N-Methyl-4-nitroaniline supplier

Name
N-Methyl-4-nitroaniline
EINECS 202-823-2
CAS No. 100-15-2
Article Data153
CAS DataBase
Density 1.26 g/cm³
Solubility <0.1 g/100 mL at 19 °C in water
Melting Point 149-151 °C(lit.)
Formula C₇H₈N₂O₂
Boiling Point 290.6 °C at 760 mmHg
Molecular Weight 152.153
Flash Point 129.5 °C
Transport Information 2811
Appearance Brownish-yellow crystalline powder
Safety 28-36/37/39-45-26
Risk Codes 23/24/25-33-36/37/38
Molecular Structure
Hazard Symbols T,Xi
Synonyms Aniline,N-methyl-p-nitro- (6CI,7CI,8CI);4-(Methylamino)nitrobenzene;4-Nitro-N-methylaniline;Methyl(4-nitrophenyl)amine;N-Methyl-4-nitrobenzenamine;N-Methyl-p-nitraniline;N-Methyl-p-nitroaniline;N-Monomethyl-p-nitroaniline;NSC 5390;p-(Methylamino)nitrobenzene;p-Nitro-N-methylaniline;
PSA 57.85000
LogP 2.23270

Synthetic route

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

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

Conditions

Conditions	Yield
With tert-butylamine In methanol for 14h; Heating;	100%
With sodium hydroxide; cetyltrimethylammonim bromide In methanol; water at 68.5℃; Rate constant;

: 123-39-7
N-Methylformamide

: 100-00-5
4-chlorobenzonitrile

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

Conditions

Conditions	Yield
With potassium hydroxide	100%
at 130℃; for 11h;	74%

: 636-98-6
p-nitrobenzene iodide

: 74-89-5
methylamine

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

Conditions

Conditions	Yield
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%

: 100-01-6
4-nitro-aniline

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With C24H52B20Cl2Rh2Se2 In toluene at 20℃; for 2h;	95%
In methanol for 10h; Heating;	41.1%
With methanol at 95℃;

: 124251-71-4
(Z)-N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)-3,3-dimethylbut-1-en-2-yl>acetamidine

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

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 6h; Heating;	A 95% B n/a

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

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

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 25℃;	95%
With tert-butylamine In methanol for 24h; Heating;	7%

: 586-78-7
para-nitrophenyl bromide

: 74-89-5
methylamine

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

Conditions

Conditions	Yield
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

: 100-00-5
4-chlorobenzonitrile

: 74-89-5
methylamine

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

Conditions

Conditions	Yield
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

: 350-46-9
4-Fluoronitrobenzene

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 70℃; Inert atmosphere;	93%

: 593-51-1
methylamine hydrochloride

: 350-46-9
4-Fluoronitrobenzene

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

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 70℃; Inert atmosphere;	93%

: 900537-31-7
N-methyl-N-nosyl-p-nitroaniline

: 68-11-1
mercaptoacetic acid

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

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

Conditions

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

...Expand

: 67-56-1
methanol

: 100-01-6
4-nitro-aniline

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

Conditions

Conditions	Yield
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%

: 1469886-93-8
N-(4-(dimethylamino)benzyl)-N-methyl-4-nitroaniline

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

Conditions

Conditions	Yield
With water; trifluoroacetic acid In acetonitrile at 80℃; for 5h; Sealed tube;	91%

: 111098-19-2
N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-4-nitroaniline

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

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran for 0.333333h; Heating;	89%

: 123-39-7
N-Methylformamide

: 636-98-6
p-nitrobenzene iodide

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

Conditions

Conditions	Yield
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;	89%

: benzyl methyl(4-nitrophenyl)carbamate

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

Conditions

Conditions	Yield
With tert-butylamine In methanol for 24h; Heating;	86%

: 80179-76-6
ethyl N-methyl-N-4-nitrophenylcarbamate

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

Conditions

Conditions	Yield
With tert-butylamine In methanol for 56h; Heating;	86%

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

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

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

C: 882-33-7
diphenyldisulfane

Conditions

Conditions	Yield
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%

...Expand

: 78520-48-6
p-nitro-N-(p-tolylthiomethyl)aniline

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

Conditions

Conditions	Yield
With sodium tetrahydroborate In 1,2-dimethoxyethane for 0.5h; Heating;	84%

