Benzenamine,4-ethoxy-2-nitro- supplier

Name
4-ETHOXY-2-NITROANILINE
EINECS 210-497-8
CAS No. 616-86-4
Article Data30
CAS DataBase
Density 1.264 g/cm³
Solubility
Melting Point 111-113 °C(lit.)
Formula C₈H₁₀N₂O₃
Boiling Point 346.2 °C at 760 mmHg
Molecular Weight 182.179
Flash Point 163.2 °C
Transport Information
Appearance red to rust-brown crystals or crystalline powder
Safety 26-37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn
Synonyms p-Phenetidine,2-nitro- (7CI,8CI);(4-Ethoxy-2-nitrophenyl)amine;2-Nitro-p-phenetidine;4-Amino-3-nitrophenetole;4-Ethoxy-2-nitroaniline;4-Ethoxy-2-nitrobenzenamine;NSC 1320;NSC 58160;
PSA 81.07000
LogP 2.68010

Synthetic route

: 885-81-4
N-(4-ethoxy-2-nitrophenyl)acetamide

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With methanol; sodium hydride In tetrahydrofuran at 20℃; for 6h;	83%
With hydrogenchloride
With sulfuric acid

: 156-43-4
4-Ethoxyaniline

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
Stage #1: 4-Ethoxyaniline With acetic anhydride; triethylamine In dichloromethane at 0 - 20℃; Stage #2: With nitric acid In dichloromethane at 0 - 20℃; Stage #3: With sodium hydride In tetrahydrofuran; methanol; mineral oil at 20℃;	83%
Multi-step reaction with 2 steps 1: diethyl ether; potassium ethoxide View Scheme

: 610-81-1
4-hydroxy-2-nitroaniline

: 75-03-6
ethyl iodide

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In ethanol at 60℃;	75%
With potassium carbonate In hexane; ethyl acetate; acetonitrile	50.8%

: N-nitro-p-phenetidine

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With sodium hydroxide
With sulfuric acid

: 380195-34-6
chloro-acetic acid-(4-ethoxy-2-nitro-anilide)

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With potassium hydroxide

: 329063-81-2
lactic acid-(4-ethoxy-2-nitro-anilide)

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With potassium hydroxide

: 108142-81-0
methanesulfonic acid-(4-ethoxy-2-nitro-anilide)

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With sulfuric acid

: 901285-90-3
ethanesulfonic acid-(4-ethoxy-2-nitro-anilide)

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With sulfuric acid

: 861560-26-1
2-nitro-toluene-4-sulfonic acid-(4-ethoxy-2-nitro-anilide)

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With sulfuric acid at 60 - 70℃;

: 64-17-5
ethanol

: 885-81-4
N-(4-ethoxy-2-nitrophenyl)acetamide

: 7697-37-2
nitric acid

: 616-86-4
2-nitro-4-ethoxyaniline

...Expand

nitrohydroquinone-diethyl ether: nitrohydroquinone-diethyl ether

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With ammonia; water at 130 - 140℃;

: 329063-81-2
lactic acid-(4-ethoxy-2-nitro-anilide)

alcoholic KOH-solution: alcoholic KOH-solution

: 616-86-4
2-nitro-4-ethoxyaniline

: N-nitro-p-phenetidine

aqueous NaOH-solution: aqueous NaOH-solution

: 616-86-4
2-nitro-4-ethoxyaniline

: 380195-34-6
chloro-acetic acid-(4-ethoxy-2-nitro-anilide)

diluted KOH-solution: diluted KOH-solution

: 616-86-4
2-nitro-4-ethoxyaniline

: 62-44-2
4-ethoxyacetanilide

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3; AcOH / 5 - 20 °C 2: aq. H2SO4 / 70 - 80 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid / durch allmaehliches Hinzufuegen von konz.Salpetersaeure in geringem Ueberschuss 2: alcoholic potash View Scheme
Multi-step reaction with 2 steps 1: acetic acid; nitric acid / <12 2: diluted aqueous hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: alcohol; nitric acid / <25 / anschliessendes kurzes Erwaermen auf 40-60grad 2: alcohol; nitric acid View Scheme
Multi-step reaction with 2 steps 1: acetic acid; nitric acid 2: aq.-ethanolic NaOH-solution View Scheme

: 10406-66-3
methanesulfonic acid p-phenetidide

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; nitric acid 2: concentrated sulfuric acid View Scheme
Multi-step reaction with 2 steps 1: alcohol; nitric acid 2: concentrated sulfuric acid View Scheme

: 349099-73-6
2-nitro-toluene-4-sulfonic acid p-phenetidide

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; nitric acid 2: concentrated sulfuric acid / 60 - 70 °C View Scheme
Multi-step reaction with 2 steps 1: glacial acetic acid; nitric acid / 14 - 24 °C 2: concentrated sulfuric acid / 60 - 70 °C View Scheme

: 74-96-4
ethyl bromide

: 610-81-1
4-hydroxy-2-nitroaniline

: 616-86-4
2-nitro-4-ethoxyaniline

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 52h;

