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4-Nitrophenol

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4-Nitrophenol Basic information

Product Name:
4-Nitrophenol
Synonyms:
  • 1-Hydroxy-4-nitrobenzene
  • 4-hydroxy-1-nitrobenzene
  • 4-Nitrofenol
  • 4-nitro-pheno
  • PARA-NITROPHENOL
  • P-NITROPHENOL
  • HONP
  • ACETAMINOPHEN IMPURITY F
CAS:
100-02-7
MF:
C6H5NO3
MW:
139.11
EINECS:
202-811-7
Product Categories:
  • Aromatics
  • Analytical Chemistry
  • Biochemistry
  • Coupling Reactions (Peptide Synthesis)
  • Indicator (pH)
  • Peptide Synthesis
  • Organics
  • Phenoles and thiophenoles
  • pH Indicators
  • dye intermediates, pharmaceutical and pesticide
  • Nitro
Mol File:
100-02-7.mol
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4-Nitrophenol Chemical Properties

Melting point:
112 °C
Boiling point:
279 °C(lit.)
Density 
1,27 g/cm3
vapor pressure 
0.6 mm Hg ( 120 °C)
refractive index 
1.5723 (estimate)
Flash point:
169 °C
storage temp. 
2-8°C
solubility 
ethanol: soluble95%, clear, dark yellow (100 mg/mL)
form 
Crystalline Powder, Crystals and/or Chunks
pka
7.15(at 25℃)
color 
Yellow to brown
Specific Gravity
1.479
Odor
Odorless
PH
4.4 (5g/l, H2O, 24℃)(anhydrous substance)
PH Range
5.3(colorless)-7.6(Yellow)
Water Solubility 
1.6 g/100 mL (25 ºC)
λmax
320nm, 405nm
Sensitive 
Light Sensitive
Merck 
14,6620
BRN 
1281877
Henry's Law Constant
1.63 x 10-7 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997)
Stability:
Stable. Incompatible with strong oxidizing agents, strong bases, organics, combustible material, reducing agents. Combustible.
Major Application
Display device, solar cells, nanoparticles, electrolytic capacitors, lithographic printing plate, leak detection method, falsification-proof security paper, correction fluid, detergent, fertilizer, identifying fresh and stale rice, diapers, detecting lactic acid bacteria, drug delivery, evaluating dental caries activity
CAS DataBase Reference
100-02-7(CAS DataBase Reference)
NIST Chemistry Reference
Phenol, 4-nitro-(100-02-7)
EPA Substance Registry System
p-Nitrophenol (100-02-7)
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Safety Information

Hazard Codes 
Xn,T,F
Risk Statements 
20/21/22-33-39/23/24/25-23/24/25-11
Safety Statements 
28-28A-45-36/37-16-7
RIDADR 
UN 1663 6.1/PG 3
WGK Germany 
2
RTECS 
SM2275000
8
Autoignition Temperature
541 °F
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
III
HS Code 
29089000
Hazardous Substances Data
100-02-7(Hazardous Substances Data)
Toxicity
LD50 orally in mice, rats: 467, 616 mg/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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4-Nitrophenol Usage And Synthesis

Description

4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. Generally, 4-nitrophenol is used in manufacturing of drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes, and to darken leather.

Chemical Properties

Yellow to tan crystals or powder

Uses

Used in the manufacturing of pharmaceuticals, fungicides, dyes.

Uses

manufacture of pharmaceuticals, fungicides, dyes. Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow.

Uses

4-Nitrophenol is used in dyestuff and pesticide synthesis, as a fungicide, bactericide, and wood preservative, as a chemical indicator, and as a substrate for experiments on cytochrome P450 2E1.

Definition

ChEBI: A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 1607, 1986 DOI: 10.1016/S0040-4039(00)84326-9

General Description

A white to light yellow crystalline solid. Contact may severely irritate skin and eyes. Poisonous by ingestion and moderately toxic by skin contact.

Air & Water Reactions

Soluble in hot water and more dense than water.

