2024-83-1

Basic information

• Product Name: 2,3-DIMETHOXYBENZONITRILE
• Synonyms: LABOTEST-BB LT00159775;BENZONITRILE, 2,3-DIMETHOXY-;AKOS BBS-00004470;AKOS B004317;3-CYANOVERATROLE;3,4-DIMETHOXYBENZONITRILE;4-CYANO-1,2-DIMETHOXYBENZENE;4-CYANOVERATROLE
• CAS NO: 2024-83-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 217-969-2
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Nitrile;Anisoles, Alkyloxy Compounds & Phenylacetates;Nitriles;Phenyls & Phenyl-Het;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C8 to C9;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Verapamil/Denopamine
• Mol File: 2024-83-1.mol
• Article Data: 170

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 290.25°C (rough estimate)
• Flash Point: >230 °F
• Appearance: white to light yellow crystal
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 0.00877mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in methanol.
• BRN: 1451651
• CAS DataBase Reference: 2,3-DIMETHOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXYBENZONITRILE(2024-83-1)
• EPA Substance Registry System: 2,3-DIMETHOXYBENZONITRILE(2024-83-1)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3276
• WGK Germany: 3
• RTECS: DI4355000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2024-83-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
2,3-DIMETHOXYBENZONITRILE is utilized as an intermediate in the synthesis of various organic compounds. Its specific structure allows it to be a versatile building block for the creation of a wide range of chemical products, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2,3-DIMETHOXYBENZONITRILE serves as a key intermediate for the development of new drugs. Its unique chemical properties enable the synthesis of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Agrochemical Industry:
2,3-DIMETHOXYBENZONITRILE is also employed in the agrochemical industry as a precursor for the synthesis of pesticides and other crop protection agents. Its incorporation into these products can lead to the development of more effective and environmentally friendly solutions for agricultural use.
Used in Specialty Chemicals:
Furthermore, 2,3-DIMETHOXYBENZONITRILE finds applications in the production of specialty chemicals, such as dyes, pigments, and fragrances. Its distinctive chemical structure contributes to the creation of innovative and high-quality products in these industries.

Preparation

Veratraldoxime(88–89 g, 0.45 mol) was combined with acetic anhydride (100 g) in a 300-mL round-bottomed flask equipped with a ground-glass air condenser, and the mixture was cautiously heated. A vigorous reaction took place, at which point the flame (heating by oil bath; the author) was removed. After the reaction had subsided, the solution was gently refluxed for 2 h and then carefully poured, with stirring, into cold water (300 mL). Stirring was continued, and on cooling the nitrile separated as small, almost colorless crystals; these were collected by filtration and dried in air. The veratronitrile thus obtained was quite pure; yield 57–62 g (72–76%); mp 66–67 C°. 1-Cyanoacenaphthene 1403 can be synthesized from its carbaldoxime by dehydration with acetic anhydride in 87% yield. Whereas acetic anhydride usually serves as the solvent as well as the reactant, this procedure is performed in n-octane.

Synthesis Reference(s)

Synthesis, p. 510, 1985 DOI: 10.1055/s-1985-31253

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

Upstream product

• 110-86-1 pyridine 
• 684-78-6 O,N-bis-(trifluoroacetyl)-hydroxylamine 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 71-43-2 benzene 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 76195-87-4 N-isoquinolinio-3,4-dimethoxy(thiobenzamidate) 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 77-78-1 dimethyl sulfate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 91-16-7 1,2-dimethoxybenzene 
• 506-68-3 bromocyane 
• 13181-13-0 β-veratraldehyde-[O-(2,4-dinitro-phenyl)-oxime ] 

Downstream Products

• 17345-61-8 3,4-dihydroxybenzonitrile 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 
• 102714-71-6 4,5-dimethoxy-2-nitrobenzonitrile 
• 52805-46-6 2-methoxy-5-cyanophenol 
• 1041381-45-6 2-(3,4-dimethoxyphenyl)-oxazolo[4,5:1,2][60]fullerene 

Relevant articles and documents

Effect of crown ether macrocycle on the methylation of the thioamide derivatives of benzo-15-crown-5 and veratrole

It was shown that benzo-15-crown-5 ether has an effect on the methylation of the thioamide derivatives. leading to the formation of the nitriles of carboxylic acids.

