4-Nitroanisole Chemical Properties

Melting point:

51-53 °C

Boiling point:

260 °C

Density 

1.233 g/mL at 25 °C(lit.)

refractive index 

1.5030 (estimate)

Flash point:

130 °C

form 

Crystals

Specific Gravity

1.233

color 

Green to brown

Water Solubility 

0.468 g/L (20 ºC)

Merck 

14,6584

BRN 

1865361

Dielectric constant

24.0（20℃）

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

CAS DataBase Reference

100-17-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-methoxy-4-nitro-(100-17-4)

IARC

2B (Vol. 123) 2020

EPA Substance Registry System

p-Nitroanisole (100-17-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

52/53-68

Safety Statements 

61-36/37

RIDADR 

UN 3458 6.1/PG 3

WGK Germany 

1

RTECS 

BZ8800000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29093090

MSDS

• Language:English Provider:1-Methoxy-4-nitrobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Nitroanisole Usage And Synthesis

Chemical Properties

beige crystalline solid. soluble in alcohol, ether and boiling petroleum ether, slightly soluble in cold petroleum ether, insoluble in water.

Uses

o-Isomer as dye intermediate; in organic syntheses.

Uses

4-Nitroanisole is an intermediate in the manufacture of azo dyes. A toxic organic pollutant and a risk factor for urinary bladder cancer in humans.

Definition

ChEBI: 4-nitroanisole is a member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.

Preparation

Produced from p-nitrochlorobenzene by methoxylation.

Synthesis Reference(s)

Synthetic Communications, 25, p. 1367, 1995 DOI: 10.1080/00397919508013838
Tetrahedron Letters, 14, p. 1397, 1973

General Description

A light red or amber-colored liquid or crystals. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation or skin absorption. Used to make other chemicals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Nitroanisole reacts explosively with (sodium hydroxide + zinc). 4-Nitroanisole reacts vigorously with hydrogen + catalyst (at 482° F and 25500 mm Hg).

Health Hazard

Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Biochem/physiol Actions

4-Nitroanisole is O-demethylated to 4-nitrophenol by human liver microsomes.

Safety Profile

A poison by ingestion. Mutation data reported. Can explode in presence of Ni. When heated to decomposition it emits toxic fumes of NOx. See also o-NITROANISOLE and NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.

Purification Methods

Crystallise it from pet ether or hexane and dry it in vacuo. [Beilstein 6 IV 1282.]

4-Nitroanisole(100-17-4)Related Product Information

• 4-Nitrobenzaldehyde
• 3-Nitrobenzaldehyde
• 4-Methyl-3-nitroanisole
• 3,4-Difluoronitrobenzene
• Butylated hydroxyanisole
• 4-NITROPHENYLACETYLENE
• 4-Nitrobenzonitrile
• 4-Fluoronitrobenzene
• Sodium 3-nitrobenzenesulphonate
• 4-Nitrobenzoic acid
• 4-Nitrobenzeneethanol
• 4-Nitrophenyl chloroformate
• 4-Nitrobenzenesulfonyl chloride
• Anisole
• p-Nitrophenylacetonitrile
• 4-Nitrophenylacetic acid
• 4-Nitrotoluene
• 4-Nitroaniline