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100-15-2 Usage

Uses

Different sources of media describe the Uses of 100-15-2 differently. You can refer to the following data:
1. N-methyl-4-nitroaniline is a stabilizer for gunpowder, a desensitizing agent for molten cast explosive TNAZ, a widely used organic intermediate, and N-methyl-4-nitroaniline can be used as a reference substance by its polarizing properties. N-methyl-4-nitroaniline is an attractive candidate for its appealing capability to retain the nitrogen oxides, good thermal stability, and facile synthesis from abundant and inexpensive starting materials.
2. N-Methyl-4-nitroaniline is a versatile reactant used in the synthesis of oxindoles using Pd-catalyzed cyclization of chloroacetanilides.

Biodegradation

N-Methyl-4-nitroaniline is used as an additive to lower the melting temperature of energetic materials in the synthesis of insensitive explosives. Although the biotransformation of N-Methyl-4-nitroaniline under anaerobic condition has been reported, its aerobic microbial degradation has not been documented yet. A soil microcosms study showed the efficient aerobic degradation of N-Methyl-4-nitroaniline by the inhabitant soil microorganisms.

Chemical Properties

brownish-yellow crystalline powder

General Description

Brownish-yellow prisms with violet reflex (from ethanol) or yellow powder.

Air & Water Reactions

N-Methyl-4-nitroaniline may be sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

N-Methyl-4-nitroaniline has a vigorous exothermic reaction with carbaryl sulfate when heated above 167° F.

Fire Hazard

Flash point data for N-Methyl-4-nitroaniline are not available; however, N-Methyl-4-nitroaniline is probably combustible.

Purification Methods

Crystallise the aniline from aqueous EtOH. [Beilstein 12 H 714.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-15-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 100-15:
(5*1)+(4*0)+(3*0)+(2*1)+(1*5)=12
12 % 10 = 2
So 100-15-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O2/c1-8-6-2-4-7(5-3-6)9(10)11/h2-5,8H,1H3

100-15-2 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A15548)  N-Methyl-4-nitroaniline, 97%   

  • 100-15-2

  • 5g

  • 351.0CNY

  • Detail
  • Alfa Aesar

  • (A15548)  N-Methyl-4-nitroaniline, 97%   

  • 100-15-2

  • 25g

  • 595.0CNY

  • Detail
  • Alfa Aesar

  • (A15548)  N-Methyl-4-nitroaniline, 97%   

  • 100-15-2

  • 100g

  • 1697.0CNY

  • Detail
  • Aldrich

  • (269638)  N-Methyl-4-nitroaniline  97%

  • 100-15-2

  • 269638-25G

  • 285.48CNY

  • Detail
  • Aldrich

  • (269638)  N-Methyl-4-nitroaniline  97%

  • 100-15-2

  • 269638-100G

  • 778.05CNY

  • Detail

100-15-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Methyl-4-nitroaniline

1.2 Other means of identification

Product number -
Other names Aniline,N-methyl-p-nitro

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-15-2 SDS

100-15-2Synthetic route

p-Nitrophenyl-N-methyl-carbamidsaeure-methylester
10252-27-4

p-Nitrophenyl-N-methyl-carbamidsaeure-methylester

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With tert-butylamine In methanol for 14h; Heating;100%
With sodium hydroxide; cetyltrimethylammonim bromide In methanol; water at 68.5℃; Rate constant;
N-Methylformamide
123-39-7

N-Methylformamide

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With potassium hydroxide100%
at 130℃; for 11h;74%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

methylamine
74-89-5

methylamine

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;96.4%
With copper(l) iodide; 6,7-dihydro-5H-quinolin-8-one oxime; potassium hydroxide In water at 25℃; for 24h; Inert atmosphere;85%
4-nitro-aniline
100-01-6

4-nitro-aniline

methyl iodide
74-88-4

methyl iodide

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With C24H52B20Cl2Rh2Se2 In toluene at 20℃; for 2h;95%
In methanol for 10h; Heating;41.1%
With methanol at 95℃;
(Z)-N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)-3,3-dimethylbut-1-en-2-yl>acetamidine
124251-71-4

(Z)-N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)-3,3-dimethylbut-1-en-2-yl>acetamidine

