Product Name

  • Name

    (4-Amino-2-nitrophenyl)carbamic acid ethyl ester

  • EINECS
  • CAS No. 73895-87-1
  • Article Data5
  • CAS DataBase
  • Density 1.411 g/cm3
  • Solubility
  • Melting Point
  • Formula C9H11N3O4
  • Boiling Point 359.9 °C at 760 mmHg
  • Molecular Weight 225.204
  • Flash Point 171.5 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 73895-87-1 ((4-Amino-2-nitrophenyl)carbamic acid ethyl ester)
  • Hazard Symbols
  • Synonyms Ethyl (4-amino-2-nitrophenyl) carbamate;
  • PSA 113.66000
  • LogP 2.86340

Synthetic route

2-ethoxycarbonylamino-5-phthalimidonitrobenzene
150812-24-1

2-ethoxycarbonylamino-5-phthalimidonitrobenzene

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
With methylamine In water; isopropyl alcohol at 60 - 65℃; for 2h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;97.2%
With hydrazine In 1,2-dimethoxyethane for 1.66667h; Heating / reflux;90%
With hydrazine hydrate In 1,2-dimethoxyethane
N-(4-aminophenyl)carbamic acid ethyl ester
57399-97-0

N-(4-aminophenyl)carbamic acid ethyl ester

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.5h; Inert atmosphere;60%
Stage #1: N-(4-aminophenyl)carbamic acid ethyl ester With sulfuric acid In water at -5℃;
Stage #2: With nitric acid In water at 0℃; for 0.5h; Inert atmosphere;		60%
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 2.5 h / 20 - 95 °C / Inert atmosphere
2: nitric acid / acetic acid / 20 - 105 °C / Inert atmosphere
3: methylamine / isopropyl alcohol; water / 2 h / 60 - 65 °C
View Scheme
1-ethoxycarbonylamino-4-phthalimidobenzene
721943-05-1

1-ethoxycarbonylamino-4-phthalimidobenzene

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / acetic acid / 20 - 105 °C / Inert atmosphere
2: methylamine / isopropyl alcohol; water / 2 h / 60 - 65 °C
View Scheme
ethyl 4-nitrophenylcarbamate
2621-73-0

ethyl 4-nitrophenylcarbamate

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; 5%-palladium/activated carbon / tetrahydrofuran; water / 24 h / 50 °C / Inert atmosphere
2: sulfuric acid; nitric acid / water / 0.5 h / -5 - 0 °C / Inert atmosphere
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene
1314406-56-8

2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 4h; Reflux;100%
In ethanol at 20 - 65℃; Solvent; Temperature;97.9%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

C16H16FN3O4

C16H16FN3O4

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 3-Fluorobenzaldehyde With toluene-4-sulfonic acid In toluene for 4h; Reflux;
Stage #2: With methanol; sodium tetrahydroborate In ethyl acetate at 10℃; for 4h;		88.6%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

C16H16FN3O4

C16H16FN3O4

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 2-Fluorobenzaldehyde With toluene-4-sulfonic acid In toluene for 4h; Reflux;
Stage #2: With methanol; sodium tetrahydroborate In ethyl acetate at 10℃; for 4h;		87%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene
150812-23-0

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene

Conditions
ConditionsYield
With sodium tetrahydroborate In water; isopropyl alcohol at 20℃; Solvent; Temperature; Time;81.7%
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 35℃;
Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran at 35℃; for 1h;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-(4-chloro-benzenesulfonyl)-3-methyl-thiophene-2-carbaldehyde
721943-14-2

4-(4-chloro-benzenesulfonyl)-3-methyl-thiophene-2-carbaldehyde

C21H18ClN3O6S2
721943-40-4

C21H18ClN3O6S2

Conditions
ConditionsYield
In ethanol for 20h; Heating / reflux;61%
5-Chloro-2-thiophenecarboxaldehyde
7283-96-7

5-Chloro-2-thiophenecarboxaldehyde

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

(2-amino-4-((5-chloro-thiophen-2-ylmethyl)-amino)-phenyl)-carbamic acid ethyl ester

