6-Nitrophthalide

6-Nitrophthalide Property

Melting point:

140-145 °C(lit.)

Boiling point:

311.63°C (rough estimate)

Density 

1.4908 (rough estimate)

refractive index 

1.5160 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

Pale yellow

Water Solubility 

0.4g/L(25 ºC)

CAS DataBase Reference

610-93-5(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-37-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29322090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

6-Nitrophthalide Chemical Properties,Usage,Production

Chemical Properties

pale yellow crystalline powder

Uses

6-Nitrophthalide is a fluorescent heterocycle that can be used as a probe for specific inhibition. It is homologous to other fluorescent probes such as fluorescein, nitrobenzene, and nitrophenol. It has been shown to have inhibitory properties against triazole and dipole, which are catalytic asymmetric. 6-Nitrophthalide has also been shown to have the ability to inhibit the oxidation of aldehydes.

Preparation

6-Nitrophthalide is synthesized from 2-nitrobenzaldehyde via a two-step process, and then reacted with methyl iodide.

Application

6-Nitrophthalide has been used in the preparation of 3-bromo-6-nitrophthalide. It undergoes reductive methylation to form 6-dimethylaminophthalide.

Synthesis

Step A: Synthesis of 6-nitrobenzofuran-1(3H)-one 1. dissolve phthalide (40.0 g, 298 mmol) in sulfuric acid (50.0 mL) under ice bath conditions and stir until homogeneous. 2. dissolve potassium nitrate (30.4 g, 300 mmol) in sulfuric acid (80 mL) and add to the above sulfuric acid solution of phthalide by dropping. 3. Keeping the reaction mixture under stirring, the reaction mixture was slowly warmed up to room temperature, which took about 5 hours. 4. Upon completion of the reaction, the mixture was slowly poured into ice water to precipitate. 5. The precipitate was collected and recrystallized from ethanol (3 L) to give 6-nitrobenzofuran-1(3H)-one (50.4 g, 94% yield) as an off-white solid. 6. The structure and purity (98%) of the product were confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 500 MHz, CDCl3) with the following characteristic peaks: δ 8.77 (d, J = 1.5 Hz, 1H), 8.58 (dd, J = 8.5, 2.0 Hz, 1H), 7.72 (d, J = 8.5 Hz, 1H), 5.45 (s, 2H).

References

[1] Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993, vol. 335, # 1, p. 17 - 22
[2] Patent: WO2012/142459, 2012, A1. Location in patent: Page/Page column 37
[3] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1519 - 1523
[4] Patent: US2008/9524, 2008, A1. Location in patent: Page/Page column 409
[5] Patent: US2011/98311, 2011, A1