Inductively heated oxides inside microreactors - Facile oxidations under flow conditions

Inductively heated iron oxides mixed with solid oxidants like CrO 2 and NiO2 efficiently oxidize organic substrates under flow conditions in fixed-bed reactors.

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.

Dehydration of aldoximes to nitriles using trichloroacetonitrile without catalyst

Trichloroacetonitrile has been found to be an efficient dehydrating agent for a range of aldoximes including aromatic and heterocyclic aldoxime yielding the corresponding nitriles in moderate to good yields. The dehydration reactions can take place in non-acetonitrile media without the aid of a metal catalyst. In addition, it has been confirmed that trichloroacetonitrile was converted into trichloroacetamide in the reaction.

Highly Efficient Oxidative Cyanation of Aldehydes to Nitriles over Se,S,N-tri-Doped Hierarchically Porous Carbon Nanosheets

Oxidative cyanation of aldehydes provides a promising strategy for the cyanide-free synthesis of organic nitriles. Design of robust and cost-effective catalysts is the key for this route. Herein, we designed a series of Se,S,N-tri-doped carbon nanosheets with a hierarchical porous structure (denoted as Se,S,N-CNs-x, x represents the pyrolysis temperature). It was found that the obtained Se,S,N-CNs-1000 was very selective and efficient for oxidative cyanation of various aldehydes including those containing other oxidizable groups into the corresponding nitriles using ammonia as the nitrogen resource below 100 °C. Detailed investigations revealed that the excellent performance of Se,S,N-CNs-1000 originated mainly from the graphitic-N species with lower electron density and synergistic effect between the Se, S, N, and C in the catalyst. Besides, the hierarchically porous structure could also promote the reaction. Notably, the unique feature of this metal-free catalyst is that it tolerated other oxidizable groups, and showed no activity on further reaction of the products, thereby resulting in high selectivity. As far as we know, this is the first work for the synthesis of nitriles via oxidative cyanation of aldehydes over heterogeneous metal-free catalysts.

Copper-Catalyzed One-Pot Synthesis of Quinazolinones from 2-Nitrobenzaldehydes with Aldehydes: Application toward the Synthesis of Natural Products

A novel, efficient, and atom-economical approach for the construction of quinazolinones from 2-nitrobenzaldehydes has been unveiled via copper-catalyzed nitrile formation, hydrolysis, and reduction in one pot for the first time. In this reaction, urea is used as a source of nitrogen for nitrile formation, hydrazine hydrate is used for both the reduction of the nitro group and the hydrolysis of nitrile, and atmospheric oxygen is used as the sole oxidant. The method portrays a wide substrate scope with good functional group tolerances. Moreover, this method was applied for the synthesis of schizocommunin, tryptanthrin, phaitanthrin-A, phaitanthrin-B, and 8H-quinazolino[4,3-b]quinazolin-8-one.

Efficient nitriding reagent and application thereof

The invention discloses an efficient nitriding reagent and application thereof, wherein the nitriding reagent comprises nitrogen oxide, an active agent, a reducing agent and an organic solvent. By applying the nitriding reagent, nitrogen-containing compounds such as amide, nitrile and the like can be produced, and the method is simple in condition, low in waste discharge amount and simple in reaction equipment.

Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction

Two series of chalcone/aryl carboximidamide hybrids 4a–f and 6a–f were synthesised and evaluated for their inhibitory activity against iNOS and PGE2. The most potent derivatives were further checked for their in?vivo anti-inflammatory activity utilising carrageenan-induced rat paw oedema model. Compounds 4c, 4d, 6c and 6d were proved to be the most effective inhibitors of PGE2, LPS-induced NO production, iNOS activity. Moreover, 4c, 4d, 6c and 6d showed significant oedema inhibition ranging from 62.21% to 78.51%, compared to indomethacin (56.27 ± 2.14%) and celecoxib (12.32%). Additionally, 4c, 6a and 6e displayed good COX2 inhibitory activity while 4c, 6a and 6c exhibited the highest 5LOX inhibitory activity. Compounds 4c, 4d, 6c and 6d fit nicely into the pocket of iNOS protein (PDB ID: 1r35) via the important amino acid residues. Prediction of physicochemical parameters exhibited that 4c, 4d, 6c and 6d had acceptable physicochemical parameters and drug-likeness. The results indicated that chalcone/aryl carboximidamides 4c, 4d, 6c and 6d, in particular 4d and 6d, could be used as promising lead candidates as potent anti-inflammatory agents.

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.

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.