N-Methyl-4-nitroaniline
Basic information
- CAS
100-15-2- Standard SMILES
CNc1ccc([N+](=O)[O-])cc1- InChIKey
XIFJZJPMHNUGRA-UHFFFAOYSA-N- Molecular formula
- C7H8N2O2
- Average molar mass
- 152.15 g/mol
- Monoisotopic mass
- 152.0585775
Overview
N-methyl-4-nitroaniline appears as brownish-yellow prisms with violet reflex (from ethanol) or yellow powder. (NTP, 1992)
Names & identifiers
- Preferred name
- N-Methyl-4-nitroaniline
- IUPAC
- N-methyl-4-nitroaniline
- English name
- N-Methyl-4-nitroaniline
- Molecular formula
- C7H8N2O2
- Molecular weight
- 152.15
Names & synonyms
N-Methyl-4-nitroaniline100-15-2Benzenamine, N-methyl-4-nitro-N-Methyl-p-nitroaniline4-Nitro-N-methylanilineN-Methyl-p-nitranilinep-Nitro-N-methylanilinep-(Methylamino)nitrobenzeneN-Monomethyl-p-nitroanilineAniline, N-methyl-p-nitro-N-METHYL-4-NITROBENZENAMINEmethyl(4-nitrophenyl)amine
Show more names
NitronanilineMethyl-4-nitroanilineN-methy-4-nitroanlineIntedanib Impurity 10Miglinide intermediate
DTXSID70256354-(Methylamino)nitrobenzeneJ836WLV9BWNSC-5390DTXCID605635RefChem:163712N-methyl-para-nitroaniline202-823-2
Database identifiers
- CAS
100-15-2- PubChem CID
- 7483
- DTXSID
DTXSID7025635- ChEMBL
CHEMBL1329734- UNII
- J836WLV9BW
- EC Number
- 202-823-2
- Nikkaji
- J37.757K
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 57.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 136
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitroanilines
SpringerMaterials PropertiesDensity
LogP1.98
Density1.201 at 311 °F (NTP, 1992) - Denser than water; will sink
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)
Boiling PointDecomposes (NTP, 1992)
Melting Point306 °F (NTP, 1992)
Vapor Pressure0.00764 [mmHg]
Physical Description
N-methyl-4-nitroaniline appears as brownish-yellow prisms with violet reflex (from ethanol) or yellow powder. (NTP, 1992)
CBI
Brownish-yellow or yellow solid; [CAMEO] Yellow crystalline powder; [Alfa Aesar MSDS]
Physicochemical properties
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 56 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenamine, N-methyl-4-nitro-
Benzenamine, N-methyl-4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N-methyl-4-nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: N-methyl-4-nitroaniline (EC: 202-823-2)
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: This chemical may cause irritation.
Hazards SummaryMay cause irritation; [NTP] May cause irritation; May induce methemoglobinemia; Toxic by ingestion, inhalation, and skin absorption; May have cumulative adverse effects to organs; [Alfa Aesar MSDS] See p-Nitroaniline.
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity Profile
Chemistry & industry
Uses & manufacturing
U.S. Production2023: <50,000 lb
Industry UsesStabilizing agent
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
Benzenamine, N-methyl-4-nitro-: ACTIVE
Applications
UsesN-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.
UsesN-Methyl-4-nitroaniline is a versatile reactant used in the synthesis of oxindoles using Pd-catalyzed cyclization of chloroacetanilides.
General DescriptionBrownish-yellow prisms with violet reflex (from ethanol) or yellow powder.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
61 records
Compound notes
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