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CAS No.: | 88-75-5 |
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Name: | 2-Nitrophenol |
Article Data: | 527 |
Molecular Structure: | |
Formula: | C6H5NO3 |
Molecular Weight: | 139.111 |
Synonyms: | Phenol,o-nitro- (8CI);2-Hydroxynitrobenzene;NSC 1552;o-Hydroxynitrobenzene;o-Nitrophenol;CCRIS 2314;CHEBI:16260;NSC 1552;Ortho-nitrophenol; |
EINECS: | 201-857-5 |
Density: | 1.395 g/cm3 |
Melting Point: | 43-47 °C |
Boiling Point: | 215.8 °C at 760 mmHg |
Flash Point: | 97.1 °C |
Solubility: | 2 g/L (25 °C) in water |
Appearance: | yellow crystalline solid |
Hazard Symbols: | Xn, T, F |
Risk Codes: | 22-36/37/38-52/53-33-20/21/22-39/23/24/25-23/24/25-11 |
Safety: | 26-61-45-36/37-16-7-36-28 |
Transport Information: | UN 1663 6.1/PG 3 |
PSA: | 66.05000 |
LogP: | 1.82360 |
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating; | A 100% B 98% |
methoxy-(2-nitro-phenoxy)-methane
2-hydroxynitrobenzene
Conditions | Yield |
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sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1h; | 100% |
With Montmorillonite K 10 In benzene at 25℃; for 5h; | 93% |
Conditions | Yield |
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With pentamethylbenzene,; boron trichloride In dichloromethane at -78℃; for 0.333333h; | 100% |
With methyl-phenyl-thioether; trifluoroacetic acid In toluene at 20℃; for 3h; | 97% |
With thiophene; sodium hydrogen sulfate; silica gel for 4.5h; Heating; | 94% |
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere; | 78% |
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃; |
Conditions | Yield |
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With [CuII2(μ-OH)(1,2-bis(2-(bis(2-pyridylmethyl)aminomethyl)-6-pyridyl)ethane)](ClO4)3 ; dihydrogen peroxide; triethylamine In water; acetonitrile at 50℃; for 40h; Catalytic behavior; Inert atmosphere; | 99% |
bei der Einw. von Radiumstrahlen; | |
With H5PV2Mo10O40(1,11); oxygen at 140℃; under 1500.12 Torr; Kinetics; Further Variations:; Pressures; reagent concentration; |
Conditions | Yield |
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With 1-methyl-2-pyridone; dinitrogen tetroxide; Nitrogen dioxide In acetonitrile | 98% |
With nitric acid In 1,2-dichloro-ethane at 25℃; for 3h; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent; Temperature; Time; regioselective reaction; | 98.3% |
With ammonium cerium(IV) nitrate for 0.0333333h; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With lithium chloride In N,N-dimethyl-formamide for 6h; Heating; | 98% |
With water; hydrogen bromide; Aliquat 336 at 105℃; for 4.5h; Catalytic behavior; | 92% |
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave; | 87% |
With pyridine hydrochloride for 0.266667h; demethylation; microwave irradiation; | 65% |
tert-butyldimethyl(2-nitrophenoxy)silane
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 1.5h; Inert atmosphere; | 98% |
sulfated SnO2 In methanol at 20℃; for 0.166667h; | 96% |
With potassium-exchanged zirconium hydrogen phosphate In water; acetone at 60℃; for 3.5h; desilylation; | 76% |
Conditions | Yield |
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With copper In 1-methyl-pyrrolidin-2-one at 250℃; for 0.5h; | 98% |
benzenesulfonic acid-(2-nitro-phenyl ester)
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere; | 97% |
2-allyloxy-1-nitrobenzene
2-hydroxynitrobenzene
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 8h; | 96% |
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide; mineral oil at 10℃; for 8h; Inert atmosphere; | 92% |
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 20℃; for 4h; Inert atmosphere; | 72% |
The 2-Nitrophenol with CAS registry number of 88-75-5 is also known as Phenol, 2-nitro-. The IUPAC name and product name are the same. It belongs to product categories of Intermediates of Dyes and Pigments; Organics; Phenoles and thiophenoles; Analytical Chemistry; Indicator (pH); pH Indicators; Indicators; PH Indicators - Solids; Titration; Organic Building Blocks; Oxygen Compounds; Phenols; Alpha Sort; N; NA - NI; N-OAlphabetic; Volatiles/ Semivolatiles; N-PAlphabetic; Pesticides&Metabolites; Dye Intermediates. Its EINECS registry number is 201-857-5. In addition, the formula is C6H5NO3 and the molecular weight is 139.11.
