4-(4-Aminophenyl)butyric acid CAS 15118-60-2
4-(4-Aminophenyl)butyric acid Basic information
| Product Name: | 4-(4-Aminophenyl)butyric acid |
| Synonyms: | 4-(4-Aminophenyl)butanoicacid;4-(4-Aminophenyl)butyric acid, ≥95.0%;p-Aminophenylbutyricacid;AKOS BB-8810;4-(4-AMINOPHENYL)BUTYRIC ACID;4-Aminophenylbutyric Acid;4-Aminobenzenebutanoic acid;4-Amino-benzenebutanoic |
| CAS: | 15118-60-2 |
| MF: | C10H13NO2 |
| MW: | 179.22 |
| EINECS: | 628-142-4 |
| Product Categories: | Others;Peptide Synthesis;Unnatural Amino Acid Derivatives |
| Mol File: | 15118-60-2.mol |
4-(4-Aminophenyl)butyric acid 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) |
| pka | 4.70±0.10(Predicted) |
| form | Solid |
| 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 |
| 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 Preparation Products And Raw materials
| Raw materials | Acetic acid-->Aluminium chloride hexahydrate-->Succinic anhydride-->Acetanilide-->2-BENZOYLACETANILIDE-->3-(4-ACETYLAMINOBENZOYL)PROPANOIC ACID-->Diethylene glycol-->Hydrazine hydrate-->Potassium hydroxide |
| Preparation Products | METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE-->METHYL 4-(4-AMINOPHENYL)BUTANOATE |
