4,5-DIFLUORO-2-NITROANILINE Chemical Properties

Melting point:

107-108 °C (lit.)

Boiling point:

308.1±37.0 °C(Predicted)

Density 

1.554±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

pka

-1.25±0.25(Predicted)

form 

Crystalline Powder

color 

Golden to orange

BRN 

2723242

InChI

InChI=1S/C6H4F2N2O2/c7-3-1-5(9)6(10(11)12)2-4(3)8/h1-2H,9H2

InChIKey

WDMCABATCGQAKK-UHFFFAOYSA-N

SMILES

C1(N)=CC(F)=C(F)C=C1[N+]([O-])=O

CAS DataBase Reference

78056-39-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

2811

WGK Germany 

3

F 

10

Hazard Note 

Irritant

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214200

MSDS

• Language:English Provider:SigmaAldrich

4,5-DIFLUORO-2-NITROANILINE Usage And Synthesis

Chemical Properties

Golden to orange crystalline powder

Uses

4,5-Difluoro-2-nitroaniline has been used in the preparation of:

• 2-chloro-5,6-difluorobenzimidazole
• 1-(4,5-difluoro-2-nitrophenyl)pyrene via diazotization reaction with isoamyl nitrite in the presence of pyrene
• 5-ethoxy-6-fluorobenzofuroxan

Synthesis

General procedure for the synthesis of 2-nitro-4,5-difluoroaniline from 2,4,5-trifluoronitrobenzene: Ammonia (15 mL) was added to a solution of 1,2,4-trifluoro-5-nitrobenzene (1) (5.00 g, 28.0 mmol, 1.00 eq.) in methanol (5 mL) and the mixture was transferred to a microwave reaction flask. The reaction mixture was placed in a microwave reactor and heated at 70 °C for 90 min. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane, 1:4) to afford the target compound 2 (0.600 g, 12.0% yield) as a yellow solid. Thin layer chromatography (TLC) analytical conditions: 30% ethyl acetate/hexane (Rf value: 0.35); 1H NMR (500 MHz, CDCl3) data: δ 8.00 (t, J = 9.0 Hz, 1H), 6.65-6.58 (m, 1H), 6.08 (br s, 2H).

References

[1] Patent: US2013/287686, 2013, A1. Location in patent: Paragraph 0144; 0145
[2] Journal of Medicinal Chemistry, 1965, vol. 8, p. 737 - 740
[3] Patent: US2018/185362, 2018, A1. Location in patent: Paragraph 0556; 0557; 0558; 0559

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