4107-65-7

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxybenzonitrile is used as an intermediate in the synthesis of various pharmaceutical compounds. Its chemical structure allows for further functionalization and modification, making it a versatile building block for the development of new drugs.
Used in Chemical Synthesis:
2,4-Dimethoxybenzonitrile is used as a starting material for the preparation of other organic compounds, such as 2,4-dimethoxybenzylamine, which can be further utilized in the synthesis of various chemical products. Its unique functional groups enable it to serve as a key component in the creation of a wide range of molecules with different applications.
Used in Research and Development:
Due to its unique chemical properties, 2,4-Dimethoxybenzonitrile is also used in research and development for the exploration of new chemical reactions and the synthesis of novel compounds. It can be employed in academic and industrial laboratories to study the reactivity of its functional groups and to develop new synthetic routes for the production of various chemical products.

InChI:InChI=1/C9H9NO2/c1-11-8-4-3-7(6-10)9(5-8)12-2/h3-5H,1-2H3

Upstream product

• 39835-11-5 2-hydroxy-4 methoxybenzonitrile 
• 77-78-1 dimethyl sulfate 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 67-56-1 methanol 
• 1984-21-0 1-isocyano-2,4-dimethoxybenzene 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 151-50-8 potassium cyanide 
• 31874-34-7 2,4-dimethoxybenzaldoxime 
• 1521-95-5 2,4-dimethoxybenzamide 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 506-68-3 bromocyane 
• 151-10-0 1,3-Dimethoxybenzene 
• 64-17-5 ethanol 

Downstream Products

• 156630-35-2 4-(2,4-dimethoxybenzoyl)-2H-spiro 
• 154325-05-0 4-(2,4-dimethoxybenzoyl)-2,2-dimethyl-2H-thiochromene 
• 2735-04-8 2,4-Dimethoxyaniline 
• 3555-84-8 2,4-dimethoxybenzophenone 
• 23822-07-3 2,4-dimethoxy-thiobenzamide 
• 84224-29-3 4-hydroxy-2-methoxybenzonitrile 
• 64419-24-5 2,4-dihydroxybenzonitrile 
• 500024-82-8 N-hydroxy-2,4-dimethoxy-benzamidine 
• 39835-11-5 2-hydroxy-4 methoxybenzonitrile 
• 2571-54-2 2,4,6-trimethoxybenzonitrile 
• 548471-96-1 ethyl 2,4-dimethoxy-benzimidate hydrochloride 
• 20781-39-9 N-(p-Methoxy-benzyloxycarbonyl)-glycin- 
• 20781-37-7 N-Benzyloxycarbonyl-glycin- 
• 20839-74-1 p-Methoxy-benzyloxycarbonyl-glycyl-glycin-(2,4-dimethoxy-benzylamid) 

Relevant academic research and scientific papers

Envirocat EPZG(R), a new catalyst for the conversion of aldoximes into nitriles

The conversion of aldoximes into nitriles was carried out at 100°C in the absence of a solvent using Envirocat EPZG(R) as a new solid supported catalyst.

Electrochemical Oxidative C?H Cyanation of Quinoxalin-2(1H)-ones with TMSCN

Both quinoxalin-2(1H)-ones and nitriles are valuable organic compounds, and it is an interesting task to introduce cyano into quinoxalin-2(1H)-ones. Herein a regioselective C?H cyanation of quinoxalin-2(1H)-ones was developed with a nucleophilic cyano source TMSCN under electrochemical oxidative conditions. This process allowed the synthesis of C3 cyanated quinoxalin-2(1H)-ones in moderate to excellent yields in the absence of transition-metal catalysts and organic hydroperoxides.

SO2F2-mediated oxidation of primary and tertiary amines with 30% aqueous H2O2 solution

A highly efficient and selective oxidation of primary and tertiary amines employing SO2F2/H2O2/base system was described. Anilines were converted to the corresponding azoxybenzenes, while primary benzylamines were transformed into nitriles and secondary benzylamines were rearranged to amides. For tertiary amine substrates quinolines, isoquinolines and pyridines, their oxidation products were the corresponding N-oxides. The reaction conditions are very mild and just involve SO2F2, amines, 30% aqueous H2O2 solution, and inorganic base at room temperature. One unique advantage is that this oxidation system is just composed of inexpensive inorganic compounds without the use of any metal and organic compounds.

Method for converting aromatic aldehyde into aromatic nitrile by using sulfur powder promoted inorganic ammonium as nitrogen source (by machine translation)

The invention discloses a method for converting aromatic aldehyde into aromatic nitrile. The method is conversion of high yield of aromatic aldehyde one-pot reaction of sulfur powder promoted inorganic ammonium as a nitrogen source into aromatic nitrile. The method has the advantages of no need of metal participation, no need of strong oxide, compatibility of reaction to air, easiness in amplification to a gram scale and the like, and overcomes the problems of harsh reaction conditions, complex operation, low functional group compatibility and the like in the prior art. (by machine translation)

Zn-catalyzed cyanation of aryl iodides

We report the first example of zinc-catalyzed cyanation of aryl iodides with formamide as the cyanogen source. The transformation was promoted by the bisphosphine Nixantphos ligand. Under optimized conditions, a variety of electron-donating and electron-withdrawing aryl iodides were converted into nitrile products in good to excellent yields. This approach is an exceedingly simple and benign method for the synthesis of aryl nitriles and is likely to proceed via a dinuclear Zn-concerted catalysis.

Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction

The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Acceptorless dehydrogenation of amines to nitriles catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated bimetallic ruthenium (II) complex

We have developed a clean, atom-economical and environmentally friendly route for acceptorless dehydrogenation of amines to nitriles by combining a new dual N-heterocyclic carbene-nitrogen-phosphine ligand R(CNP)2 (R = o-xylyl) with a ruthenium precursor [RuCl2(η6-C6H6)]2. In this system, the electronic and steric factors of amines had a negligible influence on the reaction and a broad range of functional groups were well tolerated. All of the investigated amines could be converted to nitriles in good yield of up to 99% with excellent selectivity. The unprecedented catalytic performance of this system is attributed to the synergistic effect of two ruthenium centers chelated by R(CNP)2 and a plausible reaction mechanism is proposed according to the active species found via in situ NMR and HRMS.

Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical

This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.

Method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by Ru coordination compound

The invention discloses a method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by a Ru coordination compound. The method comprises: adding a Ru coordination compound, an alkali, a primary amine and an organic solvent into a reaction test tube according to a mol ratio of 1:100:(100-500):1000-3000, and carrying out a stirring reaction under the condition of 80 to120 DEG C; and when gas chromatography monitors that the raw materials completely disappear, stopping the reaction, collecting the reaction solution, centrifuging the reaction solution, taking the supernatant, extracting with dichloromethane, merging the organic phases, drying, filtering, evaporating the organic solvent under reduced pressure to obtain a filtrate, and carrying out column chromatography purification on the filtrate to obtain the target product nitrile. According to the invention, the catalyst is good in activity, single in catalytic system, good in product selectivity, simple in subsequent treatment and good in system universality after the reaction is finished, has a good catalytic effect on various aryl, alkyl and heteroaryl substituted primary amines, and also has a gooddehydrogenation performance on secondary amines.