A

3,3-dimethyl-1-(phenylthio)butan-2-one
37471-41-3

3,3-dimethyl-1-(phenylthio)butan-2-one

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 6h; Heating;A 95%
B n/a
tert-butyl N-methyl-N-(4-nitrophenyl)carbamate
474020-88-7

tert-butyl N-methyl-N-(4-nitrophenyl)carbamate

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃;95%
With tert-butylamine In methanol for 24h; Heating;7%
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

methylamine
74-89-5

methylamine

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With copper In water at 100℃; for 12h; Ullmann reaction;93.4%
at 20℃; for 16h; Heating; Sealed tube;4.5 g
In water at 90℃; for 16h; Sealed tube;2.4 g
4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

methylamine
74-89-5

methylamine

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
In water for 16h; Pressure bomb;93%
With copper In water at 100℃; for 24h; Ullmann reaction;91.5%
With 1:1 complex of Cl- with methylamine In ethanol at 150℃; sealed tube;84%
In ethanol at 130℃; for 6h;79%
With ethanol at 160℃;
methanamine hydrochloride salt

methanamine hydrochloride salt

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 70℃; Inert atmosphere;93%
methylamine hydrochloride
593-51-1

methylamine hydrochloride

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 70℃; Inert atmosphere;93%
N-methyl-N-nosyl-p-nitroaniline
900537-31-7

N-methyl-N-nosyl-p-nitroaniline

mercaptoacetic acid
68-11-1

mercaptoacetic acid

A

2-(4-nitrophenylthio)acetic acid
3406-75-5

2-(4-nitrophenylthio)acetic acid

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃;A n/a
B 92%
methanol
67-56-1

methanol

4-nitro-aniline
100-01-6

4-nitro-aniline

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With C19H37IrN4(2+)*2I(1-); potassium carbonate at 120℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube;92%
With C12H16IrN4O2(1+)*BF4(1-); potassium hydroxide at 120℃; for 5h; Irradiation; Inert atmosphere; Sealed tube;60%
With [(N,N′-bis(diisopropylphosphino)-2,6-diaminopyridine)Mn(CO)3][Br]; potassium tert-butylate In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique;59%
N-(4-(dimethylamino)benzyl)-N-methyl-4-nitroaniline
1469886-93-8

N-(4-(dimethylamino)benzyl)-N-methyl-4-nitroaniline

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With water; trifluoroacetic acid In acetonitrile at 80℃; for 5h; Sealed tube;91%
N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-4-nitroaniline
111098-19-2

N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-4-nitroaniline

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran for 0.333333h; Heating;89%
N-Methylformamide
123-39-7

N-Methylformamide

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;89%
benzyl methyl(4-nitrophenyl)carbamate

benzyl methyl(4-nitrophenyl)carbamate

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With tert-butylamine In methanol for 24h; Heating;86%
ethyl N-methyl-N-4-nitrophenylcarbamate
80179-76-6

ethyl N-methyl-N-4-nitrophenylcarbamate

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With tert-butylamine In methanol for 56h; Heating;86%
N-methyl-4-nitro-N-(phenylthio)benzenamine
110228-59-6

N-methyl-4-nitro-N-(phenylthio)benzenamine

A

N-methyl-2-(phenylthio)-4-nitroaniline
110228-60-9

N-methyl-2-(phenylthio)-4-nitroaniline

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In acetonitrile for 0.166667h; Mechanism; Product distribution; Ambient temperature; various solvents, Lewis acids, and N-methylbenzenesulfenanilide;A 7%
B 65%
C 84%
In benzene at 85℃; for 144h;A 83%
B 15%
C 14%
With boron trifluoride diethyl etherate In benzene for 0.166667h; Ambient temperature;A 26%
B 36%
C 63%
p-nitro-N-(p-tolylthiomethyl)aniline
78520-48-6

p-nitro-N-(p-tolylthiomethyl)aniline

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,2-dimethoxyethane for 0.5h; Heating;84%
1-(p-nitrophenyl)-3-cyano-1-methyltriazene
84984-22-5

1-(p-nitrophenyl)-3-cyano-1-methyltriazene

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With sodium hydroxide In methanol for 0.5h; Heating;83%
methanol
67-56-1

methanol

A

methyl nitrite
624-91-9

methyl nitrite

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With N-methyl-N-nitroso-4-nitroaniline for 3.5h; Irradiation;A 81%
B 87 % Turnov.
N-methyl-N-nitroso-4-nitroaniline
943-41-9