: 463-71-8
thiophosgene

: 616-86-4
2-nitro-4-ethoxyaniline

: 87200-45-1
4-ethoxy-2-nitro-phenyl isothiocyanate

Conditions

Conditions	Yield
In ethyl acetate at 75℃; for 1h;	97%
With water
With hydrogenchloride; acetic acid In chloroform Yield given;

: 71-23-8
propan-1-ol

: 616-86-4
2-nitro-4-ethoxyaniline

: 5-ethoxy-2-ethylbenzimidazole

Conditions

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	96%

: 616-86-4
2-nitro-4-ethoxyaniline

: 555-16-8
4-nitrobenzaldehdye

: 762-04-9
phosphonic acid diethyl ester

: 1263200-41-4
[(4-ethoxy-2-nitrophenylamino)-(4-nitrophenyl)-methyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With niobium pentachloride at 60℃; for 0.583333h; Kabachnik-Fields reaction; neat (no solvent);	95%

...Expand

: 64-17-5
ethanol

: 616-86-4
2-nitro-4-ethoxyaniline

: 5895-31-8
5-ethoxy-2-methyl-1(3)H-benzoimidazole

Conditions

Conditions	Yield
With titanium(IV) oxide for 4h; Irradiation;	94%

: 616-86-4
2-nitro-4-ethoxyaniline

: 762-04-9
phosphonic acid diethyl ester

: 552-89-6
2-nitro-benzaldehyde

: 1308428-35-4
[(4-ethoxy-3-nitrophenylamino)-(2-nitrophenyl)-methyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With xanthan sulfuric acid at 60℃; for 1h; Neat (no solvent);	93%

...Expand

: 616-86-4
2-nitro-4-ethoxyaniline

: 99-61-6
3-nitro-benzaldehyde

: 762-04-9
phosphonic acid diethyl ester

: 1263200-42-5
[(4-ethoxy-2-nitrophenylamino)-(3-nitrophenyl)-methyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With niobium pentachloride at 60℃; for 0.833333h; Kabachnik-Fields reaction; neat (no solvent);	86%

...Expand

: 1446338-09-5
2-(3-ethoxyphenoxy)acetyl chloride

: 616-86-4
2-nitro-4-ethoxyaniline

: 1446338-10-8
N-(4-ethoxy-2-nitrophenyl)-2-(3-ethoxyphenoxy)acetamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	80%

: 616-86-4
2-nitro-4-ethoxyaniline

(halomethyl)benzene: (halomethyl)benzene

: N-benzyl-4-ethoxy-2-nitroaniline

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 70℃; for 6h;	78.9%

: 616-86-4
2-nitro-4-ethoxyaniline

: 3840-30-0
5-(chloromethyl)-1,2,3-trimethoxybenzene

: 4-ethoxy-2-nitro-N-(3,4,5-trimethoxybenzyl)aniline

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile at 70℃; for 6h;	75.3%

: 616-86-4
2-nitro-4-ethoxyaniline

: 645-45-4
hydrocinnamic acid chloride

: 353783-49-0
N-(4-ethoxy-2-nitrophenyl)-3-phenylpropanamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	70%

: 616-86-4
2-nitro-4-ethoxyaniline

: 122-01-0
4-chloro-benzoyl chloride

: 4-Chloro-N-(4-ethoxy-2-nitrophenyl)-benzoylamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran Heating;	57%

: 98-98-6
2-Picolinic acid

: 616-86-4
2-nitro-4-ethoxyaniline

: N-(4-Ethoxy-2-nitrophenyl)-2-pyridinecarboxamide

Conditions

Conditions	Yield
Stage #1: 2-Picolinic acid With 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 20℃; Stage #2: 2-nitro-4-ethoxyaniline With triethylamine In tetrahydrofuran Heating;	52%

: 58757-38-3
6-Chloronicotinoyl chloride

: 616-86-4
2-nitro-4-ethoxyaniline

: 352228-42-3
6-chloro-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran Heating;	34%

: 3222-47-7
6-methylnicotinic acid

: 616-86-4
2-nitro-4-ethoxyaniline

: 6-Methyl-N-(4-ethoxy-2-nitrophenyl)-3-pyridinecarboxamide

Conditions

Conditions	Yield
Stage #1: 6-methylnicotinic acid With 1,3,5-trichloro-2,4,6-triazine In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-nitro-4-ethoxyaniline With triethylamine In tetrahydrofuran for 20h; Heating;	32%

: 616-86-4
2-nitro-4-ethoxyaniline

: 61098-38-2
5,7-dichloro-6-methylpyrazolo[1,5-a]pyrimidine

: 5-chloro-N-(4-ethoxy-2-nitrophenyl)-6-methylpyrazolo[1,5-a]pyrimidin-7-amine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 70℃; for 4h;	32%

