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4-Fluoroaniline

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4-Fluoroaniline Basic information

Product Name:
4-Fluoroaniline
Synonyms:
  • 1,4-fluorobenzenamine
  • 4-Fluoranilin
  • 4-fluoranilin(czech)
  • 4-fluoro-anilin
  • 4-fluoro-benzenamin
  • 4-Fluoronaniline
  • Aniline, 4-fluoro-
  • Aniline, p-fluoro-
CAS:
371-40-4
MF:
C6H6FN
MW:
111.12
EINECS:
206-735-5
Product Categories:
  • Fluorobenzene
  • Amines
  • Aromatics
  • Impurities
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Fluoro-Aromatics
  • Anilines, Aromatic Amines and Nitro Compounds
  • Fluorine series
  • amine | alkyl Fluorine
  • Amines, Aromatics, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
  • K00001
Mol File:
371-40-4.mol
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4-Fluoroaniline Chemical Properties

Melting point:
-1.9 °C
Boiling point:
187 °C/767 mmHg (lit.)
Density 
1.173 g/mL at 25 °C (lit.)
refractive index 
n20/D 1.539(lit.)
Flash point:
165 °F
storage temp. 
2-8°C
solubility 
33g/l
pka
4.65(at 25℃)
form 
Oily Liquid
Specific Gravity
1.173
color 
Clear pale yellow to red-brown
Water Solubility 
33 g/L (20 ºC)
Merck 
14,4169
BRN 
742030
Stability:
Stable. Incompatible with acids, oxidizing agents.
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)
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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 6.1/PG 3
WGK Germany 
1
RTECS 
BY1575000
Hazard Note 
Toxic/Irritant
TSCA 
T
HazardClass 
6.1
PackingGroup 
III
HS Code 
29214210
Hazardous Substances Data
371-40-4(Hazardous Substances Data)

MSDS

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4-Fluoroaniline 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-.

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