N-methyl-N-nitroso-4-nitroaniline

A

methyl nitrite
624-91-9

methyl nitrite

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With methanol for 3.5h; Irradiation;A 81%
B 87 % Turnov.
N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)pent-1-en-2-yl>acetamidine
124251-66-7, 124251-73-6

N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)pent-1-en-2-yl>acetamidine

A

1-(phenylthio)pentan-2-one
38793-73-6

1-(phenylthio)pentan-2-one

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;A 80%
B n/a
N-methyl-N-(4-nitrophenyl)-N-<1-phenyl-2-(phenylthio)vinyl>acetamidine
113450-79-6, 113450-80-9, 124251-68-9, 124251-75-8

N-methyl-N-(4-nitrophenyl)-N-<1-phenyl-2-(phenylthio)vinyl>acetamidine

A

1-phenyl-2-(phenylthio)ethanone
16222-10-9

1-phenyl-2-(phenylthio)ethanone

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;A 80%
B n/a
N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)hex-1-en-2-yl>acetamidine
113450-77-4, 113450-78-5, 124251-67-8, 124251-74-7

N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)hex-1-en-2-yl>acetamidine

A

1-(Phenylthio)hexan-2-one
66716-59-4

1-(Phenylthio)hexan-2-one

B

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;A 80%
B n/a
N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

A

N-methyl-N-nitrosoaniline
614-00-6

N-methyl-N-nitrosoaniline

B

nitrobenzene
98-95-3

nitrobenzene

C

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

D

N-methyl-N-nitroso-4-nitroaniline
943-41-9

N-methyl-N-nitroso-4-nitroaniline

Conditions
ConditionsYield
With n-Butyl nitrite; ammonium chloride; water for 2h; Heating;A 2%
B 1%
C 4%
D 80%
4-nitro-aniline
100-01-6

4-nitro-aniline

2-(2-Methoxyethoxy)ethyl methyl carbonate
141814-27-9

2-(2-Methoxyethoxy)ethyl methyl carbonate

A

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

B

N,N-Dimethyl-4-nitroaniline
100-23-2

N,N-Dimethyl-4-nitroaniline

Conditions
ConditionsYield
With NaY at 160℃; for 4.16667h;A 80%
B n/a
BF4(1-)*C13H15N2O3(1+)

BF4(1-)*C13H15N2O3(1+)

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With methanol; sodium methylate80%
N-(4-nitrophenyl)-1H-imidazole-1-carboxamide
134773-18-5

N-(4-nitrophenyl)-1H-imidazole-1-carboxamide

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 20 - 66℃; for 6h;80%
furan
110-00-9

furan

N-methyl-4-nitro-N-(phenylthio)benzenamine
110228-59-6

N-methyl-4-nitro-N-(phenylthio)benzenamine

A

2-phenylthiofuran
16003-14-8

2-phenylthiofuran

B

N-methyl-2-(phenylthio)-4-nitroaniline
110228-60-9

N-methyl-2-(phenylthio)-4-nitroaniline

C

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

D

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
at 85℃; for 144h;A 40%
B 4%
C 79%
D 25%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methyl-benzene-1,4-diamine
623-09-6

N-methyl-benzene-1,4-diamine

Conditions
ConditionsYield
With hydrogen In ethyl acetate under 1551.44 Torr;100%
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen; sodium triethylborohydride In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique;100%
Stage #1: N-methyl(p-nitroaniline) With palladium 10% on activated carbon In tetrahydrofuran at 60℃; for 1.5h;
Stage #2: With ammonium formate In tetrahydrofuran for 1.5h;
94%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

(2-bromo-4-nitro-phenyl)-methyl-amine
6911-88-2

(2-bromo-4-nitro-phenyl)-methyl-amine

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile for 0.5h; Cooling with ice;100%
Stage #1: N-methyl(p-nitroaniline) With bromine; acetic acid In chloroform at 5 - 10℃; for 1h;
Stage #2: With sodium hydrogencarbonate In chloroform; water
99%
With bromine; acetic acid In chloroform at 5 - 10℃; for 1h;99%
With bromine; acetic acid
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

tert-butyl N-methyl-N-(4-nitrophenyl)carbamate
474020-88-7

tert-butyl N-methyl-N-(4-nitrophenyl)carbamate

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; for 2h; Reflux; Inert atmosphere;100%
With dmap In tetrahydrofuran at 0 - 20℃; Inert atmosphere;90%
Stage #1: N-methyl(p-nitroaniline) With dmap In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate With triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
60%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

