99-59-2

Basic information

• Product Name: 2-Amino-4-nitro anisidine
• Synonyms: 1-Amino-2-methoxy-5-nitrobenzene;1-Methoxy-2-amino-4-nitrobenzene;2-methoxy-5-nitro-anilin;2-Methoxy-5-nitrobenzamine;2-methoxy-5-nitro-benzenamin;2-Methoxy-5-nitrobenzenamine;2-methoxy-5-nitro-Benzenamine;3-Amino-4-methoxynitrobenzene
• CAS NO: 99-59-2
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15
• EINECS: 202-770-5
• Product Categories: Intermediates of Dyes and Pigments;Amines;Building Blocks;C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 99-59-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: 117-119 °C(lit.)
• Boiling Point: 337.07°C (rough estimate)
• Flash Point: 119℃
• Appearance: orange to brown powder
• Density: 1.2068
• Vapor Pressure: 0.04Pa
• Refractive Index: 1.6010 (estimate)
• Solubility: 382mg/L in organic solvents at 20 ℃
• PKA: 2.42±0.10(Predicted)
• Water Solubility: Slightly soluble.
• Stability: Stable, but may be moisture sensitive. Incompatible with water, acids, strong oxidizing agents, acid chlorides, acid anhydrides,
• BRN: 879620
• CAS DataBase Reference: 2-Amino-4-nitro anisidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-nitro anisidine(99-59-2)
• EPA Substance Registry System: 2-Amino-4-nitro anisidine(99-59-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-45-36/37
• WGK Germany: 2
• RTECS: BZ7175000
• TSCA: Yes
• Hazardous Substances Data: 99-59-2(Hazardous Substances Data)

Usage

Chemical Properties

5-Nitro-o-anisidine is an orange-red crystalline compound.

Uses

2-Methoxy-5-nitroaniline was used in the synthesis of 5-(9-acridinylamino)-p-anisidines via reaction with 9-anilinoacridines. It was also used in the synthesis of disazo disperse dyes containing nitro and methoxy groups, used for the dyeing of polyester fibre.

General Description

Orange-red needles or orange powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Amino-4-nitro anisidine is incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides and chloroformates .

Fire Hazard

Flash point data for 2-Amino-4-nitro anisidine are not available. 2-Amino-4-nitro anisidine is probably combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Potential Exposure

5-Nitro-o-anisidine is a chemical intermediate in the production of C.I. Pigment red 23, which is used as a colorant for commodities, such as printing inks, interior latex paints; lacquers, rubber, plastics, floor coverings; paper coating; and textiles. It is also used with other C.I. coupling components to produce various hues of red, brown, yellow, and violet on cotton, silk, acetate and nylon.

Waste Disposal

Incineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement.

InChI:InChI=1/C7H8N2O3/c1-12-7-3-2-5(9(10)11)4-6(7)8/h2-4H,8H2,1H3

Upstream product

• 93-26-5 2-methoxyacetanilide 
• 90-04-0 2-methoxy-phenylamine 
• 455-93-6 2-fluoro-1-methoxy-4-nitrobenzene 
• 119-27-7 2,4-dinitroanisole 
• 121-44-8 triethylamine 
• 7647-01-0 hydrogenchloride 
• 136833-44-8 2-nitro-4-amino-5-methoxybenzoic acid 
• 100-17-4 para-methoxynitrobenzene 
• 67827-72-9 2-methoxy-5-nitroaniline hydrochloride 
• 13027-36-6 N-hydroxy-2-methoxy-5-nitroaniline 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 100-66-3 methoxybenzene 
• 89-41-8 4-methoxy-3-nitrobenzoic acid 
• 10496-75-0 2-methoxy-5-nitrobenzylnitrile 

Downstream Products

• 66095-84-9 N,N-bis-(2-hydroxy-ethyl)-2-methoxy-5-nitro-aniline 
• 33721-54-9 N-(2-methoxy-5-nitrophenyl)acetamide 
• 13142-91-1 N-(2-methoxy-5-nitrophenyl)-N'-phenyl-urea 
• 330469-45-9 isobutyric acid-(2-methoxy-5-nitro-anilide) 
• 63379-21-5 (2-methoxy-5-nitro-phenyl)-carbamic acid methyl ester 
• 301172-87-2 toluene-4-sulfonic acid-(2-methoxy-5-nitro-anilide) 
• 17012-47-4 8-methoxy-5-nitroquinoline 
• 32895-23-1 N¹-(2-Methoxy-5-nitrophenyl)-N⁴-acetyl-sulfanylamid 
• 59741-17-2 2-methoxy-5-nitrophenyl isocyanate 
• 71793-51-6 2-methoxy-5-nitrophenyl isothiocyanate 
• 100-17-4 para-methoxynitrobenzene 
• 21193-39-5 N-(2-methoxy-5-nitrophenyl)anthranilic acid 
• 7501-46-4 N,N-dimethyl-2-methoxy-5-nitroaniline 
• 855937-11-0 acetic acid-(2-methoxy-4-methyl-5-nitro-anilide) 

Relevant articles and documents

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Pyrroloquinoline quinone synthetic method

The invention discloses a synthetic method of pyrroloquinoline quinone. The synthetic method comprises the following steps: carrying out alkali treatment on 2-methoxy-5-nitroaniline hydrochloride as a raw material, so as to obtain a compound 1; carrying out formylation on the compound 1 under a catalysis condition of an ionic liquid, so as to obtain a compound 2; adopting sodium borohydride to reduce the compound 2 to obtain a compound 3; carrying out diazotization on the compound 3, and then enabling action between the diazotized compound 3 and HBF4 to obtain a compound 4; enabling reaction of the compound 4 and 2-methylethyl acetoacetate to obtain a compound 5; treating the compound 5 with formic acid to obtain a compound 6; carrying out amid catalysis and exchange with the ionic liquid on the compound 6 to obtain a compound 7; enabling reaction of the compound 7 and 2-oxodimethyl glutaconate to obtain a compound 8; feeding hydrogen chloride to the compound 8 under the action of Cu(OAc)2*2H2O to obtain a compound 9; carrying out basic hydrolysis on the compound 9 to obtain a compound 10. The synthetic method disclosed by the invention is cheap and accessible in raw materials, stable, high in reaction yield, quick in reaction, and easy for product separation, and is environment-friendly as the catalyst can be recycled.

Selective partial hydrogenation of dinitrobenzenes to nitroanilines catalyzed by Ru/C

Ru/C was found to be a highly effective catalyst for the selective partial hydrogenation of a range of dinitrobenzenes to their corresponding nitroanilines with excellent selectivity under mild conditions. Furthermore, the effect from other substitute groups of dinitrobenzenes on partial hydrogenation was also explored in this study. Copyright