: 61672-69-3
5-ethylisoxazole-3-carbonyl azide

: 616-86-4
2-nitro-4-ethoxyaniline

: N-(4-ethoxy-2-nitrophenyl)-N'-(5-ethylisoxazol-3-yl)urea

Conditions

Conditions	Yield
In toluene at 70 - 100℃; for 38h;	28%

: 21080-83-1
5-cyclopropylisoxazole-3-carbonyl azide

: 616-86-4
2-nitro-4-ethoxyaniline

: N-(5-cyclopropylisoxazol-3-yl)-N'-(4-ethoxy-2-nitrophenyl)urea

Conditions

Conditions	Yield
In toluene at 70 - 100℃; for 38h;	27%

: 108-31-6
maleic anhydride

: 616-86-4
2-nitro-4-ethoxyaniline

: N-(4-ethoxy-2-nitro-phenyl)-maleamic acid

: 108-30-5
succinic acid anhydride

: 616-86-4
2-nitro-4-ethoxyaniline

: N-(4-ethoxy-2-nitro-phenyl)-succinamic acid

Conditions

Conditions	Yield
With xylene

: 75-44-5
phosgene

: 616-86-4
2-nitro-4-ethoxyaniline

: 108128-49-0
4-ethoxy-1-isocyanato-2-nitrobenzene

: 75-44-5
phosgene

: 616-86-4
2-nitro-4-ethoxyaniline

: (4-ethoxy-2-nitro-phenyl)-urea

Conditions

Conditions	Yield
With ammonia; toluene; benzene at 0℃;

: 616-86-4
2-nitro-4-ethoxyaniline

: 89979-06-6
1-chloro-4-ethoxy-2-nitrobenzene

Conditions

Conditions	Yield
Diazotization.Behandeln mit CuCl;

: 616-86-4
2-nitro-4-ethoxyaniline

: 1197-37-1
4-ethoxy-benzene-1,2-diamine

Conditions

Conditions	Yield
With ethanol; nickel Hydrogenation;
With hydrogenchloride; tin(ll) chloride
With hydrazine hydrate; nickel at 60 - 70℃; for 5h;

: 616-86-4
2-nitro-4-ethoxyaniline

: 139085-95-3
1-bromo-4-ethoxy-2-nitrobenzene

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite Erhitzen des Reaktionsgemisches mit Kupfer(I)-bromid und Bromwasserstoffsaeure;

: 616-86-4
2-nitro-4-ethoxyaniline

: 3,4-dinitro-phenetole

Conditions

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite Behandlung des gebildeten Diazoniumsalzes mit NaNO2 und Kupfer-Pulver in Wasser;

: 616-86-4
2-nitro-4-ethoxyaniline

: 621-52-3
1-ethoxy-3-nitrobenzene

Benzenamine,4-ethoxy-2-nitro- Specification

The Benzenamine,4-ethoxy-2-nitro-, with CAS registry number 616-86-4, belongs to the following product category: Intermediates of Dyes and Pigments. It has the systematic name of 4-ethoxy-2-nitroaniline. This chemical is a kind of red to rust-brown crystals or crystalline powder. What's more, its EINECS is 210-497-8.

Physical properties of Benzenamine,4-ethoxy-2-nitro-: (1)ACD/LogP: 2.47; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.47; (4)ACD/LogD (pH 7.4): 2.47; (5)ACD/BCF (pH 5.5): 44.65; (6)ACD/BCF (pH 7.4): 44.65; (7)ACD/KOC (pH 5.5): 527.88; (8)ACD/KOC (pH 7.4): 527.89; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 58.29 Å²; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 48.34 cm³; (15)Molar Volume: 144 cm³; (16)Polarizability: 19.16×10^-24cm³; (17)Surface Tension: 51 dyne/cm; (18)Density: 1.264 g/cm³; (19)Flash Point: 163.2 °C; (20)Enthalpy of Vaporization: 59.04 kJ/mol; (21)Boiling Point: 346.2 °C at 760 mmHg; (22)Vapour Pressure: 5.83E-05 mmHg at 25°C.

Uses of Benzenamine,4-ethoxy-2-nitro-: it can be used to produce 5-ethoxy-2-ethylbenzimidazole. This reaction will need reagent TiO₂. The reaction time is 4 hour(s). The yield is about 96%.

When you are using this chemical, please be cautious about it as the following:
The Benzenamine,4-ethoxy-2-nitro- irritates to eyes, respiratory system and skin. And this chemical is harmful by inhalation, in contact with skin and if swallowed. When use it, wear suitable protective clothing, gloves and eye/face protection. If 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: [O-][N+](=O)c1c(ccc(OCC)c1)N
(2)InChI: InChI=1/C8H10N2O3/c1-2-13-6-3-4-7(9)8(5-6)10(11)12/h3-5H,2,9H2,1H3
(3)InChIKey: ISFYBUAVOZFROB-UHFFFAOYAU
(4)Std. InChI: InChI=1S/C8H10N2O3/c1-2-13-6-3-4-7(9)8(5-6)10(11)12/h3-5H,2,9H2,1H3
(5)Std. InChIKey: ISFYBUAVOZFROB-UHFFFAOYSA-N

Product Name

4-ETHOXY-2-NITROANILINE

Synthetic route

Benzenamine,4-ethoxy-2-nitro- Specification

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