(2-bromo-4-nitro-phenyl)-methyl-amine (2-bromo-4-nitro-phenyl)-methyl-amine

(2-bromo-4-nitro-phenyl)-methyl-amine (2-bromo-4-nitro-phenyl)-methyl-amine

Conditions
ConditionsYield
With bromine In chloroform; acetic acid99%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

ethyl 2-(N-methyl-N-(4-nitrophenyl)amino)acetate

ethyl 2-(N-methyl-N-(4-nitrophenyl)amino)acetate

Conditions
ConditionsYield
With porous-polymer-supported ruthenium(II)-phenyloxazoline complex catalyst In dichloromethane at 20℃; for 0.25h; Inert atmosphere;99%
With [2-(4-hydroxymethyl)phenyl-4,4-(dimethyloxazole)Ru(CH3CN)4]PF6 In diethyl ether; water at 20℃; for 3h;75%
methyl isocyanate
624-83-9

methyl isocyanate

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

1,3-Dimethyl-1-(4-nitro-phenyl)-urea
97006-33-2

1,3-Dimethyl-1-(4-nitro-phenyl)-urea

Conditions
ConditionsYield
In toluene at 80℃; for 72h;98%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

3-(propa-1,2-dienyl)oxazolidin-2-one
250728-91-7

3-(propa-1,2-dienyl)oxazolidin-2-one

(E)-3-(3-(methyl(4-nitrophenyl)amino)prop-1-en-1-yl)oxazolidin-2-one
1235581-17-5

(E)-3-(3-(methyl(4-nitrophenyl)amino)prop-1-en-1-yl)oxazolidin-2-one

Conditions
ConditionsYield
With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; stereoselective reaction;98%
With ethyldiphenylphosphine-functionalized MCM-41-anchored AuNTf2 In dichloromethane at 20℃; for 4h;96%
2-bromo-N-(tert-butyl)cyclopropanecarboxamide
1158733-15-3

2-bromo-N-(tert-butyl)cyclopropanecarboxamide

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-(tert-Butyl)-2-(methyl(4-nitrophenyl)amino)-cyclopropanecarboxamide

N-(tert-Butyl)-2-(methyl(4-nitrophenyl)amino)-cyclopropanecarboxamide

Conditions
ConditionsYield
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran at 55℃; for 12h; Inert atmosphere; diastereoselective reaction;98%
1,4-dithiino<2,3-c;6,5-c'>diisothiazole-3,7-dicarbonyl chloride
63419-83-0

1,4-dithiino<2,3-c;6,5-c'>diisothiazole-3,7-dicarbonyl chloride

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N,N'-Bis(4-nitrophenyl)-N,N'-dimethyl-1,4-dithiino<2,3-c;6,5-c'>diisothiazol-3,7-dicarboxamid
63419-92-1

N,N'-Bis(4-nitrophenyl)-N,N'-dimethyl-1,4-dithiino<2,3-c;6,5-c'>diisothiazol-3,7-dicarboxamid

Conditions
ConditionsYield
In 1,2-dichloro-ethane for 2h; Heating;96%
(acetylamino)acetaldehyde dimethyl acetal
62005-48-5

(acetylamino)acetaldehyde dimethyl acetal

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-(2-(methyl(4-nitrophenyl)amino)ethyl)acetamide
1262142-15-3

N-(2-(methyl(4-nitrophenyl)amino)ethyl)acetamide

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;96%
naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methyl-N-(4-nitrophenyl)naphthalen-2-amine

N-methyl-N-(4-nitrophenyl)naphthalen-2-amine

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane at 0 - 5℃; for 4h; Sonication; Green chemistry;96%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

N-methyl-4-nitro-N-(trifluoromethyl)aniline
143490-25-9

N-methyl-4-nitro-N-(trifluoromethyl)aniline

Conditions
ConditionsYield
Stage #1: N-methyl(p-nitroaniline); tetramethylammonium trifluoromethanethiolate In dichloromethane at 20℃;
Stage #2: With silver fluoride In dichloromethane at 20℃; for 4h; Sonication;
96%
allyl alcohol
107-18-6

allyl alcohol

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-allyl-N-methyl-4-nitrobenzenamine