Reactivity Profile

4-Nitrophenol is a slightly yellow, crystalline material, moderately toxic. Mixtures with diethyl phosphite may explode when heated. Decomposes exothermally, emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Decomposes violently at 279°C and will burn even in absence of air [USCG, 1999]. Solid mixtures of the nitrophenol and potassium hydroxide (1:1.5 mol) readily deflagrate [Bretherick, 5th Ed., 1995].

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 or skin causes irritation; can be absorbed through skin to give same symptoms as for inhalation.

Safety Profile

Poison by ingestion, subcutaneous, intraperitoneal, intravenous, and intramuscular routes. Moderately toxic by skin contact. Human mutation data reported. Its exothermic decomposition causes a dangerously fast pressure increase. Murtures with diethyl phosphite may explode when heated. When heated to decomposition it emits toxic fumes of NOx. See also other nitrophenol entries and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Environmental Fate

Biological. Under anaerobic conditions, 4-nitrophenol may undergo nitroreduction producing 4- aminophenol (Kobayashi and Rittman, 1982). Estuarine sediment samples collected from the Mississippi River near Leeville, LA were used to study the mineralization of 4-nitrophenol under aerobic and anaerobic conditions. The rate of mineralization to carbon dioxide was found to be faster under aerobic conditions (1.04 x 10-3 μg/day/g dry sediment) than under anaerobic conditions (2.95 x 10-5 μg/day/g dry sediment) (Siragusa and DeLaune, 1986). In lake water samples collected from Beebe and Cayuga Lakes, Ithaca, NY, 4-nitrophenol at 50, 75, and 100 μg/L was not mineralized after 7 d. When the lake water samples were inoculated with the microorganism Corynebacterium sp., extensive mineralization was observed. However, at a concentration of 26 μg/L the extent of mineralization was much lower than at higher concentrations. The presence of a eucaryotic inhibitor (cycloheximide) also inhibited mineralization at the lower concentration but did not affect mineralization at the higher concentrations (Zaidi et al., 1989).
Surface Water. Photodegration half-lives of 5.7, 6.7, and 13.7 d were reported at pH values of 5, 7, and 9, respectively (Hustert et al., 1981).
Groundwater. Nielsen et al. (1996) studied the degradation of 4-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 4-nitrophenol concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life were 0.2/d and 3.47 d, respectively.
Photolytic. An aqueous solution containing 200 ppm 4-nitrophenol exposed to sunlight for 1–2 months yielded hydroquinone, 4-nitrocatechol, and an unidentified polymeric substance (Callahan et al., 1979). Under artificial sunlight, river water containing 2 to 5 ppm 4-nitrophenol photodegraded to produce trace amounts of 4-aminophenol (Mansour et al., 1989). A carbon dioxide yield of 39.5% was achieved when 4-nitrophenol adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. Wet oxidation of 4-nitrophenol at 320 °C yielded formic and acetic acids (Randall and Knopp, 1980). Wet oxidation of 4-nitrophenol at an elevated pressure and temperature gave the following products: acetone, acetaldehyde, formic, acetic, maleic, oxalic, and succinic acids (Keen and Baillod, 1985).

Metabolic pathway

4-[U-14C]Nitrophenol is conjugated as its b-glucoside (ca 22% of applied 14C) and gentiobioside, glc- b(126)-glc-b-4-nitrophenol (ca 64%), while about 7% of the parent remains unchanged in cell suspension cultures of Datura stramonium (L.). Gal-b-4-nitrophenol is found to be a minor metabolite.

Purification Methods

Crystallise 4-nitrophenol from water (which may be acidified, e.g. with N H2SO4 or 0.5N HCl), EtOH, aqueous MeOH, CHCl3, *benzene or pet ether, then dry it in vacuo over P2O5 at 25o. It can be sublimed at 60o/10-4mm. The 4-nitrobenzoate had m 159o (from EtOH). [Beilstein 6 IV 1279.]

Toxicity evaluation

The major hazards has been encountered in the use and handling of 4-nitrophenolstem from its toxicologic properties. 4-Nitrophenol irritates the eyes, skin, and respiratory tract. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methemoglobin which is responsible for methemoglobinemia, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response.

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