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2-Nitrophenol

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2-Nitrophenol Basic information

Product Name:
2-Nitrophenol
CAS:
88-75-5
MF:
C6H5NO3
MW:
139.11
EINECS:
201-857-5
Mol File:
88-75-5.mol
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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
Flash point:
108 °C
storage temp. 
Store in dark!
solubility 
2 g/L (25°C)
form 
Liquid
pka
7.17(at 25℃)
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
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)
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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 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29089000
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)

MSDS

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2-Nitrophenol Usage And Synthesis

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 a chemical indicator.

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

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-nitrophenol to nitrite. Degradation by enzymatic mechanisms produced nitrite and catechol. Catechol subsequently degraded to β-ketoadipic acid (Zeyer and Kearney, 1984). When 2-nitrophenol was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, 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 (organic matter-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 the formation 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 microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine 2-nitrophenol concentrations with time. The experimentally determined first-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 for the reaction of 2-nitrophenol and OH radicals in the atmosphere (Atkinson, 1985). Chemical/Physical. Oxidation by Fenton’s reagent (hydrogen peroxide and Fe3+) produced nitrohydroquinone and 3-nitrocatechol (Andersson et al., 1986). In an aqueous solution (initial pH 5.0), 2-nitrophenol (100 μM) reacted with Fenton’s reagent (35 μM). After 60-min and 4-h, about 50 and 90% of the 2-nitrophenol was destroyed, respectively. The pH of the solution decreased due 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.]

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