ChemicalBook > CAS DataBase List > 3-Nitroaniline

3-Nitroaniline

Product Name: 3-Nitroaniline
CAS No.: 99-09-2
Chemical Name: 3-Nitroaniline
Synonyms: M-NITROANILINE;Benzenamine, 3-nitro-;Nitranilin;3-Nitroanilin;3-Nitrobenzenamine;1-AMINO-3-NITROBENZENE;ci37030;c.i.37030;3-Nitroani;azobasemna
CBNumber: CB8715335
Molecular Formula: C6H6N2O2
Formula Weight: 138.12
MOL File: 99-09-2.mol

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3-Nitroaniline Property

Melting point:: 111-114 °C (lit.)
Boiling point:: 306 °C
Density: 0,901 g/cm³
vapor pressure: 1 mm Hg ( 119 °C)
refractive index: 1.6396 (estimate)
Flash point:: 196 °C
storage temp.: Store below +30°C.
solubility: 1.25g/l
Colour Index: 37030
form: Crystals, Crystalline Powder and/or Chunks
pka: 2.466(at 25℃)
color: Yellow to ochre-yellow to orange
Specific Gravity: 0.901
Water Solubility: 1.25 g/L
Merck: 14,6581
BRN: 636962
Henry's Law Constant: 1.93 x 10^-5 atm?m³/mol at 25 °C (approximate - calculated from water solubility and vapor pressure)
CAS DataBase Reference: 99-09-2(CAS DataBase Reference)
NIST Chemistry Reference: m-Nitroaniline(99-09-2)
EPA Substance Registry System: m-Nitroaniline (99-09-2)

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Safety

Hazard Codes: T
Risk Statements: 23/24/25-33-52/53
Safety Statements: 28-36/37-45-61-28A
RIDADR: UN 1661 6.1/PG 2
WGK Germany: 2
RTECS: BY6825000
F: 8
Autoignition Temperature: 521℃
TSCA: Yes
HazardClass: 6.1
PackingGroup: II
HS Code: 29214210
Hazardous Substances Data: 99-09-2(Hazardous Substances Data)
Toxicity: Acute LD₅₀ for guinea pigs 450 mg/kg, mice 308 mg/kg, quail 562 mg/kg, rats 535 mg/kg (quoted, RTECS, 1985).

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P314Get medical advice/attention if you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: N9829
Product name: 3-Nitroaniline
Purity: 98%
Packaging: 5g
Price: $40.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: 45989
Product name: 3-Nitroaniline
Purity: analytical standard
Packaging: 250mg
Price: $37.4
Updated: 2022/05/15

TCI Chemical

Product number: N0117
Product name: 3-Nitroaniline
Purity: >98.0%(GC)
Packaging: 25g
Price: $58
Updated: 2025/07/31

TCI Chemical

Product number: N0117
Product name: 3-Nitroaniline
Purity: >98.0%(GC)
Packaging: 500g
Price: $459
Updated: 2025/07/31

Sigma-Aldrich

Product number: N9829
Product name: 3-Nitroaniline
Purity: 98%
Packaging: 500g
Price: $67.5
Updated: 2025/07/31

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3-Nitroaniline Chemical Properties,Usage,Production

Chemical Properties

3-Nitroaniline is a ochre-yellow to orange crystalline powder, crystallizes as yellow needles from water. It is moderately soluble in organic solvents and sparingly soluble in water (0.11 %).

Physical properties

Yellow, rhombic crystals or powder. Finely dispersered particles form explosive mixtures. Combustible.

Uses

Dyestuff intermediate. Acetylation of 3-nitroaniline followed by reduction gives 3-aminoacetanilide. Diazotization, followed by reduction of the diazosulfonate with ammonium bisulfite and subsequent hydrolysis, gives (3-nitrophenyl) hydrazine; an intermediate in the production of pyrazolone azo coupling components. 3-Nitroaniline is used as a diazo component (Fast Orange R Base) in azo dyes (e.g., C.I. Disperse Yellow 5 and C.I. Acid Orange 18).

Uses

3-Nitroaniline is commonly used as a raw material for dyes. It is also used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.

Production Methods

1,3-Dinitrobenzene is added to warm water containing magnesium sulfate. An aqueous solution of sodium hydrogen sulfide (6 molar equivalents) is added gradually to the vigorously stirred emulsion, and reduction is completed by heating to 90 ℃. The 3-nitroaniline produced solidifies on cooling and is separated by filtration.

Preparation

M-nitroaniline partial reduction.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 4992, 1980 DOI: 10.1021/jo01312a039
Tetrahedron Letters, 30, p. 251, 1989 DOI: 10.1016/S0040-4039(00)95173-6
Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013

General Description

Yellow needles or yellow powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Thermal stability of 3-Nitroaniline is reduced by various impurities. 3-Nitroaniline may be sensitive to prolonged exposure to light. 3-Nitroaniline may react explosively with ethylene oxide at 266° F. 3-Nitroaniline is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . Unstable when heated.

Hazard

Moderate fire risk. Toxic when absorbed by skin.

Fire Hazard

Flash point data for 3-Nitroaniline are not available; however, 3-Nitroaniline is probably combustible.

Synthesis

1,3-Dinitrobenzene is added towarmwater containing magnesium sulfate. An aqueous solution of sodium hydrogen sulfide (6molar equivalents) is added gradually to the vigorously stirred emulsion, and reduction is completed by heating to 90℃. The 3-nitroaniline produced solidifies on cooling and is separated by filtration.

Environmental Fate

Biological. A bacterial culture isolated from the Oconee River in North Georgia degraded 3- nitroaniline to the intermediate 4-nitrocatechol (Paris and Wolfe, 1987). A Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 3-nitroaniline as the sole source of carbon. However, in the presence of 4-nitroaniline, all of the applied 3-nitroaniline metabolized completely to carbon dioxide (Zeyer and Kearney, 1983). In the presence of suspended natural populations from unpolluted aquatic systems, the second-order microbial transformation rate constant determined in the laboratory was reported to be 4.6 ± 0.1 x 10^-13 L/organism?h (Steen, 1991).
In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976).
Chemical/Physical. Reacts with acids forming water soluble salts.

Purification Methods

Purify it as for o-nitroaniline. Warning: it is absorbed through the skin. [Beilstein 12 IV 1589.]

3-Nitroaniline Preparation Products And Raw materials

Raw materials

Sulfur CALCIUM SULFIDE Sodium sulfide Sodium sulfite SODIUM TETRASULFIDE Nitric acid Nitrobenzene Sulfuric acid 1,3-Dinitrobenzene

Preparation Products

1-(3-NITROPHENYL)-PIPERAZINE 4-hydroxy-1-methyl-3-[(3-nitrophenyl)azo]-2-quinolone 3-Fluoroaniline 3-NITROBIPHENYL N1-(3-Aminophenyl)acetamide 3-Nitrophenol Disperse Red 74 Mordant Yellow 1 Disperse Red S-2GFL 3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide 5-Aminoquinoline N-(3-Aminophenyl)methanesulfamide 3'-NITROACETANILIDE 3-Bromoaniline 1,3-Difluorobenzene

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