5653-62-3

Basic information

• Product Name: 2,3-DIMETHOXYBENZONITRILE
• Synonyms: O-VERATRONITRILE;BENZONITRILE, 2,3-DIMETHOXY-;LABOTEST-BB LT00159775;2,3-DIMETHOXYBENZONITRILE;2-VERATRONITRILE;3,2-DIMETHOXYBENZONITRILE;3-CYANOVERATROLE;2,3-dimethoxy-benzonitril
• CAS NO: 5653-62-3
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 227-097-4
• Product Categories: Aromatic Nitriles
• Mol File: 5653-62-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 43-46 °C(lit.)
• Boiling Point: 265℃
• Flash Point: >230 °F
• Appearance: white crystals
• Density: 1.12
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Stability: Stable. Incompatible with strong bases, strong acids, strong oxidizing agents.
• BRN: 2719631
• CAS DataBase Reference: 2,3-DIMETHOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHOXYBENZONITRILE(5653-62-3)
• EPA Substance Registry System: 2,3-DIMETHOXYBENZONITRILE(5653-62-3)

Safety Data

• Hazard Codes: Xn,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: 5653-62-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

Uses

It is employed in the replacement of nuclear alkoxyl groups to yield dimethoxy ketones by the action of methyl and phenyl Grignard reagents on 2,3-dimethoxybenzonitrile.

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

Synthetic route

oxime of 2,3-dimethoxy-benzaldehyde (5470-95-1) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 3h;	96%
With diethyl phosphorylchloridite In chloroform at 60℃; for 6h;	95%
With ammonium thiocyanate; fluorescein sodium salt In acetonitrile at 20℃; for 10h; Irradiation;	93%

2,3-dimethyoxybenzaldehyde (86-51-1) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
With PhNHCO2NH2*TsOH In toluene for 0.5h; Condensation; elimination; Heating;	93%
With hydroxylamine hydrochloride; iron(II) sulfate In N,N-dimethyl-formamide for 5h; Reflux;	90%
Multi-step reaction with 2 steps 1: (NH2OH)2*H2SO4; sodium acetate / ethanol / Heating 2: SOCl2 / benzene / Heating View Scheme
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; trimethylsilylazide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20 - 50℃; for 3h; Schmidt Reaction; Sonication;	100 %Spectr.
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; potassium acetate / water; ethanol / 0 - 20 °C 2: ruthenium trichloride; toluene-4-sulfonic acid / N,N-dimethyl acetamide; water / 8 h / 120 °C / 760.05 Torr / Inert atmosphere; Green chemistry View Scheme

O-phenylcarbamoyl-2,3-dimethoxybenzaldoxime → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 0.5h; Elimination; Heating;	92%

tert-butyl isocyanide (630-18-2) + 1,2-dimethoxybenzene (91-16-7) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
Stage #1: 1,2-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Inert atmosphere; Stage #2: tert-butyl isocyanide In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Inert atmosphere; Further stages;	91%

1,2-dimethoxybenzene (91-16-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
Stage #1: 1,2-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0℃; for 2h; Stage #3: With ammonia; iodine In tetrahydrofuran; hexane; water at 0 - 20℃;	76%
Stage #1: 1,2-dimethoxybenzene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0℃; for 2h; Stage #3: With ammonia; iodine In tetrahydrofuran; hexane; water at 0 - 20℃; for 2h;	76%

2,3-dimethoxybenzamide (1521-39-7) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
With pyridine; trichlorophosphate
With trichlorophosphate In toluene at 30 - 85℃; Temperature;
With trichlorophosphate In toluene at 30 - 85℃;

oxime of 2,3-dimethoxy-benzaldehyde (5470-95-1) + sodium acetate (127-09-3) + acetic anhydride (108-24-7) → 2,3-dimethoxybenzonitrile (5653-62-3)

2-Hydroxy-3-methoxybenzonitrile (6812-16-4) + dimethyl sulfate (77-78-1) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
With potassium carbonate In acetone Yield given;

2,3-dimethyoxybenzaldehyde (86-51-1) + butanedione-mono-<(E?)-O-methyl oxime > → 2,3-dimethoxybenzonitrile (5653-62-3) + 3.4-dihydro-naphthyl-(2)-magnesium bromide

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / ethanol / 1 h / 20 °C 2: 92 percent / TsOH*H2O / toluene / 0.5 h / Heating View Scheme

3-methoxy-2-hydroxybenzaldehyde (148-53-8) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride, HCOONa, HCOOH / 1 h / Heating 2: K2CO3 / acetone View Scheme

2,3-dimethoxybenzoyl chloride (7169-06-4) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / dichloromethane; water / 0.5 h / -5 - 35 °C 2: trichlorophosphate / toluene / 30 - 85 °C View Scheme

