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CAS No. : | 56-12-2 | MDL No. : | MFCD00008226 |
Formula : | C4H9NO2 | Boiling Point : | - |
Linear Structure Formula : | H2N(CH2)3CO2H | InChI Key : | BTCSSZJGUNDROE-UHFFFAOYSA-N |
M.W : | 103.12 | Pubchem ID : | 119 |
Synonyms : |
4-Aminobutyric acid;GABA;Mielomade;Mielogen;DF 468;Aminalon;Piperidic acid;Gamma-aminobutyric acid;4-Aminobutanoic acid
|
Chemical Name : | 4-Aminobutyric acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triethylamine; In ethanol;Reflux; | General procedure: 4-Amino butanoic acid (GABA) was dissolved in ethyl alcohol followed by addition of II (i-xi) (0.01 M) and triethylamine (0.01 mol). The reaction mixture was refluxed for 6-7 h. The reaction mixture was poured on crushed ice. The resulting solid was separated, dried, and recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium methylate; In methanol;Reflux; | A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) and 4-aminobutyric acid (525 mg, 5.1 mmol) in 0.5 N NaOMe in MeOH solution (6.8 mL, 3.4 mmol) was heated to reflux overnight. Reaction mixture was diluted with water (100 mL) and acidified by 1 N HC1 solution to pH = 3-4. Precipitate was collected and rinsed with water. It was dried in vacuo to provide the title compound (117 mg, 0.32mmol) in 94% yield. LC-MS ESI-: 365.05 (M-l) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine; In tetrahydrofuran; water; for 4h; | To a solution of BCN-OSu (1 .00 g, 3.43 mmol) in a mixture of THF and water (80 mL/80 mL) were added γ-aminobutyric acid (0.60 g, 5.12 mmol) and Et3N (1.43 mL, 1.04 g, 10.2 mmol). The mixture was stirred for 4 h followed by addition of DCM (200 mL) and a saturated aqueous solution of NhUCI (80 mL). After separation, the aqueous layer was extracted with DCM (2x200 mL). The combined organic layers were dried (Na2S04) and concentrated. The residue was purified with column chromatography (MeOH in DCM 0→ 10%). The product was obtained as a colourless thick oil (730 mg, 2.61 mmol, 76%). NMR (400 MHz, CDCI3) δ (ppm) 4.81 (bs, 1 H), 4.15 (d, J = 8.4 Hz, 2H), 3.30-3.21 (m, 2H), 2.42 (t, J = 7.2 Hz, 2H), 2.35-2.16 (m, 6H), 1.85 (quintet, J = 6.9 Hz, 2H), 1.64- 1.51 (m, 2H), 1.35 (quintet, J = 8.4 Hz, 1 H), 1.00-0.90 (m, 2H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; for 3h; | General procedure: Phthalic anhydride or its derivatives (2.0 mmol) and 4-aminobutyric acid (2.0 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h. The reaction was quenched with water (10 mL) and was adjusted to pH 6-8 with NaOH (0.1 mol/L). The mixture was extracted with dichloromethane (10 mL × 3), and the organic layer was washed with aq. NaHCO3, and water and then evaporated to afford intermediate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.5% | With acetic acid; at 100℃; for 3h; | 3-Chlorophthalic anhydride (365 mg, 2.0 mmol) and 4-aminobutyric acid (190 mg, 2.1 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h.The reaction was quenched with water (10 mL), NaOH solution (0.1 mol/L)The pH of the solution was adjusted to 6-8. filter,After drying, it was 444 mg of a yellow solid.LC-MS and 1 H-NMR confirmed the expected intermediate compound, yield 95.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.5% | With acetic acid; at 100℃; for 3h; | 4-Isobutylphthalic anhydride (500 mg, 2.45 mmol) and 4-aminobutyric acid (260 mg, 2.5 mmol) were added to glacial acetic acid (10 mL), and the mixture was heated to 100 C for 3 h. The reaction was quenched with water (10 mL) and the NaOH solution (0.1 mol/L) was adjusted to pH 6-8. Dichloromethane extraction (10mL × 3), washed with saturated NaHCO3 solution, washed with water, combined with organic phase, dried over anhydrous sodium sulfateDry and dry, 640mg of yellow solid,LC-MS and 1 H-NMR confirmed the expected intermediate compound, yield 87.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91.2% | With acetic acid; at 100℃; for 3h; | 4-Alkyne phenyl phthalic anhydride (500 mg, 2.0 mmol) and 4-aminobutyric acid (206 mg, 2.0 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h.The reaction was quenched with water (10 mL) and the NaOH solution (0.1 mol/L) was adjusted to pH 6-8.Dichloromethane extraction (10mL × 3), washed with saturated NaHCO3 solution, washed with water,The organic phases were combined and dried over anhydrous sodium sulfate.After drying, 608 mg of a yellow solid was obtained.LC-MS and 1 H-NMR confirmed the expected intermediate compound in a yield of 91.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.6% | With acetic acid; at 100℃; for 3h; | 3,6-Difluorophthalic anhydride (368 mg, 2.0 mmol) and 4-aminobutyric acid (210 mg, 2.0 mmol) were added to glacial acetic acid (10 mL) and heated to 100 C for 3 h.The reaction was quenched with water (10 mL) and the NaOH solution (0.1 mol/L) was adjusted to pH 6-8.Dichloromethane extraction (10 mL × 3), washed with saturated NaHCO3 solution, washed with waterAfter drying, a yellow solid 365 mg was obtained.LC-MS and 1H-NMR confirmed the expected intermediate compound, yield72.6%. |