2,3-Dimethoxybenzonitrile supplier

Name
2,3-Dimethoxybenzonitrile
EINECS 227-097-4
CAS No. 5653-62-3
Article Data22
CAS DataBase
Density 1.12 g/cm³
Solubility Insoluble in water.
Melting Point 43-46 °C(lit.)
Formula C₉H₉NO₂
Boiling Point 264.5 °C at 760 mmHg
Molecular Weight 163.176
Flash Point 106.6 °C
Transport Information 3276
Appearance white crystals
Safety 26-36
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms o-Veratronitrile(6CI,8CI);2,3-Dimethoxybenzonitrile;NSC 27018;
PSA 42.25000
LogP 1.57548

Synthetic route

: 5470-95-1
oxime of 2,3-dimethoxy-benzaldehyde

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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%

: 86-51-1
2,3-dimethyoxybenzaldehyde

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 630-18-2
tert-butyl isocyanide

: 91-16-7
1,2-dimethoxybenzene

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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%

: 91-16-7
1,2-dimethoxybenzene

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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%

: 1521-39-7
2,3-dimethoxybenzamide

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 5470-95-1
oxime of 2,3-dimethoxy-benzaldehyde

: 127-09-3
sodium acetate

: 108-24-7
acetic anhydride

: 5653-62-3
2,3-dimethoxybenzonitrile

...Expand

: 6812-16-4
2-Hydroxy-3-methoxybenzonitrile

: 77-78-1
dimethyl sulfate

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

Conditions	Yield
With potassium carbonate In acetone Yield given;

: 86-51-1
2,3-dimethyoxybenzaldehyde

butanedione-mono-<(E?)-O-methyl oxime >: butanedione-mono-<(E?)-O-methyl oxime >

A: 5653-62-3
2,3-dimethoxybenzonitrile

B 3.4-dihydro-naphthyl-(2)-magnesium bromide: 3.4-dihydro-naphthyl-(2)-magnesium bromide

Conditions

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

...Expand

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 7169-06-4
2,3-dimethoxybenzoyl chloride

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 1521-38-6
2,3-dimethoxybenzoic acid

: 5653-62-3
2,3-dimethoxybenzonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 1068-55-9
isopropylmagnesium chloride

: 105041-68-7
2-isopropyl-3-methoxybenzonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 75-16-1
methylmagnesium bromide

: 38480-94-3
2,3-dimethoxyacetophenone

Conditions

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%

: 5653-62-3
2,3-dimethoxybenzonitrile

: 1521-39-7
2,3-dimethoxybenzamide

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 67984-81-0
2,3-dihydroxybenzonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 2,3-dimethoxyphenylselenocarboxamide

Conditions

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%

: 5653-62-3
2,3-dimethoxybenzonitrile

: 255727-87-8
5-(2,3-dimethoxyphenyl)-1H-tetrazole

Conditions

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;

: 5653-62-3
2,3-dimethoxybenzonitrile

: 407610-22-4
2,3-dimethoxybenzamide oxime

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 144650-01-1
2,3-Dimethoxy-benzamidine

Conditions

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

: 917-64-6
methyl magnesium iodide

: 5653-62-3
2,3-dimethoxybenzonitrile

A: 38480-94-3
2,3-dimethoxyacetophenone

B: 703-98-0
1-(2-hydroxy-3-methoxyphenyl)ethanone

Conditions

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

...Expand

: 141-32-2
acrylic acid n-butyl ester

: 5653-62-3
2,3-dimethoxybenzonitrile

: butyl (E)-3-(2-cyano-3,4-dimethoxyphenyl)acrylate

Conditions

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%

: 5653-62-3
2,3-dimethoxybenzonitrile

: 5-(2,3-dimethoxy-phenyl)-2H-tetrazole

Conditions

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

: 3222-56-8
2-methylnicotinic acid

: 5653-62-3
2,3-dimethoxybenzonitrile

: 1319737-69-3
5-chloro-7-(2,3-dimethoxyphenyl)-[1,6]naphthyridine

Conditions

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%

: 1345724-19-7
4-dibenzylamino-3-trifluoromethyl-benzonitrile

: 5653-62-3
2,3-dimethoxybenzonitrile

: 1345724-22-2
dibenzyl-[4-(5-chloro-[1,6]naphthyridin-7-yl)-2-trifluoromethylphenyl]amine