2,3-dimethoxybenzoic acid (1521-38-6) → 2,3-dimethoxybenzonitrile (5653-62-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2 h / 30 - 35 °C 2: ammonium hydroxide / dichloromethane; water / 0.5 h / -5 - 35 °C 3: trichlorophosphate / toluene / 30 - 85 °C View Scheme
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2 h / 30 - 35 °C 1.2: 0.5 h / -5 - 35 °C 2.1: trichlorophosphate / toluene / 30 - 85 °C View Scheme

2,3-dimethoxybenzonitrile (5653-62-3) + isopropylmagnesium chloride (1068-55-9) → 2-isopropyl-3-methoxybenzonitrile (105041-68-7)

Conditions	Yield
In diethyl ether at 0 - 23℃; Inert atmosphere;	94%
In diethyl ether at 0 - 20℃; Inert atmosphere;	84%

2,3-dimethoxybenzonitrile (5653-62-3) + methylmagnesium bromide (75-16-1) → 2,3-dimethoxyacetophenone (38480-94-3)

Conditions	Yield
Stage #1: 2,3-dimethoxybenzonitrile; methylmagnesium bromide In diethyl ether for 16h; Inert atmosphere; Stage #2: With water; acetic acid In diethyl ether; water for 0.5h;	92.5%

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxybenzamide (1521-39-7)

Conditions	Yield
With polystyrene-triethylenetetramine anchored ruthenium(II) complex; air In water at 90℃; for 7h; Green chemistry;	90%

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dihydroxybenzonitrile (67984-81-0)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 18h;	84%
With aluminum (III) chloride; triethylamine In toluene at 30 - 75℃; for 9.5h; Reagent/catalyst;
With aluminum (III) chloride; triethylamine In toluene at 70 - 75℃; for 8h; Temperature;	56 g

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxyphenylselenocarboxamide

Conditions	Yield
Stage #1: 2,3-dimethoxybenzonitrile With woollins’ reagent In toluene for 4h; Heating; Stage #2: With water In toluene for 1h;	82%
With hydrogenchloride; selenium; sodium tetrahydroborate In pyridine; ethanol; water for 2.5h; Heating;	23%

2,3-dimethoxybenzonitrile (5653-62-3) → 5-(2,3-dimethoxyphenyl)-1H-tetrazole (255727-87-8)

Conditions	Yield
With tributyltin azide In xylene for 14h; Cycloaddition; Heating;	76%
Stage #1: 2,3-dimethoxybenzonitrile With sodium azide; zinc dibromide In water; isopropyl alcohol for 24h; Heating; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃;
With sodium azide; zinc dibromide In water; isopropyl alcohol for 24h; Heating / reflux;

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxybenzamide oxime (407610-22-4)

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In ethanol for 16h; Heating;	68%

2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-Dimethoxy-benzamidine (144650-01-1)

Conditions	Yield
With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In diethyl ether at 20℃; for 4h;	62%
With lithium hexamethyldisilazane In diethyl ether for 2h; Ambient temperature;
With n-butyllithium In hexane; dichloromethane
With n-butyllithium In hexane; dichloromethane

methyl magnesium iodide (917-64-6) + 2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxyacetophenone (38480-94-3) + 1-(2-hydroxy-3-methoxyphenyl)ethanone (703-98-0)

Conditions	Yield
In diethyl ether for 18h; Grignard reaction;	A 14.4% B 57.2%

acrylic acid n-butyl ester (141-32-2) + 2,3-dimethoxybenzonitrile (5653-62-3) → butyl (E)-3-(2-cyano-3,4-dimethoxyphenyl)acrylate

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; silver(I) acetate In acetic acid at 120℃; for 16h; Inert atmosphere; regioselective reaction;	38%

2,3-dimethoxybenzonitrile (5653-62-3) → 5-(2,3-dimethoxy-phenyl)-2H-tetrazole

Conditions	Yield
With ammonium azide; ammonium chloride; lithium chloride In N,N-dimethyl-formamide at 120 - 130℃; for 24h;	33%

2-methylnicotinic acid (3222-56-8) + 2,3-dimethoxybenzonitrile (5653-62-3) → 5-chloro-7-(2,3-dimethoxyphenyl)-[1,6]naphthyridine (1319737-69-3)

Conditions	Yield
Stage #1: 2-methylnicotinic acid With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: 2,3-dimethoxybenzonitrile In tetrahydrofuran at -78 - 20℃; Stage #3: With N,N-dimethyl-aniline; trichlorophosphate at 110℃; Inert atmosphere;	26%
Stage #1: 2-methylnicotinic acid With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: 2,3-dimethoxybenzonitrile In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #3: With N,N-dimethyl-aniline; trichlorophosphate at 110℃; Inert atmosphere;	26%

4-dibenzylamino-3-trifluoromethyl-benzonitrile (1345724-19-7) + 2,3-dimethoxybenzonitrile (5653-62-3) → dibenzyl-[4-(5-chloro-[1,6]naphthyridin-7-yl)-2-trifluoromethylphenyl]amine (1345724-22-2)

