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| CAS No.: | 88-74-4 |
|---|---|
| Name: | 2-Nitroaniline |
| Article Data: | 299 |
| Molecular Structure: | |
|
|
|
| Formula: | C6H6N2O2 |
| Molecular Weight: | 138.126 |
| Synonyms: | Aniline,o-nitro- (8CI);1-Amino-2-nitrobenzene;1-Nitro-2-aminobenzene;2-Aminonitrobenzene;2-Nitrobenzenamine;2-Nitrophenylamine;Azoene Fast Orange GR Base;Azoene Fast Orange GR Salt;Azofix Orange GR Salt;Azogene Fast Orange GR;Brentamine Fast Orange GR Base;Brentamine Fast OrangeGR Salt;Devol Orange B;Devol Orange Salt B;Fast Orange Base JR;Fast OrangeGR Base;Fast Orange O Base;Fast Orange O Salt;Fast Orange Salt JR;HiltonilFast Orange GR Base;o-Nitroaniline;Hindasol Orange GR Salt;NSC9796;Natasol Fast Orange GR Salt;ONA;Orange Base Ciba II;Orange Base IrgaII;Orange GRS Salt;Orange Salt Ciba II;Orange Salt Irga II;o-Aminonitrobenzene;o-Nitrobenzenamine;o-Nitrophenylamine; |
| EINECS: | 201-855-4 |
| Density: | 1.333 g/cm3 |
| Melting Point: | 70-73 °C(lit.) |
| Boiling Point: | 284.9 °C at 760 mmHg |
| Flash Point: | 126.1 °C |
| Solubility: | 1.1 g/L (20 °C) in water |
| Appearance: | orange solid |
| Hazard Symbols: |
 T,  F
|
| Risk Codes: | 23/24/25-33-52/53-39/23/24/25-11 |
| Safety: | 28-36/37-45-61-28A-16-7 |
| Transport Information: | UN 1661 6.1/PG 2 |
| PSA: | 71.84000 |
| LogP: | 2.28140 |
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
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- 90221-55-92-bromo-5-methylbenzaldehyde
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- 926293-55-26-Bromo-2-methylpyridine-3-carboxaldehyde
- 911112-05-55-Iodo-3-(trifluoromethyl)-2-pyridinamine
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| Conditions | Yield |
|---|---|
| With iron(II) sulfate In water; dimethyl sulfoxide Ambient temperature; | 100% |
| With HbO2(2+) In phosphate buffer; dimethyl sulfoxide for 1h; pH=7.4; | 89 % Chromat. |
| Conditions | Yield |
|---|---|
| With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 5.5h; Inert atmosphere; | 99% |
| Conditions | Yield |
|---|---|
| With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr; | 98.6% |
| With ammonium hydroxide at 150 - 220℃; under 90009 - 150015 Torr; | 98% |
| With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h; | 95% |
| Conditions | Yield |
|---|---|
| With hydrogen at 20℃; under 760.051 Torr; for 1h; | 98% |
| With hydrogen; 1-(2-benzimidazolyl)-C(CH3)=NH-NHCSNH2-Pd(II) In tetrahydrofuran at 20℃; for 2h; atmospheric pressure; | 95% |
| With triethylamine In water at 80℃; for 2h; Inert atmosphere; Green chemistry; chemoselective reaction; | 95% |
| Conditions | Yield |
|---|---|
| With 1-n-butyl-3-methylimidazolium azide; sulfuric acid; acetic acid at 54℃; for 4h; Schmidt Reaction; | 97% |
| With sodium azide; chloroform; sulfuric acid | |
| With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 2h, reflux; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 0.5h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 95% |
| With sodium hydroxide In ethanol Reflux; | 80% |
| With hydrogenchloride; water for 2h; Reflux; | 77% |
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 6h; Reagent/catalyst; Time; Sealed tube; Inert atmosphere; | 95% |
| Stage #1: 2-nitrophenyl bromide With copper(l) iodide; D-glucosamine hydrochloride; potassium carbonate In water; acetone at 90℃; for 0.166667h; Stage #2: With ammonia In water; acetone at 90℃; for 24h; | 83% |
| With ammonium hydroxide; copper(l) iodide; potassium carbonate; 4R-4-hydroxyproline In dimethyl sulfoxide at 70℃; for 24h; | 78% |
| Conditions | Yield |
|---|---|
| With 1,9-diperoxynonanedioic acid In acetonitrile at 50℃; for 0.5h; Reagent/catalyst; | 95% |
| With dihydrogen peroxide; acetonitrile In aq. buffer at 20℃; for 20h; pH=11; Green chemistry; | 86% |
| With dihydrogen peroxide; potassium carbonate In water; acetonitrile at 20℃; | 75% |
| With sodium peroxide | |
| palladium-carbon In triethylene glycol dimethyl ether |
| Conditions | Yield |
|---|---|
| Stage #1: o-azidonitrobenzene With hydrazine hydrate for 0.166667h; Inert atmosphere; Stage #2: for 4h; Catalytic behavior; Reagent/catalyst; Irradiation; chemoselective reaction; | 95% |
