protein hemocyanin by urea

Oxygenation of a series of p-substituted phenols to the corresponding catechols (phenolase activity) by the (μ-η2:η2-peroxo)dicopper(II) species of Octopus hemocyanin has been directly examined for the first time by using a UV-vis spectroscopic method in a 0.5 M borate buffer solution containing 8 M urea under anaerobic conditions. Preliminary kinetic studies have indicated that the reaction involves an electrophilic aromatic substitution mechanism as in the case of phenolase reaction of tyrosinase. The oxygenation of phenols by hemocyanin also proceeded catalytically when the reaction was carried out under aerobic conditions. Copyright

Method for preparing 3, 4-dihydroxybenzonitrile

The invention discloses a method for preparing 3, 4-dihydroxybenzonitrile, which comprises the following step of: contacting vanillin with hydroxylamine hydrochloride and halide so as to obtain the 3, 4-dihydroxybenzonitrile. The method has the advantages of simplicity in operation, few byproducts, high product yield and the like, thereby being beneficial to industrial production.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Selective ether bond breaking method of aryl alkyl ether

The invention discloses a selective aryl alkyl ether cracking method, which comprises that aryl alkyl ether, aluminum iodide and an additive are subjected to a selective ether bond cleavage reaction in an organic solvent at a temperature of -20 DEG C to a reflux temperature to generate phenol and derivatives thereof. The method is mild in condition and simple and convenient to operate, is suitablefor cracking aryl alkyl ether containing o-hydroxyl and o-carbonyl and acetal ether, and can also be used for removing tertiary carbon hydroxyl protecting groups with higher steric hindrance, such astriphenylmethyl, tertiary butyl and the like.

Dearomatization of Electron-Deficient Phenols to ortho-Quinones: Bidentate Nitrogen-Ligated Iodine(V) Reagents

Despite their broad utility, the synthesis of ortho-quinones remains a significant challenge, in particular, access to electron-deficient derivatives remains an unsolved problem. Reported here is the first general method for the synthesis of electron-deficient ortho-quinones by direct oxidation of phenols. The reaction is enabled by a novel bidentate nitrogen-ligated iodine(V) reagent, a previously unexplored class of compounds which we have termed Bi(N)-HVIs. The reaction is extremely general and proceeds with excellent regioselectivity for the ortho over para isomer. Functionalization of the ortho-quinone products was examined, resulting in a facile one-pot synthesis of catechols, as well as the incorporation of a variety of heteroatom nucleophiles. This method represents the first synthetic application of Bi(N)-HVIs and demonstrates their potential as a platform for the further development of highly reactive, but also highly tunable, I(V) reagents.

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide-Dimethyl Sulfoxide

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o -hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

Direct Synthesis of Nitriles from Carboxylic Acids Using Indium-Catalyzed Transnitrilation: Mechanistic and Kinetic Study

Aliphatic and aromatic carboxylic acids can be quantitatively converted to the corresponding nitriles in the presence of catalysts using acetonitrile both as a solvent and reactant at 200 °C. This transformation is based on the acid-nitrile exchange (i.e., transnitrilation) and uses a nontoxic and water resistant catalyst, indium trichloride (InCl3). The mechanism of the transnitrilation was investigated both experimentally and computationally and compared to the previously proposed mechanism. In contrast to the usually assumed formation of amide as an intermediate, transnitrilation is an equilibrium reaction and proceeds via an equilibrated Mumm reaction with the formation of an imide as an intermediate. A simple and reversible mechanism was proposed for this reaction, which was validated by kinetics measurement and by density functional theory calculations of the reaction intermediates and reaction mechanisms.