ChemicalBook Product Catalog Biochemical Engineering Amino Acids and Derivatives Other amino acid derivatives 4-(4-Aminophenyl)butyric acid

4-(4-Aminophenyl)butyric acid

Product Name4-(4-Aminophenyl)butyric acid
CAS15118-60-2
MFC10H13NO2
MW179.22
EINECS628-142-4
MOL File15118-60-2.mol

Chemical Properties

Melting point	121-124 °C (lit.) 121-133 °C
Boiling point	363.7±17.0 °C(Predicted)
Density	1.177±0.06 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
solubility	DMSO (Slightly), Methanol (Slightly)
form	Solid
pka	4.70±0.10(Predicted)
color	Light Beige to Light Brown
Major Application	peptide synthesis
InChI	InChI=1S/C10H13NO2/c11-9-6-4-8(5-7-9)2-1-3-10(12)13/h4-7H,1-3,11H2,(H,12,13)
InChIKey	RBHLFWNKEWLHBP-UHFFFAOYSA-N
SMILES	C1(CCCC(O)=O)=CC=C(N)C=C1
CAS DataBase Reference	15118-60-2(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-37/39
WGK Germany	3
HS Code	2922498590
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

4-(4-Aminophenyl)butyric acid (4-APB) is an important organic compound derived from butyric acid, which is used as a synthetic intermediate for pharmaceuticals or the synthesis of various compounds. It is also used in drug mechanism studies and is thought to be an agonist for certain G-protein coupled receptors and may also interact with other proteins in the signal transduction pathway. In addition, 4-(4-aminophenyl)butyric acid has been found to inhibit monoamine oxidase, which plays a role in neurotransmitter catabolism.

Uses

4-(4-Aminophenyl)butyric Acid is a degradation product of Chlorambucil (C325050); an alkylating agent that is used as an chemotherapy drug in the treatment of chronic lymphocytic leukemia. Chlorambucil is also used to treat non-Hodgkin''s lymphoma (NHL) and Hodgkin''s disease.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

5473-15-4

15118-60-2

The general procedure for the synthesis of 4-(4-aminophenyl)butyric acid from 4-(4-acetamidophenyl)-4-oxobutanoic acid was as follows: 89 g of 3-(4-acetamidophenyl)propionic acid, 88 g of potassium hydroxide, 65 ml of 85% hydrazine hydrate and 450 ml of diethylene glycol were mixed and heated and refluxed for 1.5 hours. Subsequently, the reaction temperature was raised to 150°C to remove excess hydrazine hydrate and the reaction was maintained at this temperature for 4 hours. Upon completion of the reaction, it was cooled to room temperature, 400 g of water was added, and the pH was adjusted to 6 with 6N hydrochloric acid, and then adjusted to 5-6 with glacial acetic acid. at this point, the target product precipitated as crystals, and after filtration, washing and drying, 44 g of white or near-white crystals were obtained in 95% yield.

References

[1] Patent: CN104447376, 2016, B. Location in patent: Paragraph 0032-0033; 0043-0044
[2] European Journal of Medicinal Chemistry, 2018, vol. 146, p. 588 - 598

4-(4-Aminophenyl)butyric acid

Chemical Properties

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MSDS

Usage And Synthesis

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