4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 1-(6-amino-2-bromo-3,4-dimethoxyphenyl)ethan-1-one With 1 ,5-pentanediol for 0.666667h; Stage #2: With nickel(III) oxide; potassium carbonate at 70℃; for 0.666667h; pH=9; Temperature; pH-value; | 96% |
2-nitroveratraldehyde
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With sodium chlorite; dihydrogen peroxide; acetic acid In methanol; water at 50℃; Solvent; Temperature; Concentration; Reagent/catalyst; | 93% |
Stage #1: 6-nitroveratraldehyde With potassium dihydrogenphosphate In water; acetonitrile Stage #2: With sodium chlorite In water; acetonitrile at 25 - 35℃; | 88% |
With potassium permanganate; sodium hydroxide for 7h; | 83% |
Conditions | Yield |
---|---|
With nitric acid; acetic acid at 90℃; under 11251.1 Torr; for 0.0833333h; Temperature; Pressure; Flow reactor; | 87.6% |
With nitric acid In water at 60℃; for 6h; Cooling with ice; | 77% |
With nitric acid at 60℃; for 6.5h; Cooling with ice; | 77% |
4,5-dimethoxy-2-nitro-benzoic acid
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
Oxydation; |
Veratric acid
A
3,4-dimethoxynitrobenzene
B
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With nitric acid |
2-(4,5-dimethoxy-2-nitro-phenyl)-3,5,7-trimethoxy-chromen-4-one
4,5-dimethoxy-2-nitro-benzoic acid
4,5-dimethoxy-2-nitro-benzoic acid
nitric acid
Veratric acid
A
3,4-dimethoxynitrobenzene
B
4,5-dimethoxy-2-nitro-benzoic acid
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With ethanol |
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With potassium permanganate |
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With potassium permanganate; water |
14-nitro-N-methylpapaverinium iodide
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
at 100℃; |
(4,5-dimethoxy-2-methyl-3-nitro-phenyl)-hydrazine
copper(II) sulfate
acetic acid
A
4,5-dimethoxy-2-nitro-benzoic acid
B
3,4-Dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
Oxydation des entstandenen Oels mit Permanganat; |
methyl 4,5-dimethoxy-2-nitrobenzoate
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran | |
With sodium hydroxide In methanol | |
Stage #1: methyl 4,5-dimethoxy-2-nitrobenzoate With potassium hydroxide; water at 0 - 70℃; Heating / reflux; Stage #2: With acetic acid In water at 20℃; pH=6.6; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: K2CO3 / acetone / Heating 2: HNO3; acetic acid / 50 - 60 °C 3: NaOH / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2SO4 / Heating 2: K2CO3 / acetone / Heating 3: HNO3; acetic acid / 50 - 60 °C 4: NaOH / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HNO3; acetic acid / 50 - 60 °C 2: NaOH / tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 3: KMnO4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: KMnO4 View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid / 5 - 10 °C 2: KOH-solution; KMnO4 View Scheme | |
Multi-step reaction with 2 steps 1: nitric acid / 1 h / 20 - 25 °C 2: sodium hydroxide; potassium permanganate / 7 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water; KMnO4 / 80 - 90 °C 2: nitric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetic anhydride; nitric acid / 6 h / 0 - 20 °C 2: potassium permanganate; copper(ll) sulfate pentahydrate; potassium hydroxide / benzene / 10 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With potassium permanganate; copper(ll) sulfate pentahydrate; potassium hydroxide In benzene for 10h; Reflux; | 13 g |
4,5-dimethoxy-2-nitro-benzoic acid
4,5-dimethoxy-2-nitrobenzoyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In toluene for 3h; Heating; | 100% |
With phosphorus pentachloride | |
With thionyl chloride; chloroform |
4,5-dimethoxy-2-nitro-benzoic acid
2-(4-aminophenyl)-2-methylpropionitrile
N-[4-(cyano-dimethyl-methyl)-phenyl]-4,5-dimethoxy-2-nitro-benzamide
Conditions | Yield |
---|---|
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; Stage #2: 2-(4-aminophenyl)-2-methylpropionitrile With triethylamine In dichloromethane at 20℃; | 100% |
Conditions | Yield |
---|---|
With silver carbonate In dimethyl sulfoxide at 120℃; for 16h; | 100% |