: 84984-22-5
1-(p-nitrophenyl)-3-cyano-1-methyltriazene

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

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 0.5h; Heating;	83%

: 67-56-1
methanol

A: 624-91-9
methyl nitrite

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

Conditions

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

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

A: 624-91-9
methyl nitrite

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

Conditions

Conditions	Yield
With methanol for 3.5h; Irradiation;	A 81% B 87 % Turnov.

: 124251-66-7, 124251-73-6
N-methyl-N-(4-nitrophenyl)-N'-<1-(phenylthio)pent-1-en-2-yl>acetamidine

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

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;	A 80% B n/a

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

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;	A 80% B n/a

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

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

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 0.5h; Heating; Yields of byproduct given;	A 80% B n/a

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

A: 614-00-6
N-methyl-N-nitrosoaniline

B: 98-95-3
nitrobenzene

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

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

Conditions

Conditions	Yield
With n-Butyl nitrite; ammonium chloride; water for 2h; Heating;	A 2% B 1% C 4% D 80%

...Expand

: 100-01-6
4-nitro-aniline

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

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

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

Conditions

Conditions	Yield
With NaY at 160℃; for 4.16667h;	A 80% B n/a

...Expand

: BF4(1-)*C13H15N2O3(1+)

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

Conditions

Conditions	Yield
With methanol; sodium methylate	80%

: 134773-18-5
N-(4-nitrophenyl)-1H-imidazole-1-carboxamide

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

Conditions

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 20 - 66℃; for 6h;	80%

: 110-00-9
furan

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

A: 16003-14-8
2-phenylthiofuran

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

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

D: 882-33-7
diphenyldisulfane

Conditions

Conditions	Yield
at 85℃; for 144h;	A 40% B 4% C 79% D 25%

...Expand

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
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

: 24424-99-5
di-tert-butyl dicarbonate

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

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

Conditions

Conditions	Yield
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%

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

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

Conditions

Conditions	Yield
With bromine In chloroform; acetic acid	99%

: 623-73-4
diazoacetic acid ethyl ester

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

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

Conditions

Conditions	Yield
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%

: 624-83-9
methyl isocyanate

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

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

Conditions

Conditions	Yield
In toluene at 80℃; for 72h;	98%

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

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

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

Conditions

Conditions	Yield
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%

: 1158733-15-3
2-bromo-N-(tert-butyl)cyclopropanecarboxamide

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

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

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium hydroxide In tetrahydrofuran at 55℃; for 12h; Inert atmosphere; diastereoselective reaction;	98%

: 63419-83-0
1,4-dithiino<2,3-c;6,5-c'>diisothiazole-3,7-dicarbonyl chloride

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

: 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

Conditions	Yield
In 1,2-dichloro-ethane for 2h; Heating;	96%

: 62005-48-5
(acetylamino)acetaldehyde dimethyl acetal

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

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

Conditions

Conditions	Yield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	96%

: 32316-92-0
naphthalene-2-boronic acid

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

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 0 - 5℃; for 4h; Sonication; Green chemistry;	96%

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

: tetramethylammonium trifluoromethanethiolate

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

Conditions

Conditions	Yield
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%

: 107-18-6
allyl alcohol

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

: N-allyl-N-methyl-4-nitrobenzenamine

Conditions

Conditions	Yield
With titanium(IV) isopropylate; palladium diacetate; triphenylphosphine In toluene at 115℃; for 5h; Inert atmosphere;	96%