N-allyl-N-methyl-4-nitrobenzenamine

Conditions
ConditionsYield
With titanium(IV) isopropylate; palladium diacetate; triphenylphosphine In toluene at 115℃; for 5h; Inert atmosphere;96%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide
2653-16-9

2-chloro-N-methyl-N-(4-nitrophenyl)acetamide

Conditions
ConditionsYield
In toluene at 100℃; for 2h;93%
In ethyl acetate at 70℃; for 1h;90%
In ethyl acetate at 70℃; for 1h;90%
Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methoxyacetyl-N-methyl-4-amino-nitrobenzene
674772-03-3

N-methoxyacetyl-N-methyl-4-amino-nitrobenzene

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 20h;93%
4-trifluoromethylphenylboronic acid
128796-39-4

4-trifluoromethylphenylboronic acid

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methyl-4-nitro-N-(4-(trifluoromethyl)phenyl)aniline

N-methyl-4-nitro-N-(4-(trifluoromethyl)phenyl)aniline

Conditions
ConditionsYield
With copper diacetate; triethylamine In dichloromethane at 0 - 5℃; for 4h; Sonication; Green chemistry;93%
N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methyl-N-nitroso-4-nitroaniline
943-41-9

N-methyl-N-nitroso-4-nitroaniline

Conditions
ConditionsYield
With hydrogenchloride; 1-butyl-3-methylimidazolium nitrite In water at 5 - 25℃; for 0.533333h;92%
With oxygen; nitrogen(II) oxide In 1,2-dichloro-ethane for 24h; Ambient temperature;90%
Stage #1: N-methyl(p-nitroaniline) With hydrogenchloride In water at 0℃;
Stage #2: With 1-(4-(nitrosooxy)butyl)-3-methylimidazolium chloride at 0 - 25℃; for 1.5h;
90%
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

N-methyl(p-nitroaniline)
100-15-2

N-methyl(p-nitroaniline)

N-methyl-N-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine

N-methyl-N-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidine-4-amine

Conditions
ConditionsYield
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine; N-methyl(p-nitroaniline) With hydrogenchloride In 1,4-dioxane at 130℃;
Stage #2: With triethylamine In methanol
91.5%

100-15-2Relevant articles and documents

Some properties of 1-(nitrophenyl)-aminobenzimidazoles

Dyablo,Pozharskii,Shkurupii

, p. 37 - 39 (2000)

The chemical properties of previously synthesized 1-[2(4)-nitrophenyl]aminobenzimidazoles, in particular, alkylation at the NH group, thiolation, and reduction were studied.

Methanolysis of thioamide promoted by a simple palladacycle is accelerated by 108 over the methoxide-catalyzed reaction

Liu, C. Tony,Maxwell, Christopher I.,Pipe, Stephanie G.,Neverov, Alexei A.,Mosey, Nicholas J.,Brown, R. Stan

, p. 20068 - 20071 (2011)

Palladacycle 1 catalyzes the methanolytic cleavage of N-methyl-N-(4- nitrophenyl)thiobenzamide (4) via a mechanism involving formation of a Pd-bound tetrahedral intermediate (TI). The rate constant for decomposition of the complex formed between 1, methox

Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2

Suárez-Castillo, Oscar R.,Montiel-Ortega, Luis Alberto,Meléndez-Rodríguez, Myriam,Sánchez-Zavala, Maricruz

, p. 17 - 20 (2007)

An efficient, simple protocol for the selective cleavage of a variety of N-alkoxycarbonyl protecting groups by t-BuNH2/MeOH is described. The scope of the procedure was explored for a series of indole, aniline and pyrrolidine carbamate derivatives containing other potentially reactive functional groups affording a clean cleavage of the carbamate group.

Synthesis of some heterocycle containing urea derivatives and their anti-viral activity

Verma, Majusha,Singh, Krishna N.,Clercq, Erik D.

