ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluoroaniline series 4-Fluoroaniline

4-Fluoroaniline

Product Name4-Fluoroaniline
CAS371-40-4
MFC6H6FN
MW111.12
EINECS206-735-5
MOL File371-40-4.mol

Chemical Properties

Melting point	−1.9 °C (28.6 °F; 271.2 K)
Boiling point	188 °C (370 °F; 461 K)
Density	1.1725 g/cm3
refractive index	1.54
Flash point	73 °C
storage temp.	2-8°C
solubility	33g/l
pka	4.65(at 25℃)
form	liquid
color	colorless
Specific Gravity	1.173
Water Solubility	33 g/L (20 ºC)
Merck	14,4169
BRN	742030
Henry's Law Constant	1.6×10⁰ mol/(m³Pa) at 25℃, HSDB (2015)
Stability	Stable. Incompatible with acids, oxidizing agents.
InChI	1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
InChIKey	KRZCOLNOCZKSDF-UHFFFAOYSA-N
SMILES	Nc1ccc(F)cc1
CAS DataBase Reference	371-40-4(CAS DataBase Reference)
NIST Chemistry Reference	p-Fluoroaniline(371-40-4)
EPA Substance Registry System	p-Fluoroaniline (371-40-4)

Safety Information

Hazard Codes	C,T,Xi,Xn
Risk Statements	22-34-36/38-33-23/24/25
Safety Statements	26-36/37/39-45-37/39-28
RIDADR	UN 2941
WGK Germany	1
RTECS	BY1575000
Hazard Note	Toxic/Irritant
TSCA	TSCA listed
HazardClass	6.1
PackingGroup	III
HS Code	29214210
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1 Skin Corr. 1C STOT RE 2
Hazardous Substances Data	371-40-4(Hazardous Substances Data)

MSDS

Provider	Language
4-Fluorobenzenamine	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

4-Fluoroaniline is a light yellow to gold-coloured liquid.It is easy to oxidize and turn red in air.

Uses

4-Fluoroaniline is a degradation product of Ezetimibe (E975000). 4-Fluoroaniline is used as an analytical reagent in the enzymic detection of glucose.

Uses

4-Fluoroaniline may be employed as one of the target pollutant during the investigation of biodegradability of fluorinated compounds under aerobic conditions. It may be used for the synthesis of luminescent and cationic monocyclometalated gold(III) monoaryl complexes.

Uses

Intermediate in the manufacture of herbicides and plant growth regulators.

Preparation

The better process in the one-step process is the nitrobenzene method, which is obtained by deoxygenation, hydrogenation and fluorination. With PdCl2-V2O5 as the catalyst and carbon monoxide as the reducing agent, the reaction was carried out at 160°C for 3h, and the yield of 4-fluoroaniline could reach 90%, with another 10% of aniline as a by-product. With PtO2 as the catalyst, BF3-HF as the fluorinating agent and hydrogen as the reducing agent, the reaction was carried out at 42℃ for 12.5h, with 100% conversion and 95% yield.

Definition

ChEBI: 4-fluoroaniline is a primary arylamine that is the derivative of aniline in which the hydrogen at position 4 has been substituted by fluorine. It is used as an intermediate in the manufacture of pharmaceuticals, herbicides and plant growth regulators. It is a primary arylamine and a fluoroaniline.

Synthesis Reference(s)

Journal of the American Chemical Society, 70, p. 654, 1948 DOI: 10.1021/ja01182a065
The Journal of Organic Chemistry, 26, p. 4014, 1961 DOI: 10.1021/jo01068a089

General Description

4-fluoroaniline is a light-colored oily liquid. Mixture of three isomers. Insoluble in water and denser than water. Contact may cause irritation to skin, eyes, and mucous membranes. May be toxic by ingestion. Used to make other chemicals. The barriers to inversion and internal rotation of the NH2 group in 4-fluoroaniline has been investigated by far infrared gas spectra.

Hazard

Toxic material.

Flammability and Explosibility

Not classified

Safety Profile

Poison by ingestion. Mutation data reported. A severe skin and eye irritant. When heated to decomposition it emits very toxic fumes of NOx and F-.

4-Fluoroaniline

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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