Physical properties about 2-Nitrophenol are: (1)ACD/LogP: 1.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.7; (4)ACD/LogD (pH 7.4): 1.26; (5)ACD/BCF (pH 5.5): 11.45; (6)ACD/BCF (pH 7.4): 4.15; (7)ACD/KOC (pH 5.5): 198.06; (8)ACD/KOC (pH 7.4): 71.84; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.612; (13)Molar Refractivity: 34.67 cm3; (14)Molar Volume: 99.7 cm3; (15)Surface Tension: 60.2 dyne/cm; (16)Density: 1.395 g/cm3; (17)Flash Point: 97.1 °C; (18)Enthalpy of Vaporization: 47.06 kJ/mol; (19)Boiling Point: 215.8 °C at 760 mmHg; (20)Vapour Pressure: 0.0987 mmHg at 25 °C.
Preparation of 2-Nitrophenol: it is prepared by reaction of nitrochlorobenzene with sodium hydroxide and sulfuric acid. The reaction has two steps of hydrolysis and acidification.
Uses of 2-Nitrophenol: it is used to produce 3-(2-nitro-phenoxy)-propionic acid by reaction with oxetan-2-one. The reaction occurs with reagent NaOH and other condition of heating for 40 minutes. The yield is about 37%. This chemical is used as organic synthesis intermediate of medicine, dyes, rubber chemicals, photographic materials and also can be used as color pH indicator.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. It's harmful and has danger of very serious irreversible effects by inhalation, in contact with skin and if swallowed. Besides, it is highly flammable and harmful to aquatic organisms that may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing, gloves and eye/face protection. Keep away from sources of ignition and avoid release to the environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If accident happens or you feel unwell seek medical advice immediately. After using it, keep container tightly closed. After contact with skin, wash immediately.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC=C(C(=C1)[N+](=O)[O-])O
2. InChI: InChI=1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H
3. InChIKey: IQUPABOKLQSFBK-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | subcutaneous | 600mg/kg (600mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 120, 1959. | |
dog | LD50 | intravenous | 100mg/kg (100mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 675, 1986. | |
frog | LDLo | subcutaneous | 300mg/kg (300mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 120, 1959. | |
guinea pig | LDLo | subcutaneous | 900mg/kg (900mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA | Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896. |
mouse | LD50 | intraperitoneal | 378mg/kg (378mg/kg) | Journal of Medicinal Chemistry. Vol. 18, Pg. 868, 1975. | |
mouse | LD50 | oral | 1297mg/kg (1297mg/kg) | Aerospace Medical Research Laboratory Report. Vol. TR-72-62, Pg. 1972, | |
mouse | LDLo | intramuscular | 600mg/kg (600mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 120, 1959. | |
rabbit | LD50 | skin | > 7940mg/kg (7940mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 74, 1990. |
rabbit | LDLo | subcutaneous | 1700mg/kg (1700mg/kg) | "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 120, 1959. | |
rat | LD50 | intraperitoneal | 840mg/kg (840mg/kg) | BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA KIDNEY, URETER, AND BLADDER: STRUCTURAL OR FUNCTIONAL CHANGES IN URETER | National Technical Information Service. Vol. OTS0545982, |
rat | LD50 | oral | 334mg/kg (334mg/kg) | Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972. | |
rat | LDLo | subcutaneous | 1100mg/kg (1100mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA | Revue Medicale de la Suisse Romande. Vol. 16, Pg. 449, 1896. |