3,4-Difluoroaniline Chemical Properties

Melting point:

22°C

Boiling point:

77 °C/7 mmHg (lit.)

Density 

1.302 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.513(lit.)

Flash point:

185 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to lump to clear liquid

pka

3?+-.0.10(Predicted)

Specific Gravity

1.302

color 

White or Colorless to Yellow

Water Solubility 

SLIGHTLY SOLUBLE

BRN 

971235

InChI

InChI=1S/C6H5F2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2

InChIKey

AXNUZKSSQHTNPZ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(F)C(F)=C1

CAS DataBase Reference

3863-11-4(CAS DataBase Reference)

NIST Chemistry Reference

3,4-Difluoroaniline(3863-11-4)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

26-36-36/37/39

RIDADR 

UN 2941 6.1/PG 3

WGK Germany 

3

RTECS 

CX9871900

F 

8-10-23

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4-Difluoroaniline Usage And Synthesis

Chemical Properties

clear yellow to straw liquid after melting

Uses

3,4-Difluoroaniline was used in the synthesis of (3,4-disfluoro)phenylquione.

General Description

3,4-Difluoroaniline (3,4-DFA) was degraded, under aerobic conditions, by Pseudomonas fluorescens.

Synthesis

The general procedure for the synthesis of 3,4-difluoroaniline from 3,4-difluoronitrobenzene was as follows: 200.0 g of 3,4-difluoronitrobenzene, 600.0 mL of toluene and 12.0 g of Pd/C catalyst were added to an autoclave at 25 °C to 35 °C. Hydrogen was passed into the reaction system, keeping the hydrogen pressure between 2.0 and 6.0 kg/cm2, and the reaction was carried out at 25 °C to 35 °C for 3 to 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) to ensure complete reaction. Upon completion of the reaction, the reaction mixture was sequentially depressurized and unloaded, filtered through a Hyflow bed, and the filter cake was washed with 200.0 mL of toluene. The filtrate was collected and vacuum distilled at less than 50 °C to remove the solvent. Finally, 152.0 g of crude 3,4-difluoroaniline was obtained in 93.8% yield and 95.85% purity by high performance liquid chromatography (HPLC).

References

[1] Patent: WO2015/68171, 2015, A1. Location in patent: Page/Page column 9; 16
[2] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 613 - 617
[4] ChemPlusChem, 2018, vol. 83, # 5, p. 375 - 382
[5] Synthesis, 2001, # 1, p. 81 - 84

3,4-Difluoroaniline(3863-11-4)Related Product Information

• 3-Aminobenzotrifluoride
• Sodium diphenylamine-4-sulfonate
• 3-Fluoroaniline
• 4-(Trifluoromethoxy)aniline
• N,N-Dimethyl-1,4-phenylenediamine
• 2-Fluoroaniline
• Diphenylamine
• 4-Fluoroaniline
• N,N-Dimethylaniline
• 2,3,4-Trifluorobenzenamine
• 2,3,4,5,6-Pentafluoroaniline
• 2-BROMO-4,5,6-TRIFLUOROANILINE
• N,N'-BIS(PENTAFLUOROPHENYL)UREA
• 2,4,5-Trifluoroaniline
• 2,4,5-TRIFLUORO-6-BROMOANILINE
• 3,4-Difluoronitrobenzene
• 2,3-DIFLUOROANILINE
• 2,5-Difluoroaniline