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

Chemical Properties

white to light yellow crystal powder

Uses

3,4-Dimethoxybenzonitrile is used as an organic chemical synthesis intermediate.

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 
• 91-16-7 1,2-dimethoxybenzene 
• 506-68-3 bromocyane 
• 143-33-9 sodium cyanide 
• 77-78-1 dimethyl sulfate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 13181-13-0 β-veratraldehyde-[O-(2,4-dinitro-phenyl)-oxime ] 
• 2169-98-4 3,4-Dimethoxy-benzaldehyde oxime 
• 263747-40-6 methyl iminothioveratramide 
• 1221966-45-5 ethyl 2-azido-2-(3,4-dimethoxyphenyl)acetate 

Downstream Products

• 36303-44-3 6-(3,4-dimethoxy-phenyl)-[1,3,5]triazine-2,4-diamine 
• 17345-61-8 3,4-dihydroxybenzonitrile 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 
• 60028-86-6 3,4-dimethoxy-N-methylbenzamide 
• 102714-71-6 4,5-dimethoxy-2-nitrobenzonitrile 
• 14859-20-2 {[1,1-bis(phenylthio)ethyl]thio}benzene 
• 23731-50-2 (3,4-dimethoxyphenyl)(phenyl)methylamine 
• 126520-82-9 4-(Pentyloxy)-β-3,4-(dimethoxy)phenylbenzenepropanamine 
• 69241-43-6 2-(3,4-Dimethoxybenzoyl)furan 
• 80235-75-2 2-phenyl-1-(3,4-dimethoxyphenyl)ethyl amine 
• 1222098-15-8 1-(3,4-dimethoxyphenyl)cyclopentylamine hydrochloride 
• 1245744-65-3 C₁₀H₁₁NO₂S 
• 13602-19-2 ethyl 3,4-dimethoxybenzimidate hydrochloride 
• 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.

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.