ChemicalBook Product Catalog Organic Chemistry Organic fluorine compound Fluoroaniline series 3,4-Difluoroaniline

3,4-Difluoroaniline

Product Name3,4-Difluoroaniline
CAS3863-11-4
MFC6H5F2N
MW129.11
EINECS223-381-7
MOL File3863-11-4.mol

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)
color	White or Colorless to Yellow
Specific Gravity	1.302
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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

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

369-34-6

3863-11-4

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

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