4992-63-6

Basic information

• Product Name: 3,4-DIETHOXY NITROBENZENE
• Synonyms: 3,4-DIETHOXY NITROBENZENE;1,2-Diethoxy-4-nitrobenzene;Benzene, 1,2-diethoxy-4-nitro-;MFCD00186132
• CAS NO: 4992-63-6
• Molecular Formula: C₁₀H₁₃NO₄
• Molecular Weight: 211.22
• Mol File: 4992-63-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 75 °C
• Boiling Point: 328.6°C at 760 mmHg
• Flash Point: 145.8°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 0.000358mmHg at 25°C
• Refractive Index: 1.52
• CAS DataBase Reference: 3,4-DIETHOXY NITROBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIETHOXY NITROBENZENE(4992-63-6)
• EPA Substance Registry System: 3,4-DIETHOXY NITROBENZENE(4992-63-6)

Safety Data

• Hazardous Substances Data: 4992-63-6(Hazardous Substances Data)

Usage

General Description

3,4-diethoxy nitrobenzene is a compound with the molecular formula C10H13NO4. It is a pale yellow, solid substance with a slightly sweet odor. This chemical is used in the production of pharmaceuticals and organic synthesis. It is also used as an intermediate in the manufacture of dyes, pigments, and agrochemicals. 3,4-diethoxy nitrobenzene is considered to be harmful if swallowed, inhaled, or absorbed through the skin, and it may cause irritation to the eyes and skin. It is important to handle this chemical with care and to use proper protective equipment when working with it.

InChI:InChI=1/C10H13NO4/c1-3-14-9-6-5-8(11(12)13)7-10(9)15-4-2/h5-7H,3-4H2,1-2H3

Synthetic route

1,2-dihydroxy-4-nitrobenzene (3316-09-4) + ethyl iodide (75-03-6) → 1,2-diethoxy-4-nitrobenzene (4992-63-6)

Conditions	Yield
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 12h;	95.6%
Stage #1: 1,2-dihydroxy-4-nitrobenzene With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; Stage #2: ethyl iodide at 0 - 20℃; for 12h;	76%
With sodium hydride In 1,4-dioxane
Stage #1: 1,2-dihydroxy-4-nitrobenzene With sodium hydride In N,N-dimethyl-formamide at 50℃; for 0.75h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 50℃; for 2h;

1,2-diethoxybenzene (2050-46-6) → 1,2-diethoxy-4-nitrobenzene (4992-63-6)

Conditions	Yield
With Montmorillonite KSF; nitric acid; hafnium oxychloride In tetrahydrofuran at 20℃; for 18h;	92%
With Yb-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;	66%
With nitric acid; acetic acid
(nitration);

2-Ethoxyphenol (94-71-3) → 1,2-diethoxy-4-nitrobenzene (4992-63-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcoholic KOH-solution 2: glacial acetic acid; nitric acid View Scheme

benzene-1,2-diol (120-80-9) + 1,2-bis<2-(-p-toluenesulfonyloxy)ethoxy>amine → 1,2-diethoxy-4-nitrobenzene (4992-63-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / 2-methoxy-ethanol 2: (nitration) View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 2-Ethoxy-4-nitrophenol K-Salt (113489-36-4)

Conditions	Yield
With potassium hydroxide In water for 9h; Heating;	98%

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 3,4-diethoxyaniline (39052-12-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol for 6h;	92.9%
With sodium sulfide

methanol (67-56-1) + 1,2-diethoxy-4-nitrobenzene (4992-63-6) → 2-ethoxy-4-nitroanisole (36160-52-8)

Conditions	Yield
With sodium hydroxide at 100℃;

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 1,2-diethoxy-4,5-dinitrobenzene (40294-27-7)

Conditions	Yield
With nitric acid
With ammonium nitrate; sulfuric acid In acetic acid

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 3-ethoxy-4-hydroxynitrobenzene (40130-25-4)

Conditions	Yield
With sodium hydroxide
With potassium hydroxide In 2-methoxy-ethanol Heating;
Stage #1: 4-Nitro-1,2-diethoxybenzene With water; potassium hydroxide In 2-methoxy-ethanol for 18h; Reflux; Stage #2: With hydrogenchloride In water pH=1;

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 2-ethoxy-5-nitro-phenol (7260-32-4)

Conditions	Yield
With hydrogen bromide; acetic acid

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 3,4-diethoxyphenol (65383-59-7)

Conditions	Yield
With hydrogenchloride; tin Diazotieren und Zersetzen;

1,2-diethoxy-4-nitrobenzene (4992-63-6) → N-(3,4-diethoxy-phenyl)-diacetamide

Conditions	Yield
anschliessend Behandeln mit Essigsaeureanhydrid; durch Reduktion;

1,2-diethoxy-4-nitrobenzene (4992-63-6) + acetic anhydride (108-24-7) → 4-Acetylamino-1,2-diethoxy-5-nitrobenzene (113475-63-1)

Conditions	Yield
Yield given. Multistep reaction;

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-ethoxy-4-hydroxynitrobenzene (40130-25-4)

methanol (67-56-1) + 1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 2-ethoxy-4-nitroanisole (36160-52-8)

Conditions	Yield
at 100℃;

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-ethoxy-4-hydroxyaniline (55483-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → [3-Ethoxy-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-carbamic acid isopropyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → isopropyl 3-ethoxy-4-hydroxycarbanilate (135325-73-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-{3-ethoxy-2-hydroxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-hydroxypropionic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 5: aq. NaOH View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 2-acetoxy-3-(3-ethoxy-2-hydroxy-5-isopropoxycarbonylamino-phenylsulfanyl)-propionic acid ethyl ester (601488-03-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → isopropyl 3-ethoxy-4-(β-D-glucopyranosyl-1-oxy)carbanilate