| With methanol; sodium tetrahydroborate In tetrahydrofuran for 1h; Heating; | 94% |
| Stage #1: o-azidonitrobenzene With 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride; tert-butyl alcohol In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With sodium t-butanolate In tetrahydrofuran at 20℃; for 5h; Inert atmosphere; chemoselective reaction; | 94% |
| Conditions | Yield |
|---|---|
| With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 1h; Product distribution; Further Variations:; Solvents; reaction time; Heating; | 95% |
| With lithium aluminium tetrahydride In diethyl ether at 27℃; for 1h; | 66 % Turnov. |
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Chemistry
IUPAC Name: 2-Nitroaniline
Synonyms of o-Nitroaniline (CAS NO.88-74-4): Aniline, o-nitro- ; Benzenamine, 2-nitro- ; o-Nitroaniline ; UN1661 ; o-Nitroaniline [UN1661] [Poison]
CAS NO: 88-74-4
Classification Code: Mutation data
Molecular Formula: C6H6N2O2
Molecular Weight: 138.124
Molecular Structure:
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Melting Point: 70-73 °C
Polar Surface Area: 71.84 Å2
Index of Refraction: 1.634
Molar Refractivity: 37.03 cm3
Molar Volume: 103.5 cm3
Surface Tension: 60.3 dyne/cm
Density: 1.333 g/cm3
Flash Point: 126.1 °C
Enthalpy of Vaporization: 52.4 kJ/mol
Boiling Point: 284.9 °C at 760 mmHg
Vapour Pressure: 0.00289 mmHg at 25°C
Uses
o-Nitroaniline (CAS NO.88-74-4) is rubber antioxidant MB, pesticides carbendazim, light stabilizer UV-P intermediates.It can be used as the goods azoic dyes for color-based (orange-GC), and other dye intermediates, can be used to hand Cotton fabric dyeing, the system could Color Yield amylin.
Production
Adding ortho-nitrochlorobenzene into the filled with a certain concentration of ammonia Autoclave at 185-190 °C, 4-4.5 MPa for ammonia solution, o-nitroaniline crude via cooling and crystallization, filtration, derived products.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| bird - wild | LD50 | oral | 750mg/kg (750mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
| guinea pig | LD50 | oral | 2350mg/kg (2350mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 89, 1966. |
| mammal (species unspecified) | LD50 | unreported | 9441mg/kg (9441mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(6), Pg. 22, 1983. | |
| mouse | LD50 | oral | 1070mg/kg (1070mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981. | |
| quail | LD50 | oral | 750mg/kg (750mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
| rat | LC50 | inhalation | > 2529mg/m3/4H (2529mg/m3) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | National Technical Information Service. Vol. OTS0558766, |
| rat | LD50 | oral | 1600mg/kg (1600mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Voprosy Kommunal'noi Gigieny. Problems of Communal Hygiene. Vol. 6, Pg. 89, 1966. |
| rat | LDLo | intraperitoneal | 800mg/kg (800mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 91, 1982. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Hazard Symbols of o-Nitroaniline (CAS NO.88-74-4): 
T
Risk Codes: 23/24/25-33-52/53-39-11
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R33:Danger of cumulative effects.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
R39:Danger of very serious irreversible effects.
R11:Highly flammable.
Safety Description: S28;S36/37;S45;S61
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.
Transport Information: UN 1661
A poison. Moderately toxic by ingestion. Mildly toxic by skin contact. Mutation data reported. Mixtures with magnesium are hypergolic on contact with nitric acid. Forms extremely explosive addition compounds with hexanitroethane. Vigorous reaction with sulfuric acid above 200°C. When heated to decomposition it emits toxic fumes of NOx. See also m-NITROANILINE, p-NITROANILINE, and ANILINE DYES.
Standards and Recommendations
DOT Classification: 6.1; Label: Poison
Specification
Handling: Do not get in eyes, on skin, or on clothing. Do not breathe vapor. Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only with adequate ventilation or respiratory protection.
Storage: Store protected from light. Store in a cool, dry, well-ventilated area away from incompatible substances. Store in a tightly closed container.