2-Nitrophenol CAS 88-75-5
Introduction：Basic information about 2-Nitrophenol CAS 88-75-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Nitrophenol Basic information
| Product Name: | 2-Nitrophenol |
| Synonyms: | 2-HYDROXYNITROBENZENE;2-NITROPHENOL;2-Nitrophenol (0.1% in Water) [for pH Determination];2-hydroxynitrobenzene[qr];O-NITROPHENOL;2-Nitrophenol o-Nitrophenol;2-NITROPHENOL, 5000MG, NEAT;2-NITROPHENOL, 1X1ML, MEOH, 5000UG/ML |
| CAS: | 88-75-5 |
| MF: | C6H5NO3 |
| MW: | 139.11 |
| EINECS: | 201-857-5 |
| Product Categories: | Nitro;Pharmaceutical Intermediates;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 |
| Mol File: | 88-75-5.mol |
2-Nitrophenol Chemical Properties
| Melting point | 43-45 °C |
| Boiling point | 214-216 °C |
| density | 1.495 |
| vapor pressure | 1 mm Hg ( 49.3 °C) |
| refractive index | 1.5723 |
| Fp | 108 °C |
| storage temp. | Store in dark! |
| solubility | 2 g/L (25°C) |
| pka | 7.17(at 25℃) |
| form | Liquid |
| color | Clear pale yellow |
| Odor | Aromatic odor |
| PH | 5.0～7.0 |
| PH Range | Colorless (5.0) to yellow (7.0) |
| Water Solubility | 2 g/L (25 ºC) |
| Sensitive | Light Sensitive |
| Merck | 14,6619 |
| BRN | 775403 |
| Henry's Law Constant | At 20 °C: 11.1 at pH 8.1, 11.0 at pH 10.2, 8.9 at pH 11.9, 6.7 at pH 13.7 (wetted-wall column-UV,Zhang et al., 2003) |
| Stability: | Stable. Incompatible with strong bases, strong oxidizing agents. |
| Major Application | High voltage capacitors, inks, energetic materials, corrosion inhibitors, fertilizer, food storage, enzyme assays, detecting microorganisms, immunotherapy, drugs |
| Cosmetics Ingredients Functions | HAIR DYEING |
| InChI | 1S/C6H5NO3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H |
| InChIKey | IQUPABOKLQSFBK-UHFFFAOYSA-N |
| SMILES | Oc1ccccc1[N+]([O-])=O |
| LogP | 1.77 |
| Dissociation constant | 7.23 at 25℃ |
| CAS DataBase Reference | 88-75-5(CAS DataBase Reference) |
| NIST Chemistry Reference | Phenol, 2-nitro-(88-75-5) |
| EPA Substance Registry System | o-Nitrophenol (88-75-5) |
Safety Information
| Hazard Codes | Xn,T,F |
| Risk Statements | 22-36/37/38-52/53-33-20/21/22-39/23/24/25-23/24/25-11 |
| Safety Statements | 26-61-45-36/37-16-7-36-28 |
| RIDADR | UN 1663 6.1/PG 3 |
| WGK Germany | 2 |
| RTECS | SM2100000 |
| Autoignition Temperature | 550 °C |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29089000 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 88-75-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice, rats: 1.297, 2.828 g/kg, K. C. Back et al., Reclassification of Materials Listed as Transportation Health Hazards (TSA-20-72-3; PB214-270, 1972) |
| Chemical Properties | yellow crystalline solid |
| Uses | manufacture of dyes, paint colorings, rubber chemicals, and fungicides. Indicator in 2% alcohol solution. pH: 5.0 colorless, 7.0 yellow, but the color change is not sharp and cannot be used where CO2 is present; as reagent for glucose. |
| Uses | 2-Nitrophenol is an intermediate in dyestuff production and achemical indicator. |
| Uses | 2-Nitrophenol is a building block used as an acid-base indicator and corrosion inhibitor for aluminum-copper alloy. It is also used to make dyes, paint coloring, rubber chemicals, and substances that kill molds. |
| Production Methods | 2-Chloronitrobenzene in 8.5 % sodium hydroxide solution is heated gradually (exothermic) to 170 ℃ in an autoclave and held there under pressure for 8 h. The resulting solution is cooled and acidified to give the product 2-Nitrophenol in 95 % yield. |
| Definition | ChEBI: A member of the class of 2-nitrophenols that is phenol in which one of the hydrogens that is ortho to the hydroxy group has been replaced by a nitro group. |
| Synthesis Reference(s) | Canadian Journal of Chemistry, 67, p. 220, 1989 DOI: 10.1139/v89-037 Tetrahedron, 44, p. 4555, 1988 DOI: 10.1016/S0040-4020(01)86158-5 |
| General Description | Yellow solid. Sinks in and mixes slowly with water. |
| Air & Water Reactions | Water insoluble. |
