578-46-1

Basic information

• Product Name: 5-METHYL-2-NITROANILINE
• Synonyms: 6-NITRO-M-TOLUIDINE;5-METHYL-2-NITROANILINE;3-AMINO-4-NITROTOLUENE;3-METHYL-6-NITROANILINE;LABOTEST-BB LTBB000630;3-methyl-6-nitro-benzenamin;6-nitro-m-toluidin;5-Methyl-2-nitro phenylamine
• CAS NO: 578-46-1
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• EINECS: 209-423-7
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Amines;Bioactive Small Molecules;Building Blocks;C7;Cell Biology;Chemical Synthesis;M;Nitrogen Compounds;Organic Building Blocks
• Mol File: 578-46-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 110-111 °C(lit.)
• Boiling Point: 312.4 °C at 760 mmHg
• Flash Point: 142.8 °C
• Appearance: /
• Density: 1.269 g/cm³
• Vapor Pressure: 0.000529mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.03±0.25(Predicted)
• BRN: 2691416
• CAS DataBase Reference: 5-METHYL-2-NITROANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYL-2-NITROANILINE(578-46-1)
• EPA Substance Registry System: 5-METHYL-2-NITROANILINE(578-46-1)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-36/37-45-61
• RIDADR: UN 2660 6.1/PG 3
• WGK Germany: 3
• RTECS: XU8060000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 578-46-1(Hazardous Substances Data)

Usage

Uses

5-Methyl-2-nitroaniline has been used in the preparation of N-(5-methyl-2-nitrophenyl)-4-[N-(pyridin-3-ylmethoxy carbonyl)aminomethyl]benzamide.

General Description

Yellow leaflets (from water) or orange powder.

Air & Water Reactions

5-METHYL-2-NITROANILINE is sensitive to prolonged exposure to air. Insoluble in water.

Reactivity Profile

5-METHYL-2-NITROANILINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates, and strong oxidizers .

Health Hazard

SYMPTOMS: Symptoms of exposure to 5-METHYL-2-NITROANILINE may include irritation. Structurally similar chemicals may cause methemoglobinemia.

Fire Hazard

Flash point data for 5-METHYL-2-NITROANILINE are not available; however, 5-METHYL-2-NITROANILINE is probably combustible.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C7H8N2O2/c1-5-2-3-7(9(10)11)6(8)4-5/h2-4H,8H2,1H3

Upstream product

• 610-39-9 3,4-Dinitrotoluene 
• 19164-41-1 5-methylbenzofuroxan 
• 38512-82-2 3-methoxy-4-nitrotoluene 
• 7664-41-7 ammonia 
• 7647-01-0 hydrogenchloride 
• 700-38-9 2-nitro-5-methylphenol 
• 102871-93-2 2-ethoxy-4-methyl-1-nitrobenzene 
• 108-44-1 1-amino-3-methylbenzene 
• 7418-36-2 N-(5-methyl-2-nitrophenyl)acetamide 
• 7664-93-9 sulfuric acid 
• 601-87-6 3-methyl-2-nitroaniline 
• 25917-89-9 4-amino-3-nitro-6-methylaniline 
• 537-92-8 3-Methylacetanilide 

Downstream Products

• 7418-36-2 N-(5-methyl-2-nitrophenyl)acetamide 
• 343617-23-2 toluene-4-sulfonic acid-(5-methyl-2-nitro-anilide) 
• 827-32-7 4-bromo-5-methyl-2-nitrophenylamine 
• 335349-58-1 4-iodo-5-methyl-2-nitroaniline 
• 190139-57-2 isopropylidene (5-methyl-2-nitroanilino)methylenemalonate 
• 65081-42-7 3-(N-methylamino)-4-nitrotoluene 
• 1025886-13-8 N-(5-methyl-2-nitrophenyl)-4-benzamide 
• 859807-50-4 (5-methyl-2-nitro-phenyl)-carbamic acid ethyl ester 
• 38939-88-7 2-chloro-4-methyl-1-nitrobenzene 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 52488-29-6 2-iodo-4-methyl-1-nitrobenzene 
• 40385-54-4 3-bromo-4-nitrotoluene 
• 610-39-9 3,4-Dinitrotoluene 
• 109469-94-5 2-(5-methyl-2-nitro-phenyl)-benz[de]isoquinoline-1,3-dione 

Relevant articles and documents

The reduction of benzofuroxans by ferrous salts and by thiophenol

Treatment of benzofuroxan derivatives with ferrous sulphate in DMSO/water solution affords in high yield o-nitroanilines. o-Nitroaniline was also obtained by reduction of benzofuroxan with thiophenol in presence of catalytic amount of Fe2+ or Fe3+ salts.

Nitroanilines are the reduction products of benzofuroxan system by oxyhemoglobin (HbO22+)

Benzofuroxans are interesting compounds which display several biochemical and pharmacological properties. Recent studies from our laboratory demonstrate that they are reduced by ferrous salts at room temperature and that the principal reaction products are o-nitroanilines. This paper shows that simple benzofuroxan derivatives are also able to oxidise HbO22+ to methemoglobin (MetHb3+) (UV detection) and to form o-nitroanilines (HPLC detection). From a toxicological point of view this reaction is interesting, since it indicates that the blood is a site for metabolism of these compounds with consequent methemoglobinemia and formation of toxic compounds.

The Rearragement of Aromatic Nitro Compounds. Part 1. The Reactions of Nitroanilines in Aqueous Sulphuric Acid

A number of substituted 2-nitroanilines rearange in concentrated sulphuric acid at 110 deg C to yield products that appear to be derived from 1,3-migration of the 2-nitro-group.For 2,3-dinitroaniline, the rate of reaction is almost independent of acidity over the range 83-97percent sulphuric acid and the solvent isotope effect k(H2SO4)/k(D2SO4) is 1.3-1.9.Methyl and t-butyl groups, when present as additional substituents in 2,3-dinitroaniline, have only a small effect on the reaction rate but 3-methyl-2-nitroaniline reacts much more slowly than 2,3-dinitroaniline.These results are discussed in terms of a rate-determining migration of the 2-nitro group following protonation at the 2-position.