With copper(l) iodide; triethylamine In dimethyl sulfoxide at 140℃; under 760.051 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | 95% |
4,5-dimethoxy-2-nitro-benzoic acid
potassium 2-nitro-4,5-dimethoxybenzoate
Conditions | Yield |
---|---|
With potassium tert-butylate In ethanol at 20℃; for 3h; Inert atmosphere; | 100% |
4,5-dimethoxy-2-nitro-benzoic acid
2-nitro-4-methoxy-5-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With sodium hydroxide; water at 100℃; for 3h; Stage #2: With hydrogenchloride In water at 0℃; pH=< 2; | 99% |
With water; sodium hydroxide at 100℃; for 3h; Inert atmosphere; | 99% |
With water; sodium hydroxide at 100℃; for 6h; | 97.6% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 7600.51 Torr; for 6h; | 97% |
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h; | 92% |
With hydrazine hydrate In ethanol at 60℃; for 5h; Sealed tube; Green chemistry; chemoselective reaction; | 87% |
4,5-dimethoxy-2-nitro-benzoic acid
Conditions | Yield |
---|---|
With dmap; copper diacetate In acetonitrile at 100℃; for 6h; Schlenk technique; Sealed tube; Inert atmosphere; | 94% |
4,5-dimethoxy-2-nitro-benzoic acid
N,N-dimethyl-formamide
N,N-dimethyl-4,5-dimethoxy-2-nitrobenzamide
Conditions | Yield |
---|---|
With trichlorophosphate at 120℃; for 1h; Sealed tube; | 93% |
With trichlorophosphate at 120℃; for 1h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With thionyl chloride for 0.833333h; Heating; Stage #2: With ammonium hydroxide | 88.5% |
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With triethylamine; Diphenylphosphinic chloride In chloroform Stage #2: With ammonia | |
Multi-step reaction with 2 steps 1: SOCl2 2: NH4OH View Scheme |
Conditions | Yield |
---|---|
With triethylamine In acetone for 1.5h; | 86% |
Conditions | Yield |
---|---|
In methanol; water at 20℃; | 86% |
4,5-dimethoxy-2-nitro-benzoic acid
1-(4,5-dimethoxy-2-nitrobenzoyl)-4-hydroxypyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 16h; Stage #2: (2S,4R)-4-hydroxy-2-proline methyl ester 4-toluenesulfonate With triethylamine In dichloromethane at -20 - 20℃; for 16h; | 85% |
With oxalyl dichloride; TEA In dichloromethane; N,N-dimethyl-formamide at 20℃; | 57% |
Conditions | Yield |
---|---|
With silver carbonate; palladium(II) trifluoroacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 3h; Heck olefination; | 85% |
Conditions | Yield |
---|---|
With triethanolamine; N,N-dimethyl-formamide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran | 85% |
4,5-dimethoxy-2-nitro-benzoic acid
Diphenyliodonium triflate
4,5-dimethoxy-2-nitrobiphenyl
Conditions | Yield |
---|---|
With silver carbonate; bis[2-(diphenylphosphino)phenyl] ether; palladium dichloride In dimethyl sulfoxide at 150℃; for 1h; | 85% |
Conditions | Yield |
---|---|
With oxygen; silver carbonate; potassium hydroxide; copper dichloride In dimethyl sulfoxide; N,N-dimethyl-formamide at 130 - 140℃; | 85% |
With copper(l) iodide; oxygen; copper(l) chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 30h; Schlenk technique; Sealed tube; | 65% |
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper (I) acetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; for 24h; Schlenk technique; | 52% |
With 2.9-dimethyl-1,10-phenanthroline; oxygen; copper diacetate; silver sulfate; sodium chloride In dimethyl sulfoxide at 160℃; under 760.051 Torr; for 20h; Schlenk technique; | 52% |
iodobenzene
4,5-dimethoxy-2-nitro-benzoic acid
4,5-dimethoxy-2-nitrobiphenyl
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-aniline; silver carbonate; palladium dichloride at 150℃; for 2h; | 82% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification; | 82% |
4,5-dimethoxy-2-nitro-benzoic acid
3-hydroxy-2-methyl-1-propene
2-methylallyl 4,5-dimethoxy-2-nitrobenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification; | 82% |
2-bromobenzoic acid methyl ester
4,5-dimethoxy-2-nitro-benzoic acid
2,3-dimethoxydibenzopyran-6-one
Conditions | Yield |
---|---|
With palladium(II) acetylacetonate; potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether; copper(l) chloride In 1-methyl-pyrrolidin-2-one at 165℃; for 16h; Inert atmosphere; Molecular sieve; chemoselective reaction; | 81% |
