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Cas Database

88-74-4

88-74-4

Identification

  • Product Name:2-Nitroaniline

  • CAS Number: 88-74-4

  • EINECS:201-855-4

  • Molecular Weight:138.126

  • Molecular Formula: C6H6N2O2

  • HS Code:29214210

  • Mol File:88-74-4.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT, FlammableF

  • Hazard Codes:T,F

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H331 Toxic if inhaled H373 May cause damage to organs through prolonged or repeated exposure H412 Harmful to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . Inhalation or ingestion causes headache, nausea, methemo- globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion. (USCG, 1999) INHALATION: Fresh air, rest. Artificial respiration if indicated. Refer for medical attention. SKIN: Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention. EYES: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor.

  • Fire-fighting measures: Suitable extinguishing media Extinguish with water, dry chemicals, foam or carbon dioxide. Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. 1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container & burn in a safe place (such as a fume hood). Large quantities may be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alcohol) & atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong acids, strong oxidants, combustible substances, reducing agents and food and feedstuffs.Protect against physical damage to containers and prevent from moisture contacts.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
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  • Product Description:2-Nitroaniline >99.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Nitroaniline for synthesis. CAS No. 88-74-4, EC Number 201-855-4., for synthesis
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  • Product Description:2-Nitroaniline 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Nitroaniline for synthesis. CAS No. 88-74-4, EC Number 201-855-4., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Nitroaniline 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:2-Nitroaniline 98%
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Relevant articles and documentsAll total 192 Articles be found

Virtual Transition State for the Acylation Step of Acetylcholinesterase-Catalysed Hydrolysis of o-Nitrochloroacetanilide

Quinn, Daniel M.,Swanson, Michael L.

, p. 1883 - 1884 (1984)

-

-

Boyer et al.

, (1957)

-

-

Tocco,D.J. et al.

, p. 399 - 405 (1964)

-

Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines

Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju

supporting information, p. 1915 - 1923 (2021/02/06)

Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.

Discovery and development of 2-aminobenzimidazoles as potent antimalarials

Avery, Vicky M.,Challis, Matthew P.,Creek, Darren J.,De Paoli, Amanda,Devine, Shane M.,Kigotho, Jomo K.,MacRaild, Christopher A.,Norton, Raymond S.,Scammells, Peter J.,Siddiqui, Ghizal

, (2021/06/03)

The emergence of Plasmodium falciparum resistance to frontline antimalarials, including artemisinin combination therapies, highlights the need for new molecules that act via novel mechanisms of action. Herein, we report the design, synthesis and antimalarial activity of a series of 2-aminobenzimidazoles, featuring a phenol moiety that is crucial to the pharmacophore. Two potent molecules exhibited IC50 values against P. falciparum 3D7 strain of 42 ± 4 (3c) and 43 ± 2 nM (3g), and high potency against strains resistant to chloroquine (Dd2), artemisinin (Cam3.IIC580Y) and PfATP4 inhibitors (SJ557733), while demonstrating no cytotoxicity against human cells (HEK293, IC50 > 50 μM). The most potent molecule, possessing a 4,5-dimethyl substituted phenol (3r) displayed an IC50 value of 6.4 ± 0.5 nM against P. falciparum 3D7, representing a 12-fold increase in activity from the parent molecule. The 2-aminobenzimidazoles containing a N1-substituted phenol represent a new class of molecules that have high potency in vitro against P. falciparum malaria and low cytotoxicity. They possessed attractive pharmaceutical properties, including low molecular weight, high ligand efficiency, high solubility, synthetic tractability and low in vitro clearance in human liver microsomes.

Magnetically‐recoverable Schiff base complex of Pd(II) immobilized on Fe3O4@SiO2 nanoparticles: an efficient catalyst for the reduction of aromatic nitro compounds to aniline derivatives

Azadi, Sedigheh,Esmaeilpour, Mohsen,Sardarian, Ali Reza

, p. 809 - 821 (2021/07/20)

Fe3O4@SiO2/Schiff base/Pd(II) is reported as a magnetically recoverable heterogeneous catalyst for the chemoselective reduction of aromatic nitro compounds to the corresponding amines through catalytic transfer hydrogenation (CTH). In this regard, a small amount of the nanocatalyst (0.52?mol% Pd) and hydrazine hydrate, showing safe characteristics and perfect ability as the hydrogen donor, were added to the nitro substrates. The experiments described the successful reduction of aromatic nitro compounds with good to excellent yields and short reaction times. The catalyst, due to its magnetic property, could be simply separated from the reaction mixture by a permanent magnet and reused in seven consecutive reactions without considerable loss in its activity. Moreover, the leaching of Pd was only 3.6% after the seventh run. Thus, the most striking feature of this method is to use a small amount of the magnetic nanocatalyst along with a cheap and safe hydrogen source to produce the important amine substances selectively, which makes the method economical, cheap, environmentally friendly, and simple. Graphic abstract: [Figure not available: see fulltext.]

