METHYL 4-(4-AMINOPHENYL)BUTANOATE Chemical Properties

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)

Safety Information

HS Code 

2922498590

METHYL 4-(4-AMINOPHENYL)BUTANOATE Usage And Synthesis

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

METHYL 4-(4-AMINOPHENYL)BUTANOATE(20637-09-6)Related Product Information

• 4-Phenylbutyric acid
• ETHYL 4-(4-NITROPHENYL)-4-OXOBUTYRATE
• ETHYL 4-[4-(N,N-DIMETHYLAMINO)PHENYL]-4-OXOBUTANOATE
• CYCLOPROPANECARBOXYLIC ACID, 2-(4-NITROPHENYL), ETHYL ESTER
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• METHYL 4-(4-(BIS(2-HYDROXYETHYL)AMINO)PHENYL)BUTYRATE
• METHYL 4-(4-NITROPHENYL)-2,4-DIOXOBUTANOATE
• 4-(4-NITRO-PHENYL)-3-OXO-BUTYRIC ACID METHYL ESTER
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• 4-(4-NITRO-PHENYL)-3-OXO-BUTYRIC ACID ETHYL ESTER
• ETHYL 4-(4-AMINOPHENYL)BUTANOATE