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Home > Encyclopedia > N-Methyl-4-nitroaniline

N-Methyl-4-nitroaniline

N-Methyl-4-nitroaniline structure

N-Methyl-4-nitroaniline 

structure
  • CAS No:

    100-15-2

  • Formula:

    C7H8N2O2

  • Chemical Name:

    N-Methyl-4-nitroaniline

  • Synonyms:

    Benzenamine,N-methyl-4-nitro-;Aniline,N-methyl-p-nitro-;N-Methyl-4-nitrobenzenamine;N-Monomethyl-p-nitroaniline;N-Methyl-p-nitroaniline;N-Methyl-4-nitroaniline;p-(Methylamino)nitrobenzene;N-Methyl-p-nitraniline;4-Nitro-N-methylaniline;p-Nitro-N-methylaniline;4-(Methylamino)nitrobenzene;Methyl(4-nitrophenyl)amine;NSC 5390;N-(4-Nitrophenyl)-N-methylamine

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

Description

brownish-yellow crystalline powderBrownish-yellow prisms with violet reflex (from ethanol) or yellow powder.


N-methyl-4-nitroaniline appears as brownish-yellow prisms with violet reflex (from ethanol) or yellow powder. (NTP, 1992)


N-methyl-4-nitroaniline appears as brownish-yellow prisms with violet reflex (from ethanol) or yellow powder. (NTP, 1992)

N-Methyl-4-nitroaniline Basic Attributes

152.15

152.15

637920

202-823-2

5390

1661

DTXSID7025635

29214200

Characteristics

57.8

2

N-methyl-4-nitroaniline appears as brownish-yellow prisms with violet reflex (from ethanol) or yellow powder. (NTP, 1992)

1.201 at 311° F (NTP, 1992)

152 °C

294.61°C (rough estimate)

129.5ºC

1.6276 (estimate)

H2O: <0.1 g/100 mL at 19 ºC

Keep containers tightly closed. Store in a cool, dry area away from incompatible substances.

0.00205mmHg at 25°C

5.25 (vs air)

This chemical may be sensitive to prolonged exposure to air. Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

N-METHYL-4-NITROANILINE has a vigorous exothermic reaction with carbaryl sulfate when heated above 167° F. (NTP, 1992)

Safety Information

III

6.1

2811

3

23/24/25-33-36/37/38

28-36/37/39-45-26

T,Xi

Highly Toxic/Irritant

Stable. Combustible. Incompatible with strong oxidizing agents.

P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501

H301

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should keep this material in a tightly closed container under an inert atmosphere, and store it at refrigerated temperatures. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Drug Information

SYMPTOMS: This chemical may cause irritation. ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits toxic fumes of nitrogen oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

N-methyl-4-nitroaniline

N-Methyl-4-nitroaniline Use and Manufacturing

Methods of Manufacturing

It is made from p-nitroacetanilide, methyl iodide and ethanol as raw materials. Mix acetone, p-nitroacetanilide, and potassium hydroxide, heat and reflux, and dropwise add iodine solution in acetone. After addition, continue to reflux for 4h. After standing overnight, crystals were precipitated after recovery of acetone. After cold washing, the alkali was washed and washed with ethanol to obtain N-methyl-p-nitroacetanilide. Then mix it with ethanol and hydrochloric acid, heat to reflux for 8h, recover ethyl acetate and ethanol, then dilute in water, wash away the acidity, and dry to obtain the crude product. Dissolve the crude product with acetone, filter, and recover the acetone to precipitate the crystal as the finished product.

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.

Benzenamine, N-methyl-4-nitro-: ACTIVE

Computed Properties

Molecular Weight:152.15
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:152.058577502
Monoisotopic Mass:152.058577502
Topological Polar Surface Area:57.8
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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