(2-amino-4-((5-chloro-thiophen-2-ylmethyl)-amino)-phenyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-Chloro-2-thiophenecarboxaldehyde; 5-amino-2-ethoxycarbonylaminonitrobenzene With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 40℃; for 3.5h; Ultrasonic bath;
Stage #2: With hydrogenchloride; iron In ethanol; water for 0.166667h;		56%
5-methylthiophene-2-carboxaldehyde
13679-70-4

5-methylthiophene-2-carboxaldehyde

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

C15H15N3O4S

C15H15N3O4S

Conditions
ConditionsYield
Amberlite IRC-84 In o-xylene for 5h; Heating / reflux;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

5-fluorobenzofuran-3-carbaldehyde
721943-19-7

5-fluorobenzofuran-3-carbaldehyde

C18H14FN3O5

C18H14FN3O5

Conditions
ConditionsYield
Amberlite IRC-84 In o-xylene for 5h; Heating / reflux;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene
150812-23-0

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
2: sodium tetrahydroborate; methanol / ethyl acetate / 4 h / 10 °C
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Retigabine
150812-12-7

Retigabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / isopropyl alcohol; water / 20 °C
2: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 20 - 65 °C
2: hydrogen; palladium 10% on activated carbon; triethylamine / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 3 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
3: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 35 °C
1.2: 1 h / 35 °C
2.1: hydrogenchloride; iron / water; ethanol / 1 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
2: sodium tetrahydroborate; methanol / ethyl acetate / 4 h / 10 °C
3: hydrogen / ethyl acetate / 15 h / 55 - 60 °C / 8250.83 Torr
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

retigabine dihydrochloride

retigabine dihydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / isopropyl alcohol; water / 20 °C
2: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
3: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: ethanol / 20 - 65 °C
2: hydrogen; palladium 10% on activated carbon; triethylamine / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
3: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
3: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
4: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Retigabine
150812-12-7

Retigabine

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 4-fluorobenzaldehyde With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 25 - 35℃;
Stage #2: With hydrogenchloride; iron In ethanol; water at 25℃; for 1h;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

C16H18FN3O2

C16H18FN3O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
1.2: 4 h / 10 °C
2.1: hydrogen / ethyl acetate / 15 h / 55 - 60 °C / 8250.83 Torr
View Scheme

(4-Amino-2-nitrophenyl)carbamic acid ethyl ester Specification

The (4-Amino-2-nitrophenyl)carbamic acid ethyl ester has CAS registry number 73895-87-1. This chemical's molecular formula is C9H11N3O4 and molecular weight is 225.20134. What's more, its systematic name is Ethyl (4-amino-2-nitrophenyl)carbamate.

Physical properties about (4-Amino-2-nitrophenyl)carbamic acid ethyl ester are: (1)ACD/LogP: 1.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.62; (4)ACD/LogD (pH 7.4): 1.62; (5)ACD/BCF (pH 5.5): 10.02; (6)ACD/BCF (pH 7.4): 10.08; (7)ACD/KOC (pH 5.5): 180.83; (8)ACD/KOC (pH 7.4): 181.92; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 110.17 Å2; (13)Index of Refraction: 1.643; (14)Molar Refractivity: 57.68 cm3; (15)Molar Volume: 159.5 cm3; (16)Polarizability: 22.86×10-24 cm3; (17)Surface Tension: 64.3 dyne/cm; (18)Density: 1.411 g/cm3; (19)Flash Point: 171.5 °C; (20)Enthalpy of Vaporization: 60.56 kJ/mol; (21)Boiling Point: 359.9 °C at 760 mmHg; (22)Vapour Pressure: 2.3E-05 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(Nc1ccc(N)cc1N(=O)=O)OCC
(2) InChI: InChI=1/C9H11N3O4/c1-2-16-9(13)11-7-4-3-6(10)5-8(7)12(14)15/h3-5H,2,10H2,1H3,(H,11,13)
(3) InChIKey: HDEBGAGNWSBAOY-UHFFFAOYAC

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