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88-74-4

Basic Information
CAS No.: 88-74-4
Name: 2-Nitroaniline
Article Data: 299
Molecular Structure:
Molecular Structure of 88-74-4 (2-Nitroaniline)
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: ToxicT, FlammableF
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
Synthetic route
480-96-6

benzofurazan oxide

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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.
6380-13-8

4-methyl-N-(2-nitrophenyl)benzene sulfonamide

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 25 - 90℃; for 5.5h; Inert atmosphere;99%
88-73-3

2-Chloronitrobenzene

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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%
528-29-0

1,2-Dinitrobenzene

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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%
552-16-9

ortho-nitrobenzoic acid

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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;
552-32-9

o-nitroacetanilide

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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%
577-19-5

2-nitrophenyl bromide

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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%
95-54-5

1,2-diamino-benzene

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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
1516-58-1

o-azidonitrobenzene

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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%
728-90-5

N-(2-nitrophenyl)benzanilide

88-74-4

2-nitro-aniline

Conditions
ConditionsYield
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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    CAS:88-74-4 EINECS:201-855-4 MW:138.12 MF:C6H6N2O2 Melting point:70-73 °C(lit.) Boiling point:284 °C(lit.) Appearance:orange needle crystal Package:25kg/drum Transportation:by sea/air/courier Port:Shanghai

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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:

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): ToxicT  
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.