3-Nitrophenol Chemical Properties

Melting point:

96-98 °C (lit.)

Boiling point:

194 °C/70 mmHg (lit.)

Density 

1,49 g/cm³

refractive index 

1.5723 (estimate)

Flash point:

102°C

storage temp. 

Store at +5°C to +30°C.

solubility 

13.5g/l insoluble

form 

Crystalline Powder

pka

8.28(at 25℃)

color 

Yellow to brown

PH

6.6-8.6 (H2O, 20℃)

PH Range

6.6(colourless)-8.6(yellow/orange)

Water Solubility 

13.5 g/L (25 ºC)

λmax

570nm

Merck 

14,6618

BRN 

1907946

Major Application

Display device, semiconductor device, sensors, high voltage capacitors, energetic materials, electrolyte batteries, inks, correction fluid, detergent, leak detection method, lubricants, insecticide, food storage, inhibition of amyloidoses, detect bacterialinfection, drugs, material for evaluating dental caries activity

InChIKey

RTZZCYNQPHTPPL-UHFFFAOYSA-N

CAS DataBase Reference

554-84-7(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 3-nitro-(554-84-7)

EPA Substance Registry System

m-Nitrophenol (554-84-7)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-38-41-36/37/38-33-20/21/22

Safety Statements 

26-36/37-45-36/37/39-22-28

RIDADR 

UN 1663 6.1/PG 3

WGK Germany 

3

RTECS 

SM1925000

F 

8

Autoignition Temperature

400 °C

Hazard Note 

Harmful/Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29089000

Hazardous Substances Data

554-84-7(Hazardous Substances Data)

Toxicity

LD50 orally in mice, rats: 1414, 933 mg/kg, K. C. Back et al., Reclassification of Materials Listed as Transportation Health Hazards (TSA-20-72-3; PB214-270, 1972)

MSDS

• Language:English Provider:3-Hydroxy-1-nitrobenzene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Nitrophenol Usage And Synthesis

Chemical Properties

yellow to brown crystalline powder

Uses

3-Nitrophenol is a chemical reagent used in various organic syntheses. Used in the synthesis of RAGE inhibitors via the etherification of phenols. Also used in the synthesis of kinase inhibitors against epidermal growth factor receptor T790M mutation.

Uses

As indicator in 0.3% solution in 50% alcohol. pH: 6.8 colorless, 8.6 yellow.

Production Methods

3-Nitroaniline is diazotized in aqueous sulfuric acid and then hydrolyzed by being added gradually to boiling dilute sulfuric acid. The crude product solidifies on cooling and is filtered off in 90 % yield.

Definition

ChEBI: A member of the class of 3-nitrophenols that is phenol in which one of the hydrogens that is meta to the hydroxy group has been replaced by a nitro group.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 5117, 1995 DOI: 10.1016/0040-4039(95)00963-D

General Description

Colorless to pale yellow crystalline solid. Sinks in and mixes with water.

Air & Water Reactions

Water insoluble.

Reactivity Profile

3-Nitrophenol is a light-yellow, crystalline material, toxic and irritant. When heated to decomposition 3-Nitrophenol emits toxic fumes of oxides of nitrogen [Lewis, 3rd ed., 1993, p. 941]. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.

Hazard

Toxic by ingestion.

Health Hazard

INHALATION: Inhalation or ingestion causes headaches, drowsiness, nausea, and blue color in lips, ears, and finger nails (cyanosis). EYES: Contact with eyes causes irritation. SKIN: Can be absorbed through intact skin to give same symptoms as for inhalation.

Fire Hazard

Special Hazards of Combustion Products: Dangerous toxic fumes of NO x

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic by skin contact. A skin and severe eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also other nitrophenol entries.

Purification Methods

Crystallise 3-nitrophenol from water, CHCl3, CS2, EtOH or pet ether (b 80-100o), and dry it under vacuum over P2O5 at room temperature. It can also be distilled at low pressure. The 4-nitrobenzoate had m 174o (from EtOH). [Beilstein 6 IV 1269.]

3-Nitrophenol(554-84-7)Related Product Information

• CHLOROPHOSPHONAZO III
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