4-Fluoroaniline Property

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)

Safety

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P314Get medical advice/attention if you feel unwell.

4-Fluoroaniline Chemical Properties,Usage,Production

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-.