: 79-04-9
chloroacetyl chloride

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

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

Conditions

Conditions	Yield
In toluene at 100℃; for 2h;	93%
In ethyl acetate at 70℃; for 1h;	90%
In ethyl acetate at 70℃; for 1h;	90%

: 38870-89-2
Methoxyacetyl chloride

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

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

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran for 20h;	93%

: 128796-39-4
4-trifluoromethylphenylboronic acid

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

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

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane at 0 - 5℃; for 4h; Sonication; Green chemistry;	93%

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

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

Conditions

Conditions	Yield
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%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

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

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

Conditions

Conditions	Yield
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%

N-Methyl-4-nitroaniline Specification

The N-Methyl-4-nitroaniline with CAS registry number of 100-15-2 is also known as p-(Methylamino)nitrobenzene. The IUPAC name and product name are the same. It belongs to product categories of Anilines, Aromatic Amines and Nitro Compounds; C7Photonic and Optical Materials; Amines; Nitrogen Compounds; NLO Chromophores and Intermediates; Non-Linear Optical (NLO) Materials. Its EINECS registry number is 202-823-2. In addition, the formula is C₇H₈N₂O₂ and the molecular weight is 152.15. This chemical is a brownish-yellow crystalline powder which is soluble in acetone, benzene, slightly soluble in ethanol and insoluble in water. Besides, it is used in organic synthesis and also used as dye intermediates.

Physical properties about N-Methyl-4-nitroaniline are: (1)ACD/LogP: 2.04; (2)ACD/LogD (pH 5.5): 2.04; (3)ACD/LogD (pH 7.4): 2.04; (4)ACD/BCF (pH 5.5): 20.91; (5)ACD/BCF (pH 7.4): 20.91; (6)ACD/KOC (pH 5.5): 306.73; (7)ACD/KOC (pH 7.4): 306.73; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.619; (12)Molar Refractivity: 42.4 cm³; (13)Molar Volume: 120.7 cm³; (14)Surface Tension: 50.3 dyne/cm; (15)Density: 1.26 g/cm³; (16)Flash Point: 129.5 °C; (17)Enthalpy of Vaporization: 53 kJ/mol; (18)Boiling Point: 290.6 °C at 760 mmHg; (19)Vapour Pressure: 0.00205 mmHg at 25 °C.

Preparation of N-Methyl-4-nitroaniline: it is prepared by reaction of acetanilide of nitrate, iodomethane and ethanol. Firstly, acetone, nitro acetanilide and potassium hydroxide are mixed and refluxed. Meanwhile, dropping methyl iodide acetone solution and refluxing for another 4 hours. After reactant is placed overnight, crystal precipitated is washed with ethanol to get N-methyl-nitro acetanilide. Secondly, the reactant is mixed with ethanol, hydrochloric acid, and refluxed for 8 hours. Crude product is generated by washed and drying. At last, product is obtained by dissolution, filtration and precipitation of crystals.

Uses of N-Methyl-4-nitroaniline: it is used to produce N-methyl-4-nitro-N-nitroso-aniline. The reaction occurs with reagents NO, O₂ and solvent 1,2-dichloro-ethane with ambient temperature for 24 hours. The yield is about 90%.

N-Methyl-4-nitroaniline is used to produce N-methyl-4-nitro-N-nitroso-aniline.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It is also toxic by inhalation, in contact with skin and if swallowed. What's more, it has danger of cumulative effects. During using it, wear suitable protective clothing, gloves and eye/face protection. After contact with skin, wash immediately. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CNC1=CC=C(C=C1)[N+](=O)[O-]
2. InChI: InChI=1S/C7H8N2O2/c1-8-6-2-4-7(5-3-6)9(10)11/h2-5,8H,1H3
3. InChIKey: XIFJZJPMHNUGRA-UHFFFAOYSA-N

Product Name

N-Methyl-4-nitroaniline

Synthetic route

N-Methyl-4-nitroaniline Specification

Related Products

Hot Products