7-Fluoro-6-nitro-4-hydroxyquinazoline Chemical Properties

Melting point:

282-285 °C(Solv: acetic acid (64-19-7))

Boiling point:

407.6±55.0 °C(Predicted)

Density 

1.75±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

powder to crystal

pka

-2.69±0.20(Predicted)

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C8H4FN3O3/c9-5-2-6-4(1-7(5)12(14)15)8(13)11-3-10-6/h1-3H,(H,10,11,13)

InChIKey

VTUAEMSZEIGQRM-UHFFFAOYSA-N

SMILES

N1C2=C(C=C([N+]([O-])=O)C(F)=C2)C(=O)NC=1

CAS DataBase Reference

162012-69-3(CAS DataBase Reference)

Safety Information

Risk Statements 

36

Safety Statements 

26

HS Code 

2933599590

7-Fluoro-6-nitro-4-hydroxyquinazoline Usage And Synthesis

Uses

7-Fluoro-6-nitroquinazolin-4(3H)-one, is an intermediate in the preparation of kinase inhibitors, such as ATP Site inhibitors of the Tyrosine Kinase activity of the epidermal growth factor receptor.

Synthesis

General procedure for the synthesis of 7-fluoro-6-nitro-4-hydroxyquinazoline from 2-amino-4-fluorobenzoic acid: 2-amino-4-fluorobenzoic acid (25 g, 152 mmol) was slowly added dropwise to a mixed solution of concentrated sulfuric acid (50 mL) and concentrated nitric acid (51 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1 hour and then warmed to 110°C and continued stirring for 2 hours. Upon completion of the reaction, the mixture was cooled to room temperature and quenched by slowly adding ice water (300 mL). The resulting mixture was continued to be stirred for 30 min, followed by filtration to give 7-fluoro-6-nitro-4-hydroxyquinazoline solid product (25 g, 79% yield). The structure of the product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (NMR, 300 MHz, CDCl3) and mass spectrometry (MS, ESI+): NMR data: δ 12.83 (broad single peak, 1H), 8.72 (double peak, 1H), 8.32 (single peak, 1H), 7.79 (double peak, 1H); MS data: m/z 210 [M+H]+.

References

[1] Patent: WO2012/30160, 2012, A2. Location in patent: Page/Page column 25
[2] Journal of Medicinal Chemistry, 1996, vol. 39, # 4, p. 918 - 928
[3] Patent: WO2012/182, 2012, A1
[4] Patent: WO2012/356, 2012, A1
[5] Patent: EP2612860, 2013, A1

7-Fluoro-6-nitro-4-hydroxyquinazoline(162012-69-3)Related Product Information

• Cefazolin
• Cefazolin sodium salt
• 4-Hydroxyquinazoline
• NITROGEN DIOXIDE
• Fluorine
• 7-Fluoro-4-quinazolone
• 6-AMINO-3H-QUINAZOLIN-4-ONE
• 4-FLUORO-3-NITROBENZALDEHYDE
• 6-NITROQUINAZOLIN-4(3H)-ONE
• 2(1H)-Quinazolinone (6CI,8CI,9CI)
• (4-FLUORO-3-NITROPHENYL) METHANAMINE
• (3-fluoro-4-nitrophenyl)methanamine
• Benzenemethanamine, 2-amino-4-fluoro- (9CI)
• 2-AMINO-4-FLUORO-5-NITROTOLUENE
• 3-amino-4-fluorobenzamide
• 4-FLUORO-3-NITROBENZAMIDE
• 7-Fluoro-6-nitro-4-hydroxyquinazoline