Conditions	Yield
Stage #1: 2,3-dimethoxybenzonitrile With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: 4-dibenzylamino-3-trifluoromethyl-benzonitrile In tetrahydrofuran at -78 - 20℃; Stage #3: With N,N-dimethyl-aniline; trichlorophosphate at 110℃; Inert atmosphere;	20%

n-butyl magnesium bromide (693-03-8) + 2,3-dimethoxybenzonitrile (5653-62-3) → 2-butyl-3-methoxy-benzonitrile (791137-09-2)

Conditions	Yield
With diethyl ether

methyl magnesium iodide (917-64-6) + 2,3-dimethoxybenzonitrile (5653-62-3) → 2,3-dimethoxyacetophenone (38480-94-3)

Conditions	Yield
With diethyl ether anschliessend Hydrolyse;

2,3-dimethoxybenzonitrile (5653-62-3) + tert-butylmagnesium bromide (2259-30-5) → 1-(2,3-dimethoxy-phenyl)-2,2-dimethyl-propan-1-one-imine

Conditions	Yield
With diethyl ether

2,3-dimethoxybenzonitrile (5653-62-3) + n-heptylmagnesium bromide (13125-66-1) → (2,3-dimethoxyphenyl)heptyl ketone (1854-64-4) + 2-heptyl-3-methoxy-benzonitrile (108983-63-7)

Conditions	Yield
With diethyl ether und Behandeln des Reaktionsgemisches mit wss.HCl;

2,3-dimethoxybenzonitrile (5653-62-3) + 2-naphthalenylmagnesium bromide (21473-01-8) → (2,3-dimethoxy-phenyl)-[2]naphthyl ketone

Conditions	Yield
With diethyl ether und Erhitzen des Reaktionsprodukts mit wss.HCl;

2,3-dimethoxybenzonitrile (5653-62-3) + isopropylmagnesium bromide (920-39-8) → 2-isopropyl-3-methoxybenzonitrile (105041-68-7)

Conditions	Yield
With diethyl ether Behandeln des Reaktionsgemisches mit wss. Salzsaeure;

2,3-dimethoxybenzonitrile (5653-62-3) + phenylmagnesium bromide → 2,3-dimethoxybenzophenone (93081-14-2)

Conditions	Yield
With diethyl ether und Behandeln des Reaktionsprodukts mit wss.HCl;

2,3-dimethoxybenzonitrile (5653-62-3) + phenylmagnesium bromide → 6-methoxy-[1,1'-biphenyl]-2-carbonitrile (100725-39-1)

Conditions	Yield
With diethyl ether anschliessend Behandeln mit wss. Salzsaeure;

2,3-dimethoxybenzonitrile (5653-62-3) + phenylmagnesium bromide → 3-methoxy-2-phenyl-benzophenone

Conditions	Yield
With diethyl ether und Behandeln des Reaktionsgemisches mit wss.HCl;

Upstream product

• 5470-95-1 oxime of 2,3-dimethoxy-benzaldehyde 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 630-18-2 tert-butyl isocyanide 
• 91-16-7 1,2-dimethoxybenzene 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 7169-06-4 2,3-dimethoxybenzoyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 6812-16-4 2-Hydroxy-3-methoxybenzonitrile 
• 77-78-1 dimethyl sulfate 
• 1521-39-7 2,3-dimethoxybenzamide 

Downstream Products

• 106272-58-6 2-cyclohexyl-3-methoxybenzonitrile 
• 115713-40-1 2'-hydroxy-2,3'-dimethoxychalcone 
• 115713-41-2 8,2'-dihydroxyflavone 
• 115713-42-3 8,2'-dimethoxyflavone 
• 105041-68-7 2-isopropyl-3-methoxybenzonitrile 
• 144650-01-1 2,3-Dimethoxy-benzamidine 
• 135329-23-6 2-ethyl-3-methoxy-benzoic acid amide 
• 17055-42-4 1-(2-ethyl-3-methoxy-phenyl)-propan-1-one 
• 114274-16-7 2-ethyl-3-methyloxyaniline 
• 57598-51-3 2-Ethyl-3-Methoxybenzoic Acid 
• 98954-40-6 2-ethyl-3-methoxyphenol 
• 4074-50-4 2-ethylbenzene-1,3-diol 
• 52870-68-5 2,3-dihydroxybenzophenone 
• 412297-44-0 3-methoxy-2-[2]naphthyl-benzoic acid 

Relevant articles and documents

Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions

Various aromatic nitriles could be obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

PROCESS FOR PREPARATION OF 2,3-DIHYDROXY BENZONITRILE

The present invention relates to one pot process for the preparation of 2,3-dihydroxy benzonitrile from 2,3-dialkoxy benzoic acid without prior isolation of the intermediates. Further the invention relates to the preparation of 2,3-dihydroxy benzonitrile by dealkylation of 2,3-dialkoxy benzonitrile using suitable aluminum salt-amine complex.