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2-Amino-4-nitrophenol

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Name

2-Amino-4-nitrophenol

EINECS 202-767-9
CAS No. 99-57-0 Density 1.511 g/cm3
PSA 92.07000 LogP 1.98700
Solubility slightly soluble in water Melting Point 140-143 °C(lit.)
Formula C6H6N2O3 Boiling Point 368.1 °C at 760 mmHg
Molecular Weight 156.141 Flash Point 176.4 °C
Transport Information N/A Appearance ochre crystalline powder
Safety 26-45-36/37/39-36 Risk Codes 36/37/38-68-43-40-20/21/22
Molecular Structure Molecular Structure of 99-57-0 (2-Amino-4-nitrophenol) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

Phenol, 2-amino-4-nitro-;3-Amino-4-hydroxynitrobenzene;1-Hydroxy-2-amino-4-nitrobenzene;1-Amino-2-hydroxy-5-nitrobenzene;1-Nitro-3-amino-4-hydroxybenzene;2-Hydroxy-5-nitroaniline;2-Amino-4-nitro-phenolate;2-Amino-4-nitrophenol;2-Hydroxy-5-nitroaniline; 3-Amino-4-hydroxynitrobenzene;p-nitro-o-aminophenol;

Article Data 57

2-Amino-4-nitrophenol Synthetic route

51-28-5

2,4-Dinitrophenol

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With hydrazine hydrate at 90℃; for 18h;98%
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;95%
With hydrazine hydrate In isopropyl alcohol at 110℃; for 0.25h; Catalytic behavior; Sealed tube; chemoselective reaction;94%
1011-73-0

sodium 2,4-dinitrophenoxide

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen at 70℃; under 4500.45 Torr; for 2h; Temperature; Pressure; Time; Autoclave;97.1%
1604034-83-4

C6H7BN2O4

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With iron(III) oxide; oxygen In tetrahydrofuran at 20℃; Irradiation;95%
51-28-5

2,4-Dinitrophenol

A

119-34-6

4-amino-2-nitrophenol

B

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With nickel; hydrazine hydrate In ethanol; 1,2-dichloro-ethane at 50 - 60℃; for 4h;A 7%
B 92%
With hydrogen; iron; acetic acid; palladium dichloride In ethanol at 20 - 25℃; under 258.6 - 2327.2 Torr;A n/a
B 79%
With sodium hydroxide; sodium disulfide
With sodium sulfide; 5-hydroxynaphtho-1,4-quinone; water In methanol; phosphate buffer for 12h; pH=2.5; Reduction;
95-55-6

2-amino-phenol

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With nickel ammonium sulfate; nitric acid In chloroform; water at 20℃; for 3h;92%
Multi-step reaction with 2 steps
2: HNO3+H2SO4 / <0 / beim Kochen des Reaktionsprodukts mit Salzsaeure
View Scheme
With sulfuric acid; nitric acid In chloroform at 8 - 12℃; Solvent; Temperature; Large scale;830 kg
33354-58-4

2-azido-4-nitrophenol

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 2.41667h;78%

1-phenyl-2-(piperidin-1-yl)ethanone O-(2,4-dinitrophenyl)oxime

A

51-28-5

2,4-Dinitrophenol

B

99-57-0

2-hydroxy-5-nitroaniline

C

3649-46-5

2-Phenyl-5,6,7,8-tetrahydro-imidazo<1,2-a>pyridin

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Schlenk technique; Sealed tube; Irradiation;A 33%
B 22%
C 75%
99-56-9

4-Nitrophenylene-1,2-diamine

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With water; sodium hydroxide at 100℃; for 4h;65%
95-55-6

2-amino-phenol

A

603-87-2

2-amino-6-nitrophenol

B

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With sulfuric acid; aminosulfonic acid; nitric acid at 0℃; for 0.5h;A 26%
B 44%
369-36-8

6-fluoro-3-nitroaniline

99-57-0

2-hydroxy-5-nitroaniline

Conditions
ConditionsYield
With sodium hydroxide for 72h; Heating;30%

2-Amino-4-nitrophenol Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 57 ,1993,p. 167.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 57 ,1993,p. 167.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 57 ,1993,p. 167.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

2-Amino-4-nitrophenol Specification

2-Amino-4-nitrophenol(CAS NO.99-57-0), its Synonyms are 1-Amino-2-hydroxy-5-nitrobenzene; 1-Hydroxy-2-amino-4-nitrobenzene; 1-Nitro-3-amino-4-hydroxybenzene; 2-Amino-4-nitrophenol; 2-Hydroxy-5-nitroaniline; 3-Amino-4-hydroxynitrobenzene; 4-Nitro-2-aminophenol; p-Nitro-o-aminophenol; Phenol, 2-amino-4-nitro-. It is orange prisms or yellow powder and no odor, slightly soluble in water.With the Molecular Formula of C6H6N2O32-Amino-4-nitrophenol is used as dyes and pharmaceutical intermediate.

Physical properties about 2-Amino-4-nitrophenol are: (1)ACD/LogP: 1.233; (2)ACD/LogD (pH 5.5): 1.21; (3)ACD/LogD (pH 7.4): 0.53; (4)ACD/BCF (pH 5.5): 4.80; (5)ACD/BCF (pH 7.4): 1.01; (6)ACD/KOC (pH 5.5): 105.13; (7)ACD/KOC (pH 7.4): 22.13; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.689; (12)Molar Refractivity: 38.916 cm3; (13)Molar Volume: 101.985 cm3; (14)Polarizability: 15.428 10-24cm3; (15)Surface Tension: 78.5390014648438 dyne/cm; (16)Density: 1.511 g/cm3; (17)Flash Point: 176.396 °C; (18)Enthalpy of Vaporization: 63.883 kJ/mol; (19)Boiling Point: 368.059 °C at 760 mmHg

When you are using 2-Amino-4-nitrophenol, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
3. Wear suitable protective clothing, gloves and eye/face protection;
4. Wear suitable protective clothing;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H6N2O3/c7-5-3-4(8(10)11)1-2-6(5)9/h1-3,9H,7H2;
(2)InChIKey=VLZVIIYRNMWPSN-UHFFFAOYSA-N;
(3)Smilesc1(cc(c(O)cc1)N)[N+](=O)[O-];

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 143mg/kg (143mg/kg)   Genetica Polonica. Vol. 26, Pg. 109, 1985.
mouse LD50 oral 850mg/kg (850mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981.
rat LD50 intraperitoneal 246mg/kg (246mg/kg)   Journal of Toxicology and Environmental Health. Vol. 2, Pg. 657, 1977.
 
rat LD50 oral 2400mg/kg (2400mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Food and Cosmetics Toxicology. Vol. 15, Pg. 607, 1977.
 

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