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: CH2Cl2 5: aq. NaOH View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(2-ethoxy-4-isopropoxycarbonylamino-phenoxy)-tetrahydro-pyran-3-yl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: CH2Cl2 View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-{3-ethoxy-2-hydroxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-β-D-glucopyranosyloxypropionic acid

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 5: aq. NaOH View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-{3-ethoxy-2-β-D-glucopyranosyloxy-5-[(isopropoxycarbonyl)amino]phenylthio}-2-hydroxypropionic acid

Conditions	Yield
Multi-step reaction with 7 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 5: CH2Cl2 6: aq. NaOH View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 3-(3-Ethoxy-2-hydroxy-5-isopropoxycarbonylamino-phenylsulfanyl)-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid ethyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) + aqueous NaOH → 2-Acetoxy-3-[3-ethoxy-5-isopropoxycarbonylamino-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phenylsulfanyl]-propionic acid ethyl ester

Conditions	Yield
Multi-step reaction with 6 steps 1: aq. KOH / 2-methoxy-ethanol / Heating 2: H2 / 10 percent Pd/C 3: Me2NPh / dimethylformamide 4: Pb(OAc)4 / CH2Cl2 5: CH2Cl2 View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 4,5-Diethoxy-2-nitroaniline (113475-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: 95 percent / KOH / H2O; methanol / 0.5 h / Heating View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) → 4,5-Diethoxy-2-nitrophenyl Isocyanate (113475-68-6)

Conditions	Yield
Multi-step reaction with 3 steps 2: 95 percent / KOH / H2O; methanol / 0.5 h / Heating 3: 90 percent / xylene View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) → C27H36N4O12 (113475-72-2)

Conditions	Yield
Multi-step reaction with 4 steps 2: 95 percent / KOH / H2O; methanol / 0.5 h / Heating 3: 90 percent / xylene 4: 74 percent / dioxane / Ambient temperature View Scheme

1,2-diethoxy-4-nitrobenzene (4992-63-6) → C26H34N4O12S (113475-73-3)

Conditions	Yield
Multi-step reaction with 4 steps 2: 95 percent / KOH / H2O; methanol / 0.5 h / Heating 3: 90 percent / xylene 4: 30 percent / dioxane / Ambient temperature View Scheme

Upstream product

• 2050-46-6 1,2-diethoxybenzene 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 75-03-6 ethyl iodide 
• 94-71-3 2-Ethoxyphenol 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 113475-73-3 C₂₆H₃₄N₄O₁₂S 
• 113475-72-2 C₂₇H₃₆N₄O₁₂ 
• 113475-68-6 4,5-Diethoxy-2-nitrophenyl Isocyanate 
• 113475-65-3 4,5-Diethoxy-2-nitroaniline 
• 40130-25-4 3-ethoxy-4-hydroxynitrobenzene 
• 113475-63-1 4-Acetylamino-1,2-diethoxy-5-nitrobenzene 
• 113489-36-4 2-Ethoxy-4-nitrophenol K-Salt 
• 39052-12-5 3,4-diethoxyaniline 
• 7260-32-4 2-ethoxy-5-nitro-phenol 
• 40294-27-7 1,2-diethoxy-4,5-dinitrobenzene 
• 36160-52-8 2-ethoxy-4-nitroanisole 
• 601488-03-3 2-acetoxy-3-(3-ethoxy-2-hydroxy-5-isopropoxycarbonylamino-phenylsulfanyl)-propionic acid ethyl ester 
• 135325-73-4 isopropyl 3-ethoxy-4-hydroxycarbanilate 
• 55483-70-0 3-ethoxy-4-hydroxyaniline 

Relevant articles and documents

Nitration method for aryl phenol or aryl ether derivative

The invention relates to a nitration method for an aryl phenol or aryl ether derivative. The method comprises the steps of stirring an aryl phenol or aryl ether compound, nitrate, trimethylchlorosilane (TMSCl) and a copper salt in an acetonitrile solution in air at room temperature, simultaneously, monitoring extent of reaction through a TLC dot plate, removing a solvent from a mixture by a rotaryevaporator after a substrate is consumed completely, and carrying out purification through a silica-gel column, thereby obtaining a nitroolefin derivative. Meanwhile, the selective mono-nitration orbis-nitration of the substrate can be achieved through controlling equivalent weight of the nitrate. Compared with the prior art, the nitration method disclosed by the invention has the advantages that the consumption of strong-acid substances is avoided, the reaction conditions are mild, the yield is high, the applicable range of the substrate is wide, reaction activity is free of obvious attenuation after an amplified reaction, and an excellent yield is still obtained, so that the method has an obvious industrial application value.

Highly efficient catalytic nitration of phenolic compounds by nitric acid with a recoverable and reusable Zr or Hf oxychloride complex and KSF

Phenolic compounds can be nitrated with 60% nitric acid (1.2 equiv.) in the presence of catalytic amounts of a Zr or Hf oxychloride complex and montmorillonite KSF to give the corresponding nitrated products in good yields in a heterogeneous catalytic system. The co-catalyst and montmorillon ite can be easily recovered and reused in the next batch of nitration. This is a practical process for the nitration of phenolic compounds in a clean way. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

BENZENE DERIVATIVES,PROCESS FOR PREPARING THE SAME AND USE THEREOF

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