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4-Nitroanisole

CAS No.
100-17-4
Chemical Name:
4-Nitroanisole
Synonyms
1-METHOXY-4-NITROBENZENE;Nitroanisole;4-Nitroanisol;PARA-NITROANISOLE;4-Nitroanisole,98%;p-Nitroanisol;p-nitro-anisol;4-NITROANISOLE;P-NITROANISOLE;Anisole, p-nitro-
CBNumber:
CB0182966
Molecular Formula:
C7H7NO3
Molecular Weight:
153.14
MDL Number:
MFCD00007327
MOL File:
100-17-4.mol
MSDS File:
SDS
Last updated:2023-11-28 16:31:44

4-Nitroanisole 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
color Green to brown
Specific Gravity 1.233
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)
EWG's Food Scores 1
FDA UNII G989Z7WOLH
Proposition 65 List Para-Nitroanisole
IARC 2B (Vol. 123) 2020
NIST Chemistry Reference Benzene, 1-methoxy-4-nitro-(100-17-4)
EPA Substance Registry System p-Nitroanisole (100-17-4)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Warning
Hazard statements  H351-H412
Precautionary statements  P202-P273-P280-P308+P313-P405-P501
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
NFPA 704
1
1 0

4-Nitroanisole Chemical Properties,Uses,Production

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.]

100-02-7
74-88-4
100-17-4
Synthesis of 4-Nitroanisole from 4-Nitrophenol and Iodomethane
4-METHOXYNITROBENZENE 1-methoxy-4-nitro-benzen 4-Methoxy-1-nitrobenzene 4-Nitrophenyl methyl ether 4-Nitrophenylmethylether Anisole, p-nitro- Benzene,1-methoxy-4-nitro- Methyl p-nitrophenyl ether p-Methoxynitrobenzene p-Nitroanisol p-nitro-anisol p-Nitromethoxybenzene 4-NITROANISOL OEKANAL, 250 MG 4-Nitroanisole, 99+% 4-NITROANISOLE / 4-METHOXYNITROBENZENE 4-Nitro-1-methoxybenzene Methyl(4-nitrophenyl) ether 4-Nitroanisole,1-Methoxy-4-nitrobenzene p-Nitroanisole 1g [100-17-4] 4-Methoxynitrobenzene, 1-Methoxy-4-nitrobenzene 4-Nitroanisole, 99+% 250GR 4-Nitroanisole, 99+% 5GR 4-NITROANISOLE 4-Nitroanisole p-Nitroanisole p-Nitrophenylmethylether P-NITROANISOLE 4-Nitroanisole> 4-Nitroanisole,97% 4-Nitroanisole,100-17-4 Nitroanisole 1-METHOXY-4-NITROBENZENE 4-Nitroanisole,98% 1,12-DIOCTANOYL-SN-GLYCEROL PARA-NITROANISOLE 4-Nitroanisol Phloroglucinol Impurity 188 100-17-4 000100-02-1 Nitrogen Compounds Organic Building Blocks Nitro Compounds Building Blocks Aromatic Ethers