Conditions

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%

: 693-03-8
n-butyl magnesium bromide

: 5653-62-3
2,3-dimethoxybenzonitrile

: 791137-09-2
2-butyl-3-methoxy-benzonitrile

Conditions

Conditions	Yield
With diethyl ether

: 917-64-6
methyl magnesium iodide

: 5653-62-3
2,3-dimethoxybenzonitrile

: 38480-94-3
2,3-dimethoxyacetophenone

Conditions

Conditions	Yield
With diethyl ether anschliessend Hydrolyse;

: 5653-62-3
2,3-dimethoxybenzonitrile

: 2259-30-5
tert-butylmagnesium bromide

: 1-(2,3-dimethoxy-phenyl)-2,2-dimethyl-propan-1-one-imine

Conditions

Conditions	Yield
With diethyl ether

: 5653-62-3
2,3-dimethoxybenzonitrile

: 13125-66-1
n-heptylmagnesium bromide

A: 1854-64-4
(2,3-dimethoxyphenyl)heptyl ketone

B: 108983-63-7
2-heptyl-3-methoxy-benzonitrile

Conditions

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

...Expand

: 5653-62-3
2,3-dimethoxybenzonitrile

: 21473-01-8
2-naphthalenylmagnesium bromide

: (2,3-dimethoxy-phenyl)-[2]naphthyl ketone

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: 920-39-8
isopropylmagnesium bromide

: 105041-68-7
2-isopropyl-3-methoxybenzonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: phenylmagnesium bromide

: 93081-14-2
2,3-dimethoxybenzophenone

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: phenylmagnesium bromide

: 100725-39-1
6-methoxy-[1,1'-biphenyl]-2-carbonitrile

Conditions

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

: 5653-62-3
2,3-dimethoxybenzonitrile

: phenylmagnesium bromide

: 3-methoxy-2-phenyl-benzophenone

Conditions

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

2,3-Dimethoxybenzonitrile Specification

The CAS register number of 2,3-Dimethoxybenzonitrile is 5653-62-3. It also can be called as o-Veratronitrile and the IUPAC name about this chemical is 2,3-dimethoxybenzonitrile. The molecular formula about this chemical is C₉H₉NO₂ and the molecular weight is 163.17. It belongs to the Aromatic Nitriles.

Physical properties about 2,3-Dimethoxybenzonitrile are: (1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): 1.57; (3)ACD/LogD (pH 7.4): 1.57; (4)ACD/BCF (pH 5.5): 9.17; (5)ACD/BCF (pH 7.4): 9.17; (6)ACD/KOC (pH 5.5): 170.01; (7)ACD/KOC (pH 7.4): 170.01; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 42.25Å²; (11)Index of Refraction: 1.519; (12)Molar Refractivity: 44.05 cm³; (13)Molar Volume: 144.9 cm³; (14)Polarizability: 17.46x10^-24cm³; (15)Surface Tension: 42.5 dyne/cm; (16)Enthalpy of Vaporization: 50.24 kJ/mol; (17)Boiling Point: 264.5 °C at 760 mmHg; (18)Vapour Pressure: 0.00966 mmHg at 25°C.

Preparation: this chemical can be prepared by 2,3-dimethoxy-benzaldehyde-oxime. This reaction will need reagent diethyl chlorophosphite and solvent CHCl₃. The reaction time is 6 hour(s) with reaction temperature of 60 ℃. The yield is about 95%.

Uses of 2,3-Dimethoxybenzonitrile: it can be used to produce 2,3-dimethoxy-benzamidine at temperature of 20 ℃. This reaction will need reagent 1,1,1,3,3,3-hexamethyldisilazane, BuLi and solvent diethyl ether with reaction time of 4 hour(s). The yield is about 62%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: N#Cc1cccc(OC)c1OC
(2)InChI: InChI=1/C9H9NO2/c1-11-8-5-3-4-7(6-10)9(8)12-2/h3-5H,1-2H3
(3)InChIKey: LBXGBNHUNHWYRM-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C9H9NO2/c1-11-8-5-3-4-7(6-10)9(8)12-2/h3-5H,1-2H3
(5)Std. InChIKey: LBXGBNHUNHWYRM-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	56mg/kg (56mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04768,

Product Name

2,3-Dimethoxybenzonitrile

Synthetic route

2,3-Dimethoxybenzonitrile Specification

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