A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride

Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.

supporting information, p. 3565 - 3589 (2021/10/12)

The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.

Copper catalyzed reduction of azides with diboron under mild conditions

Chen, Yang,Deng, Shengqi,Gao, Yihua,Liu, Liwen,Liu, Yu,Lu, Da,Wang, Qianwen,Zhang, Xiao

supporting information, (2020/02/27)

We report herein the first Cu catalyzed reduction of azides with B2pin2 (pin = pinacolato) as the reductant under very mild conditions. A series of primary amines and amides were obtained in moderate to excellent yields with high chemoselectivity and good functional group tolerance. This reaction can be performed with a cheap copper salt, a simple NHC ligand and a diboron reagent.

Process route upstream and downstream products

Process route

acetic anhydride
108-24-7

acetic anhydride

anilinium nitrate
542-15-4

anilinium nitrate

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

3-nitro-aniline
99-09-2

3-nitro-aniline

Conditions
Conditions Yield
at 0 ℃; Product distribution;
acetic anhydride
108-24-7

acetic anhydride

aniline
62-53-3

aniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

N-nitroaniline
645-55-6

N-nitroaniline

Conditions
Conditions Yield
beim Behandeln von Anilin-nitrat;
1-picryl-pyridinium; nitrate

1-picryl-pyridinium; nitrate

aniline
62-53-3

aniline

trinitro-2,4,6 diphenylamine
2919-12-2

trinitro-2,4,6 diphenylamine

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
nitro acetate
591-09-3

nitro acetate

Acetanilid
103-84-4

Acetanilid

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

3-nitro-aniline
99-09-2

3-nitro-aniline

Conditions
Conditions Yield
at -20 - -10 ℃;
N-nitroaniline
645-55-6

N-nitroaniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
bei laengerem Liegen am Licht;
N-nitroaniline
645-55-6

N-nitroaniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

2-hydroxynitrobenzene
88-75-5,78813-12-4

2-hydroxynitrobenzene

Conditions
Conditions Yield
at 97 - 98 ℃; vorsichtigem Erhitzen; weiter Produkte: Nitrosobenzol, salpetrige Saeure, Kohlendioxid und Stickstoff;
o-nitroacetanilide
552-32-9

o-nitroacetanilide

picramide
489-98-5

picramide

2,4-dinitroacetanilide
610-53-7

2,4-dinitroacetanilide

2-nitro-aniline
88-74-4

2-nitro-aniline

2,4-Dinitroanilin
97-02-9

2,4-Dinitroanilin

Conditions
Conditions Yield
With sodium nitrate; sulfuric acid; for 3h; Ambient temperature;
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h; Product distribution; Mechanism; other sulfenamide reagents, other nitroarenes;
71%
14%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
14%
71%
With potassium tert-butylate; N,N-tetramethylene-thiocarbamoyl-sulphenamide; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
14%
71%
With 2,4,6-trichlorosulfenamide; potassium tert-butylate; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
35%
34%
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride; In N,N-dimethyl-formamide; Product distribution; Ambient temperature; copper-catalyzed amination of nitrobenzenes with O-alkylhydroxylamines; regioselectivity; effect of substituents in aromatic ring on orientation of amination; possible reaction mechanism;
With O-Methylhydroxylamin; potassium tert-butylate; copper(l) chloride; In N,N-dimethyl-formamide; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
With potassium tert-butylate; N,N,N-trimethylhydrazinium iodide; In dimethyl sulfoxide; Yield given. Yields of byproduct given; Ambient temperature;
With O-ethylhydroxylamine hydrochloride; copper(l) chloride; In N,N-dimethyl-formamide; at 20 ℃; for 1h; Further Variations:; Reagents; also without CuCl; other time; Product distribution;
aniline
62-53-3

aniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
With nickel ammonium sulfate; nitric acid; In chloroform; water; at 20 ℃; for 4h;
88%
12%
With potassium hydrogensulfate; potassium metaperiodate; silica gel; sodium nitrite; In neat (no solvent); for 0.0833333h; Reagent/catalyst; Solvent; Microwave irradiation;
86%
With Iron(III) nitrate nonahydrate; at 84.84 ℃; for 0.25h; regioselective reaction;
77%
23%
With bromine; silver nitrate; triphenylphosphine; In acetonitrile; at 20 ℃; for 0.0833333h;
61%
30%
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one; In acetic acid; for 3h; Ambient temperature;
30%
50%
With nitric acid; for 0.166667h; Overall yield = 42 %;
With sodium nitrite; for 0.0333333h; Reagent/catalyst; Microwave irradiation;
With potassium hydrogensulfate; sodium perborate hexahydrate; sodium nitrite; In acetonitrile; at 60 ℃; regioselective reaction;
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

diethyl ether
60-29-7,927820-24-4

diethyl ether

N-nitroaniline
645-55-6

N-nitroaniline

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

2-nitro-aniline
88-74-4

2-nitro-aniline

Conditions
Conditions Yield
at 0 ℃;

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