2,5-Difluoroaniline Chemical Properties

Melting point:

11-13 °C (lit.)

Boiling point:

176-178 °C (lit.)

Density 

1.288 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.513(lit.)

Flash point:

156 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

2.19±0.10(Predicted)

form 

clear liquid

color 

Colorless to Yellow to Orange

Specific Gravity

1.29

Water Solubility 

Not miscible in water.

BRN 

2802549

InChI

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

InChIKey

YNOOQIUSYGWMSS-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=CC=C1F

CAS DataBase Reference

367-30-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 2,5-difluoro-(367-30-6)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

28-36/37/39-26-36

RIDADR 

2941

WGK Germany 

3

F 

8-10-23

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214210

MSDS

• Language:English Provider:2,5-Difluoroaniline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,5-Difluoroaniline Usage And Synthesis

Chemical Properties

clear brown liquid

Uses

2,5-Difluoroaniline was used in the synthesis of 2,4-di-tert-butyl-6-[(2,5-difluorophenyl)iminomethyl]phenol. It was also used in ultrasound-assisted preparation of 1,4-diazabutadienes. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Synthesis

General procedure for the synthesis of 2,5-difluoroaniline from 2,5-difluoronitrobenzene: To a solution of 1,4-difluoro-2-nitrobenzene (500 mg, 3.14 mmol) in methanol (20 mL) was added palladium/carbon catalyst (66.9 mg, 0.629 mmol) in batches. Subsequently, the reaction mixture was stirred at 20 °C for 1 h under hydrogen atmosphere. The reaction progress was monitored by thin layer chromatography (TLC, petroleum ether/ethyl acetate = 3/1) and after confirming the complete consumption of raw materials, the reaction mixture was filtered. The filtrate was concentrated to afford the target product 2,5-difluoroaniline (338 mg, 2.61 mmol, 83% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 6.94-6.88 (m, 1H), 6.50-6.46 (m, 1H), 6.40-6.31 (m, 1H), 3.82 (br.s., 2H).

References

[1] Patent: US2014/275111, 2014, A1. Location in patent: Paragraph 0485; 0486
[2] Patent: WO2014/141187, 2014, A1. Location in patent: Page/Page column 109
[3] Recueil des Travaux Chimiques des Pays-Bas, 1914, vol. 33, p. 299
[4] Chem. Zentralbl., 1914, vol. 85, # II, p. 320
[5] Journal fuer Praktische Chemie (Leipzig), 1934, vol. <2> 140, p. 97,111

2,5-Difluoroaniline(367-30-6)Related Product Information

• N,N-Dimethylaniline
• Diphenylamine
• 3-Fluoroaniline
• 4-(Trifluoromethoxy)aniline
• N,N-Dimethyl-1,4-phenylenediamine
• 2-Fluoroaniline
• Sodium diphenylamine-4-sulfonate
• 2-Aminobenzotrifluoride
• 4-Fluoroaniline
• PENTAFLUORONITROBENZENE
• 1,2,4-Trifluoro-5-nitrobenzene
• PENTAFLUOROPHENYLHYDRAZINE
• 3,4-Difluoroaniline
• 2,3,5,6-TETRAFLUOROPHENYLHYDRAZINE
• 4-AMINO-2,3,5,6-TETRAFLUOROBENZAMIDE
• 3,5-Difluoroaniline
• 2,3-DIFLUOROANILINE
• 2,4-Difluoroaniline