| Reactivity Profile | 2-Nitrophenol is a yellow, crystalline material, moderately toxic, low melting point (45° C). When heated to decomposition 2-Nitrophenol emits toxic fumes of oxides of nitrogen. In molten form violent reaction with strong alkali (85 % potassium hydroxide) [491 M, 1975, p. 342]. Reaction product with chlorosulfuric acid decomposes violently at room temperature [Vervalin, C. H., Hydrocarbon Proc., 1976, 55(9), p. 321]. |
| Hazard | Toxic by ingestion. |
| Health Hazard | Inhalation or ingestion causes headache, drowsiness, nausea, and blue color in lips, ears, and fingernails (cyanosis). Contact with eyes causes irritation. Can be absorbed through the intact skin to give same symptoms as for inhalation. |
| Fire Hazard | Special Hazards of Combustion Products: Toxic and irritating fumes of unburned material and oxides of nitrogen can form in fire. |
| Environmental fate | Biological. A microorganism, Pseudomonas putida, isolated from soil degraded 2-nitrophenolto nitrite. Degradation by enzymatic mechanisms produced nitrite and catechol. Catecholsubsequently degraded to β-ketoadipic acid (Zeyer and Kearney, 1984). When 2-nitrophenol wasstatically incubated in the dark at 25 °C with yeast extract and settled domestic wastewaterinoculum, 100% biodegradation with rapid adaptation was achieved after 7 d (Tabak et al., 1981).In a similar study, 2-nitrophenol degraded rapidly from flooded alluvial and pokkali (organicmatter-rich acid sulfate) soils that were inoculated with parathion-enrichment culture containing 5-day-old cultures of Flavobacterium sp. ATCC 27551 and Pseudomonas sp. ATCC 29353(Sudhaker-Barik and Sethunathan, 1978a). 2-Nitrophenol disappeared completely with theformation of nitrite, particularly in the inoculated soils rather than in the uninoculated soils. Groundwater. Nielsen et al. (1996) studied the degradation of 2-nitrophenol in a shallow,glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosmstudy, a cylinder that was open at the bottom and screened at the top was installed through a casedborehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air toensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately3 months to determine 2-nitrophenol concentrations with time. The experimentally determinedfirst-order biodegradation rate constant and corresponding half-life were 0.05/d and 13.86 d,respectively. Photolytic. A second-order reaction rate constant of 9 x 10-13 cm3/molecule?sec was reported forthe reaction of 2-nitrophenol and OH radicals in the atmosphere (Atkinson, 1985).Chemical/Physical. Oxidation by Fenton’s reagent (hydrogen peroxide and Fe3+) producednitrohydroquinone and 3-nitrocatechol (Andersson et al., 1986). In an aqueous solution (initial pH5.0), 2-nitrophenol (100 μM) reacted with Fenton’s reagent (35 μM). After 60-min and 4-h, about50 and 90% of the 2-nitrophenol was destroyed, respectively. The pH of the solution decreaseddue to the formation of nitric acid (Lipczynska-Kochany, 1991). |
| Purification Methods | Crystallise 2-nitrophenol from EtOH/water, water, EtOH, *benzene or MeOH/pet ether (b 70-90o). It can be steam distilled. Petrucci and Weygandt [Anal Chem 33 275 1961] crystallised it from hot water (twice), then EtOH (twice), followed by fractional crystallisation from the melt (twice), drying over CaCl2 in a vacuum desiccator and then in a drying pistol. The 4-nitrobenzoate had m 141o (from EtOH). [Beilstein 6 IV 1246.] |
| Toxics Screening Level | The acute Initial Threshold Screening Level (ITSL) for 2-nitrophenol is 18 μg/m3 with 24-hr averaging time. |
2-Nitrophenol Preparation Products And Raw materials
| Raw materials | Sodium hydroxide-->Sulfuric acid-->2-Nitrochlorobenzene-->Congo red paper-->4-Nitrophenol |
| Preparation Products | o-Anisidine-->Carbofuran-->2-Aminophenol-->C-(3,4-DIHYDRO-2H-BENZO[1,4]OXAZIN-3-YL)-METHYLAMINE-->BAPTA, TETRASODIUM SALT-->BAPTA-->2,3-Dihydro-2,2-dimethyl-7-benzofuranol-->8-Hydroxyquinoline-->5-Methoxymethyl-2,3-pyridinedicarboxylic acid-->2-Amino-6-bromophenol-->2-Aminophenol-4-sulfonic acid-->2-Nitrophenoxyacetic acid-->2-(2-MORPHOLIN-4-YLETHOXY)ANILINE-->8-Hydroxyquinaldine-->2,6-DINITROPHENOL-->2-NITROTHIOPHENOL-->3-Nitrosalicylic acid |
