2-(4-NITROPHENYL)PROPIONIC ACID

2-(4-NITROPHENYL)PROPIONIC ACID Property

Melting point:

88-89 °C(lit.)

Boiling point:

361.9±25.0 °C(Predicted)

Density 

1.337±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethanol

form 

Solid

pka

3.91±0.10(Predicted)

color 

Light Orange

InChI

InChI=1S/C9H9NO4/c1-6(9(11)12)7-2-4-8(5-3-7)10(13)14/h2-6H,1H3,(H,11,12)

InChIKey

RBSRRICSXWXMRC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

19910-33-9(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2916399090

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

2-(4-NITROPHENYL)PROPIONIC ACID Chemical Properties,Usage,Production

Uses

2-(4-Nitrophenyl)propionic acid is a reagent used in the preparation of α-Methylated analogs of triiodothyroalkanoic acids which have interactions with hepatic thyroid receptors.

Uses

2-(4-Nitrophenyl)propionic acid may be used in chemical synthesis.

Synthesis

Ethyl 2-(4-nitrophenyl)propionate (4.5 g, 20.17 mmol, 1.0 eq.) was used as raw material and dissolved in ethanol (40 ml). To this solution NaOH (1.614 g, 40.35 mmol, 2.0 eq.) and water (10 ml) were added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and subsequently diluted with the addition of water. The pH of the reaction mixture was adjusted to acidic with dilute hydrochloric acid. The product was extracted with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by column chromatography to give α-methyl-4-nitrophenylacetic acid (3.1 g, 78.8% yield). Mass spectrum (electrospray ionization): m/z 195.17 [M + H]+.

References

[1] Patent: US2016/251376, 2016, A1. Location in patent: Paragraph 0625; 0628; 0629