| Identification | More | [Name]
4-Nitrophenol | [CAS]
100-02-7 | [Synonyms]
4-HYDROXYNITROBENZENE
4-NITROHYDROXYBENZENE
ACETAMINOPHENE IMP F
ACETAMINOPHEN IMPURITY F
AKOS BBS-00004351
HONP
PARA-NITROPHENOL
P-NITROPHENOL
1-Hydroxy-4-nitrobenzene
4-hydroxy-1-nitrobenzene
4-Nitrofenol
4-nitro-pheno
Mononitrophenol
NCI-C55992
Niphen
Paranitrofenol
Paranitrofenolo
Phenol, p-nitro-
Phenol,4-nitro-
p-Hydroxynitrobenzene | [EINECS(EC#)]
202-811-7 | [Molecular Formula]
C6H5NO3 | [MDL Number]
MFCD00007331 | [Molecular Weight]
139.11 | [MOL File]
100-02-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Yellow to tan crystals or powder | [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) | [Fp ]
169 °C
| [storage temp. ]
Store in dark! | [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) | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong bases, organics, combustible material, reducing agents. Combustible. | [Water Solubility ]
1.6 g/100 mL (25 ºC) | [Sensitive ]
Light Sensitive | [λmax]
320nm, 405nm | [Merck ]
14,6621 | [BRN ]
1281877 | [Henry's Law Constant]
1.63 x 10-7 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) | [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]
100-02-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T,F | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R33:Danger of cumulative effects.
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 1663 6.1/PG 3
| [WGK Germany ]
2
| [RTECS ]
SM2275000
| [F ]
8 | [Autoignition Temperature]
541 °F | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29089000 | [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. | [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) |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
4-NITROPHENOL(100-02-7) 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]. | [Air & Water Reactions]
Soluble in hot water and more dense than water. | [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. | [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]
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. | [Uses]
manufacture of pharmaceuticals, fungicides, dyes. Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow. | [Uses]
Used in the manufacturing of pharmaceuticals, fungicides, dyes. | [Application]
4-Nitrophenol (4-NP) is used to manufacture pharmaceuticals, fungicides, insecticides, and dyes and to darken leather. Indicator in 0.1% alcohol solution. pH: 5.6 colorless, 7.6 yellow. It can be used to prepare 4-aminophenol (4-AP), a key intermediate for the manufacture of analgesic and antipyretic drugs. | [Definition]
ChEBI: 4-nitrophenol is 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. It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate acid of a 4-nitrophenolate. | [Preparation]
4-Nitrophenol was synthesized from p-nitrochlorobenzene by hydrolysis and acidification. Add 2320-2370L of sodium hydroxide solution with a concentration of 137-140g/L to the hydrolysis pot, and then add 600kg of molten p-nitrochlorobenzene. Heat to 152℃, pressure in the pot is 0.4MPa, then stop heating, the hydrolysis reaction exotherm makes the temperature and pressure rise naturally to 165℃, about 0.6MPa. keep 3h and take sample to check the end point of the reaction, after the reaction is finished, the hydrolysate is cooled to 120℃. Add 600L water and 50L concentrated sulfuric acid to the crystallization pot, press into the above hydrolysis and cool to about 50℃, add concentrated sulfuric acid to make the Congo red test paper purple, continue to cool to 30℃, filter, centrifuge to shake off the water, get more than 90% of 4-nitrophenol about 500kg, 92% yield. | [Synthesis Reference(s)]
Tetrahedron Letters, 27, p. 1607, 1986 DOI: 10.1016/S0040-4039(00)84326-9 | [Flammability and Explosibility]
Nonflammable | [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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