α-(p-Aminophenyl)butyric acid Chemical Properties

Melting point:

142-143℃

Boiling point:

354.6±17.0 °C(Predicted)

Density 

1.171±0.06 g/cm3 (20 ºC 760 Torr)

vapor pressure 

13-18hPa at 20-25℃

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.01±0.10(Predicted)

form 

Solid:particulate/powder

Appearance

White to off-white Solid

InChI

InChI=1S/C10H13NO2/c1-2-9(10(12)13)7-3-5-8(11)6-4-7/h3-6,9H,2,11H2,1H3,(H,12,13)

InChIKey

WAPLXGPARWRGJO-UHFFFAOYSA-N

SMILES

C1(C=CC(N)=CC=1)C(CC)C(=O)O

LogP

-1.3 at 19.8℃ and pH7

Surface tension

75.21mN/m at 1g/L and 20℃

Safety Information

Toxicity

mouse,LD50,intraperitoneal,1180mg/kg (1180mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958.

α-(p-Aminophenyl)butyric acid Usage And Synthesis

Pharmaceutical Applications

α-(p-Aminophenyl)butyric acid can be used as a ligand for the development of GABA receptor modulators, which are crucial in the treatment of neurological disorders. Its structural similarity to GABA allows it to interact with GABA receptors, potentially modulating their activity and offering therapeutic benefits.

Synthesis

2-(4-Nitrophenyl)butyric acid (10.0 g, 47.8 mmol) and carbon-loaded palladium catalyst (0.25 g) were suspended in methanol (100 mL). The reaction mixture was stirred overnight at room temperature and 1 atm hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the diatomaceous earth was washed with methanol (50 mL). The filtrates were combined and concentrated using a rotary evaporator. Water (200 mL) was added to the concentrate and recrystallized. The mixture was cooled in an ice bath to precipitate a pink solid product. The solid was collected by vacuum filtration and dried under vacuum to give 5.8 g of 2-(4-aminophenyl)butyric acid in 68% yield. The product was characterized by the following data: NMR (400 MHz, DMSO-d6) δ 11.88 (s, 1H, COOH), 6.73 (d, J = 8.4 Hz, 2H, ArH), 6.31 (d, J = 8.4 Hz, 2H, ArH), 4.77 (s, 2H, NH2), 2.98 (t, J = 7.5 Hz, 1H, CH). 1.68 (m, 1H, CH2), 1.39 (m, 1H, CH2), 0.62 (t, J = 7.3 Hz, 3H, CH3); MS (ESI) m/z 202.1 ([M+Na]+).

References

[1] Patent: WO2017/205451, 2017, A1. Location in patent: Paragraph 0293
[2] Bulletin de la Societe Chimique de France, 1927, vol. <4> 41, p. 451
[3] Patent: US5214191, 1993, A
[4] Patent: CN106631974, 2017, A. Location in patent: Paragraph 0028; 0029; 0031; 0032; 0033

α-(p-Aminophenyl)butyric acid(29644-97-1)Related Product Information

• 2-(4-NITROPHENYL)BUTYRIC ACID
• Indobufen
• Phthalic acid
• CIS-BUTENEDIOIC ANHYDRIDE
• Benzeneacetic acid, α-ethyl-2-nitro-
• Indobufen Impurity 9
• Indobufen Impurity 23
• Benzeneacetic acid, 4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-α-ethyl-, ethyl ester
• 2-[4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)phenyl]butyric acid
• Benzeneacetonitrile, 4-amino-α-ethyl-
• Indobufen Impurity A
• Benzeneacetic acid, 4-(1,3-dihydro-1-oxo-2H-isoindol-2-yl)-α-ethyl-, ethyl ester
• ethyl 2-(4-nitrophenyl)butanoate
• Benzeneacetic acid, α-ethyl-3-nitro-
• Benzeneacetonitrile, α-ethyl-2-nitro-
• Benzeneacetonitrile, α-ethyl-4-nitro-
• Indobufen Impurity 2
• 4-Nitrophenylacetic acid