, p. 11 - 22 (2006)

Some new isoindol heterocyclic ureas (6a-6i) have been synthesized using N-aminophthalimide (2) and ethyl N-monosubstituted/ethyl N,N-disubstituted carbamate (5a-5i). All the newly synthesized final compounds have been evaluated for their anti-viral activities against a variety of viruses. The compound (6f) with the methoxy substituent showed reasonably better activity as compared to the standard drugs against all the viruses (cf. Tables 1, 2 and 3). Further, all the products (6a-6i) were found to be active against Vesicular stomatitis virus, Coxsackie virus B4 and Respiratory syncytical virus (cf. Table 2) and the compounds (6h) and (6i) displayed better antiviral activity in comparison to Brivudin and (S)-DHPA (cf. Table 3).

Methylation of aniline and its derivatives with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY

Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.,Ardieva,Khazipova,Kutepov

, p. 1565 - 1570 (2016)

Aniline and its derivatives undergo methylation when treated with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY leading to the formation of N-methyl- and N,N-dimethylanilines.

Synergistic effect of cyclodextrin-based binuclear complexes in the hydrolysis of amide

Yan, Jia-Ming,Atsumi, Masato,Yuan, De-Qi,Fujita, Kahee

, p. 1825 - 1828 (2000)

Novel cyclodextrin-based binuclear metal complexes have been prepared and proved to be far more efficient than their mononuclear complexes in promoting amide hydrolysis. (C) 2000 Elsevier Science Ltd.

Efficient and versatile catalytic systems for the n-methylation of primary amines with methanol catalyzed by n-heterocyclic carbene complexes of iridium

Toyooka, Genki,Tuji, Akiko,Fujita, Ken-Ichi

, p. 4617 - 4626 (2018)

Efficient and versatile catalytic systems were developed for the N-methylation of both aliphatic and aromatic primary amines using methanol as the methylating agent. Iridium complexes bearing an Nheterocyclic carbene (NHC) ligand exhibited high catalytic performance for this type of transformation. For aliphatic amines, selective N,N-dimethylation was achieved at low temperatures (50-90 °C). For aromatic amines, selective N-monomethylation and selective N,N-dimethylation were accomplished by simply changing the reaction conditions (presence or absence of a base with an appropriate catalyst). These findings can be used to develop methods for synthesizing useful amine compounds having N-methyl or N,N-dimethyl moieties.

Facile method for the monomethylation of anilines

Ha, Hyun-Joon,Ahn, Young-Gil

, p. 1543 - 1546 (1997)

The monomethylation of anilines was achieved in high yield from the reaction of 1,3,5-triphenylhexahydro-1,3,5-triazines with BH3·S(CH3)2 followed by hydrolysis.

-

White et al.

, p. 3166 (1976)

-

Construction of interconnected acidity functions based on ortho substituted anilines and N-methylanilines as indicators

Pytela, Oldrich,Kulhanek, Jiri,Jiraskova, Eva,Nevecna, Tatjana

, p. 1638 - 1658 (2001)

The log I values of 15 mainly ortho substituted derivatives of aniline and N-methylaniline have been measured spectrophotometrically in sulfuric, perchloric, and methanesulfonic acids. A new algorithm has been suggested for construction of acidity functions enabling simultaneous and independent construction of acidity functions in various media under the condition of equal values of pKa of the same indicators in the given media. The so-called interconnected acidity functions have been constructed with using this algorithm and the log I values measured in the above media, and the pKa values have been calculated. The resulting acidity functions and pKa values agree well with the corresponding literature data.

Tandem Transformation of Nitro Compounds into N-Methylated Amines: Greener Strategy for the Utilization of Methanol as a Methylating Agent

Paul, Bhaskar,Shee, Sujan,Chakrabarti, Kaushik,Kundu, Sabuj

, p. 2370 - 2374 (2017)

A simple air- and moisture-stable, highly efficient ruthenium NNN pincer complex is reported for the first time to catalyze the tandem transformation of various aromatic and aliphatic nitro compounds into the corresponding N-methylated amines in up to 98 % yield by using methanol as a green methylating agent. Gram-scale reactions of challenging nitro substrates demonstrated the practical application aspects of this catalytic system. Importantly, the N-methylamine moiety could be smoothly introduced to various complex molecular structures without using any expensive palladium/phosphine/amine-based cross-coupling reactions.

Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water

Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming

, p. 714 - 718 (2015)

The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.

