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N-Methyl-4-nitroaniline

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Name

N-Methyl-4-nitroaniline

EINECS 202-823-2
CAS No. 100-15-2 Density 1.26 g/cm3
PSA 57.85000 LogP 2.23270
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 Molecular Structure of 100-15-2 (N-Methyl-4-nitroaniline) Hazard Symbols ToxicT,IrritantXi
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;

Article Data 153

N-Methyl-4-nitroaniline Synthetic route

10252-27-4

p-Nitrophenyl-N-methyl-carbamidsaeure-methylester

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;
123-39-7

N-Methylformamide

100-00-5

4-chlorobenzonitrile

100-15-2

N-methyl(p-nitroaniline)

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

p-nitrobenzene iodide

74-89-5

methylamine

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%
100-01-6

4-nitro-aniline

74-88-4

methyl iodide

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℃;
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
ConditionsYield
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
ConditionsYield
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
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
100-00-5

4-chlorobenzonitrile

74-89-5

methylamine

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

350-46-9

4-Fluoronitrobenzene

100-15-2

N-methyl(p-nitroaniline)

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

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

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