ChemicalBook Product Catalog Organic Chemistry Amides Naphthenic amines derivatives N-Methyl-4-nitroaniline

N-Methyl-4-nitroaniline

Product NameN-Methyl-4-nitroaniline
CAS100-15-2
MFC7H8N2O2
MW152.15
EINECS202-823-2
MOL File100-15-2.mol

Chemical Properties

Melting point	149-151 °C(lit.)
Boiling point	294.61°C (rough estimate)
Density	1.2010
vapor density	5.25 (vs air)
refractive index	1.6276 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	0.56±0.12(Predicted)
color	Yellow to Very Dark Yellow
Water Solubility	<0.1 g/100 mL at 19 ºC
BRN	637920
Stability	Stable. Combustible. Incompatible with strong oxidizing agents.
InChI	1S/C7H8N2O2/c1-8-6-2-4-7(5-3-6)9(10)11/h2-5,8H,1H3
InChIKey	XIFJZJPMHNUGRA-UHFFFAOYSA-N
SMILES	CNc1ccc(cc1)[N+]([O-])=O
CAS DataBase Reference	100-15-2(CAS DataBase Reference)
NIST Chemistry Reference	Benzenamine, N-methyl-4-nitro-(100-15-2)
EPA Substance Registry System	N-Methyl-p-nitroaniline (100-15-2)

Safety Information

Hazard Codes	T,Xi
Risk Statements	23/24/25-33-36/37/38
Safety Statements	28-36/37/39-45-26
RIDADR	2811
WGK Germany	3
Hazard Note	Highly Toxic/Irritant
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29214200
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Chronic 3 STOT RE 2

MSDS

Provider	Language
4-Nitro-N-methylaniline	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Uses

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.

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

Uses

N-Methyl-4-nitroaniline is a versatile reactant used in the synthesis of oxindoles using Pd-catalyzed cyclization of chloroacetanilides.

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.]

Preparation Products And Raw materials