Reaction of primary aromatic amines with alkyl carbonates over NaY faujasite: A convenient and selective access to mono-N-alkyl anilines

Selva,Tundo,Perosa

, p. 677 - 680 (2001)

At atmospheric pressure and at 130-160°C, primary aromatic amines (p-XC6H4NH2, X = H, Cl, NO2) are mono-N-alkylated in a single step, with symmetrical and asymmetrical dialkyl carbonates [ROCOOR′, R = Me, R′ = MeO(CH2)2O(CH2)2; R = R′ = Et; R = R′ = benzyl; R = R′ = allyl; R = Et, R′ = MeO(CH2)2O(CH2)2], in the presence of a commercially available NaY faujasite. No solvents are required. Mono-N-alkyl anilines are obtained with a very high selectivity (90-97%), in good to excellent yields (68-94%), on a preparative scale. In the presence of triglyme as a solvent, the mono-N-alkyl selectivity is independent of concentration and polarity factors. The reaction probably takes place within the polar zeolite cavities, and through the combined effect of the dual acid-base properties of the catalyst.

N-Alkylation of Aniline Derivatives by Use of Potassium Cation-exchanged Y-Type Zeolite

Onaka, Makoto,Umezono, Akihiro,Kawai, Motomitsu,Izumi, Yusuke

, p. 1202 - 1203 (1985)

Zeolite K-Y is effective as a promoter in the N-alkylation of aniline derivatives in comparison with γ-alumina.

-

Stoermer,Hoffmann

, p. 2529 (1898)

-

A convenient one pot procedure for N-methylation of aromatic amines using trimethyl orthoformate

Padmanabhan, Seetharamaiyer,Reddy, N. Laxma,Durant, Graham J.

, p. 691 - 699 (1997)

Aromatic amines react with trimethyl orthoformate in the presence of concentrated sulfuric acid followed by acid hydrolysis to afford mono methylated amines in moderate to good yields.

To what extent can a conjugation between two pairs of peri-nitro and peri-amino groups be realized through the naphthalene core?

Ozeryanskii, Valery A.,Filatova, Ekaterina A.,Pozharskii, Alexander F.,Shevchuk, Dmitrii A.,Sorokin, Vladimir I.

, p. 492 - 502 (2013)

Through-conjugation for a wide range of 1,8-diamino-4,5-dinitronaphthalenes (N-acylated, N-alkylated, N,N′-bridged, N-heterocyclic, and N-deprotonated compounds) was for the first time quantified in solution by means of ultraviolet-visible and proton nucl

INTERVENTION OF N,N-DIMETHYLANILINIUM CATION RADICAL IN THE POLONONOVSKI TYPE REACTION OF N,N-DIMETHYLANILINE N-OXIDE CATALYZED BY MESO-TETRAPHENYLPORPHINATOIRON/IMIDAZOLE

Fujimori, Ken,Takata, Toshikazu,Fujiwara, Seiichi,Kikuchi, Osamu,Oae, Shigeru

, p. 1617 - 1620 (1986)

Meso-tetraphenylporphinatoiron(III)/imidazole catalyzes the Polonovski type reaction of substituted N,N-dimethylaniline N-oxides to give mixtures of N-demethylated and N-deoxygenated products.Effect of substituent on the turnover number and the ratio of the demethylation to the deoxygenation, and other observations suggest that the Polonovski type N-demethylation reaction takes place via the rate determining N,N-dimethylanilinium cation radical formation.

Methanol dehydrogenation by iridium N-heterocyclic carbene complexes

Campos, Jesús,Sharninghausen, Liam S.,Manas, Michael G.,Crabtree, Robert H.

, p. 5079 - 5084 (2015)

A series of homogeneous iridium bis(N-heterocyclic carbene) catalysts are active for three transformations involving dehydrogenative methanol activation: acceptorless dehydrogenation, transfer hydrogenation, and amine monoalkylation. The acceptorless dehydrogenation reaction requires base, yielding formate and carbonate, as well as 2-3 equivalents of H2. Of the few homogeneous systems known for this reaction, our catalysts tolerate air and employ simple ligands. Transfer hydrogenation of ketones and imines from methanol is also possible. Finally, N-monomethylation of anilines occurs through a borrowing hydrogen reaction. Notably, this reaction is highly selective for the monomethylated product.

-

Borch,R.F.,Hassid,A.I.

, p. 1673 - 1674 (1972)

-

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei

supporting information, p. 7534 - 7538 (2021/10/12)

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

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