| Identification | Back Directory | [Name]
METHYL 4-(4-AMINOPHENYL)BUTANOATE | [CAS]
20637-09-6 | [Synonyms]
Einecs 243-933-0
Methyl 4-aminobenzenebutanoate
METHYL 4-(4-AMINOPHENYL)BUTYARTE
Methyl 4-(4-aminophenyl)butyrate
Methyl 4-(4-Aminopheny)Butanoate
METHYL 4-(4-AMINOPHENYL)BUTANOATE
4-aminophenylbutyricacidmethylester
4-(4-Aminophenyl)butyricacidmethylester
4-Aminobenzenebutyric acid methyl ester
p-Aminobenzenebutanoic acid methyl ester
4-(4-Aminophenyl)butanoic acid methyl ester
Benzenebutanoic acid, 4-amino-, methyl ester
Butyric acid, 4-(p-aminophenyl)-, methyl ester | [EINECS(EC#)]
243-933-0 | [Molecular Formula]
C11H15NO2 | [MDL Number]
MFCD07366753 | [MOL File]
20637-09-6.mol | [Molecular Weight]
193.24 |
| Chemical Properties | Back Directory | [Melting point ]
42 °C(Solv: ligroine (8032-32-4)) | [Boiling point ]
323.9±25.0 °C(Predicted) | [density ]
1.088±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
4.83±0.10(Predicted) | [Appearance]
Brown to dark brown <42°C Solid,>42°C Liquid | [InChI]
InChI=1S/C11H15NO2/c1-14-11(13)4-2-3-9-5-7-10(12)8-6-9/h5-8H,2-4,12H2,1H3 | [InChIKey]
CLKHQWJXESOLCJ-UHFFFAOYSA-N | [SMILES]
C1(CCCC(OC)=O)=CC=C(N)C=C1 | [NIST Chemistry Reference]
4-(4-Aminophenyl)butanoic acid methyl ester(20637-09-6) |
| Hazard Information | Back Directory | [Chemical Properties]
Needle-shaped crystals. Melting point 42°C. | [Uses]
Methyl 4-(4-Aminophenyl)butanoate is used in the synthesis of derivative of chlorambucil, a selective anti-cancer drug toward chondrosarcoma that would concentrate in this malignant cartilaginous tissue. | [Synthesis]
b) Synthesis of methyl 4-(4-aminophenyl)butyrate
Methyl 4-(4-nitrophenyl)butyrate (3.05 g, 13.67 mmol) and Pd/C catalyst (1.0 g, 10% Pd, activated carbon carrier, 1.09 mmol) were suspended in methanol (40 mL). The reaction mixture was stirred under hydrogen atmosphere (balloon pressure) for 1 hour. After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad (washed with ethyl acetate). The filtrate was concentrated under reduced pressure to give 2.33 g of methyl 4-(4-aminophenyl)butyrate (brown solid, yield: 88%). The product did not require further purification and could be used directly in the next step of the reaction.
1H NMR (CDCl3, 250MHz) δppm: 6.96 (d, J=8.5Hz, 2H), 6.63 (d, J=8.2Hz, 2H), 3.66 (s, 3H), 2.55 (t, J=7.6Hz, 2H), 2.31 (t, J=7.7Hz, 2H), 1.90 (q, J=7.6Hz, 2H). | [References]
[1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 17, p. 6463 - 6480
[2] Patent: WO2009/80722, 2009, A2. Location in patent: Page/Page column 52
[3] Journal of Pharmaceutical Sciences, 1988, vol. 77, # 2, p. 185 - 187
[4] Journal of the Chemical Society, 1953, p. 2386,2387
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3014 - 3019 |
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