4,5-dimethoxy-2-nitro-benzoic acid
dioctyltin(IV) oxide
n-Oct2Sn(4,5-dimethoxy-2-nitrobenzoate)2
Conditions | Yield |
---|---|
In toluene byproducts: H2O; Stoich. amounts of HL and n-Oct2SO were mixed in toluene, reflux for 6-7h, H2O was removed using a Dean-Stark apparatus; Toluene was evapd. under reduced pressure, mass was crystd. from CHCl3:acetone (1:1); elem. anal.; | 80% |
4,5-dimethoxy-2-nitro-benzoic acid
tributyltin chloride
n-Bu3Sn(4,5-dimethoxy-2-nitrobenzoate)
Conditions | Yield |
---|---|
With Et3N In chloroform byproducts: Et3NHCl; Et3N (1 mmol) was added to dissolved in solvent HL (1 mmol), mixt. was refluxed 30 min, 1 mmol n-Bu3SnCl was added, solution was refluxed for 4-7 h, mixt. was kept at 25°C overnight; Et3NHCl was filtered off, solvent was evapd. under redused pressure, mass was crystd. from CHCL3:n-hexane (1:1); elem. anal; | 80% |
4,5-dimethoxy-2-nitro-benzoic acid
triphenyltin chloride
Ph3Sn(4,5-dimethoxy-2-nitrobenzoate)
Conditions | Yield |
---|---|
With Et3N In chloroform byproducts: Et3NHCl; Et3N (1 mmol) was added to dissolved in solvent HL (1 mmol), mixt. was refluxed 30 min, 1 mmol n-Bu3SnCl was added, solution was refluxed for 4-7 h, mixt. was kept at 25°C overnight.; Et3NHCl was filtered off, solvent was evapd. under redused pressure, mass was crystd. from CHCl3:n-hexane (1:1); elem. anal; | 80% |
4,5-dimethoxy-2-nitro-benzoic acid
4,4',5,5'-tetramethoxy-2,2'-dinitro-1,1'-biphenyl
Conditions | Yield |
---|---|
With triphenylphosphine; silver carbonate; palladium dichloride In dimethyl sulfoxide at 130℃; for 6h; Inert atmosphere; | 80% |
(E)-p-methoxy-cinnamyl alcohol
4,5-dimethoxy-2-nitro-benzoic acid
4-methoxycinnamyl 4,5-dimethoxy-2-nitrobenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification; | 80% |
(2S,4R)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine
4,5-dimethoxy-2-nitro-benzoic acid
(2S)(4R)-N-(4,5-dimethoxy-2-nitrobenzoyl)-2-(tert-butyldimethylsilyloxymethyl)-4-oxyacetylpyrrolidine
Conditions | Yield |
---|---|
Stage #1: 4,5-dimethoxy-2-nitro-benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide); dichloromethane at 0 - 20℃; for 1h; Stage #2: (2S,4R)-2-t-butyldimethylsilyloxymethyl-4-oxyacetylpyrrolidine In dichloromethane at 20 - 55℃; for 18h; | 79.9% |
Conditions | Yield |
---|---|
With triphenyl-arsane; silver carbonate; palladium dichloride In dimethyl sulfoxide at 150℃; for 6h; | 79% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N,N-dimethyl-aniline; silver carbonate; palladium dichloride at 150℃; for 2h; | 72% |
Molecule structure of 4,5-Dimethoxy-2-nitrobenzoic acid (CAS NO.4998-07-6) :
IUPAC Name: 4,5-dimethoxy-2-nitrobenzoic acid
Molecular Weight: 227.17086 g/mol
Molecular Formula: C9H9NO6
Density: 1.403 g/cm3
Melting Point: 195-197 °C(lit.)
Boiling Point: 409.5 °C at 760 mmHg
Flash Point: 201.4 °C
Appreance: yellow crystalline powder
Molar Volume: 161.8 cm3
Polarizability: 21.04*10-24 cm3
Surface Tension: 53.7 dyne/cm
Enthalpy of Vaporization: 69.77 kJ/mol
Vapour Pressure: 1.94E-07 mmHg at 25 °C
log P (octanol-water): 0.990
Water Solubility: 4.00E+04 mg/L
Atmospheric OH Rate Constant: 2.81E-12 cm3/molecule-sec
XLogP3-AA: 1.2
H-Bond Donor: 1
H-Bond Acceptor: 6
Rotatable Bond Count: 3
Exact Mass: 227.042987
MonoIsotopic Mass: 227.042987
Topological Polar Surface Area: 98.9
Heavy Atom Count: 16
Complexity: 276
Canonical SMILES: COC1=C(C=C(C(=C1)C(=O)O)[N+](=O)[O-])OC
InChI: InChI=1S/C9H9NO6/c1-15-7-3-5(9(11)12)6(10(13)14)4-8(7)16-2/h3-4H,1-2H3,(H,11,12)
InChIKey: WWCMFGBGMJAJRX-UHFFFAOYSA-N
EINECS: 225-657-2
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic acids; Aromatics; C9; Carbonyl Compounds; Carboxylic Acids
4,5-Dimethoxy-2-nitrobenzoic acid (CAS NO.4998-07-6) is used as pharmaceutical intermediate, mainly used to be prazosin hydrochloride intermediate.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3
4,5-Dimethoxy-2-nitrobenzoic acid (CAS NO.4998-07-6) is also called 6-Nitroveratriceacid ; Rarechem AL BO 1523 ; 2-Nitro-4,5-dimethoxybenzoic acid ; 6-Nitroveratric acid ; 3,4-Dimethoxy-6-nitrobenzoic acid ; 6-Nitroveratricacid,99% .
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