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)

pka

7.15(at 25℃)

form 

Crystalline Powder, Crystals and/or Chunks

color 

Yellow to brown

Specific Gravity

1.479

Odor

Odorless

PH Range

5.3(colorless)-7.6(Yellow)

PH

4.4 (5g/l, H2O, 24℃)(anhydrous substance)

Water Solubility 

1.6 g/100 mL (25 ºC)

Sensitive 

Light Sensitive

λmax

320nm, 405nm

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)

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

F 

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 (mixed α- and β-forms), The (metastable) α-form crystallizes from toluene above 63°C, and the yellow, prismatic β-form crystallizes from toluene below 63°C. 4-Nitrophenol is not steam volatile and is much more soluble in water (30 % at 100°C) than the ortho isomer.

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.
4-Nitrophenol is used as a precursor to prepare phenetidine, acetophenetidne and pH indicator. Its carboxylate ester derivatives are involved as an active component for the construction of amide moieties in peptide synthesis. It is used as an intermediate in the synthesis of paracetamol and N-acetyl-p-aminophenol dyestuffs.

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.

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.

Synthesis Reference(s)

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

General Description

4-nitrophenol appears as 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

Acute inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis. Contact with the eyes causes irritation.
A study examining the acute effects of 4-nitrophenol from inhalation exposure in rats reported an increase in methemoglobin and corneal opacity.
Tests involving acute exposure of rats and mice have shown 4-nitrophenol to have high toxicity from oral and dermal exposure.

Flammability and Explosibility

Non flammable

Safety Profile

4-Nitrophenol is used to manufacture drugs, fungicides, insecticides, and dyes and to darken leather. Acute (short-term) inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis (blue color in lips, ears, and fingernails). Contact with eyes causes irritation in humans. No information is available on the chronic (long-term) effects of 4-nitrophenol in humans or animals from inhalation or oral exposure. No information is available on the reproductive, developmental, or carcinogenic effects of 4-nitrophenol in humans. EPA has not classified 4-nitrophenol for potential carcinogenicity.

Synthesis

4-Nitrophenol is synthesized by Nitration of para-Toluenesulfonic ester of Phenol, followed by hydrolysis is obtained a fairly pure material.

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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