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CAS No. : | 16503-53-0 | MDL No. : | MFCD00461796 |
Formula : | C9H9BrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WDRSCFNERFONKU-UHFFFAOYSA-N |
M.W : | 229.07 | Pubchem ID : | 167544 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
With thionyl chloride; | EXAMPLE III 60.5g of 2-bromo-3-phenylpropionic acid was mixed with 100 ml of thionylchloride and the mixture was refluxed for 3 hours and, after the excess thionylchloride had been distilled off, was distilled under reduced pressure to give 46.2g of 2-bromo-3-phenylpropionylchloride. (b.p. 100- 101C/4 mmHg) | |
With oxalyl dichloride;N,N-dimethyl-formamide; In chloroform; at 1 - 40℃; | step 2 Production of 2-bromo-3-phenylpropionylchloride 2-Bromo-3-phenylpropionic acid (6.0 g) was dissolved in chloroform (25 mL), and oxalyl chloride (2.97 mL) and N,N-dimethylformamide (one drop) were added. After stirring the mixture overnight at room temperature, the mixture was concentrated and azeotroped with toluene to give the title compound as a yellow oil. | |
With thionyl chloride; for 2h;Reflux; | General procedure: A flask was charged with2-bromohexanoic acid (1.95 g, 10 mmol) at 0 C and thionyl chloride (10 mL) was added dropwise. The mixture was stirred at rt for 10 min and then heated under reflux for 2 h. The excess thionylchloride was removed by distillation and the resulting acyl chloride was used without any further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With perchloric acid; at 0 - 20℃; | tert-Butyl 2-bromo-3-phenylpropionate; A mixture of 10.1 g (44.1 mmol) of 2-bromo-3-phenylpropionic acid in tert-butyl acetate (150 ml) was cooled in an ice/water bath. 0.5 ml of perchloric acid was <n="65"/>added, and the reaction solution was stirred at room temperature overnight. The reaction solution was slowly added to a saturated aqueous sodium bicarbonate solution (200 ml) and the organic phase was separated off. The aqueous phase was extracted twice with 60 ml of ethyl acetate each time, the combined organic phases were washed with saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 20% acetic acid in cyclohexane). Yield: 6.76 g (54%) of colorless oil1H-NMR (CDCI3): 1.40 (s, 9H), 3.20 (dd, 14.0 Hz, 6.9 Hz, 1 H), 3.41 (dd, 14.0 Hz, 8.7 Hz, 1 H), 4.30 (dd, 8.7 Hz, 6.9 Hz, 1 H), 7.18-7.34 (m, 5H). MS (API-ES,pos) m/z = 307, 309 [M+Na]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; diisopropyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 2 - 16h; | Example 1252-(4-Hydroxybenzenesulfanyl)-N-hydroxy-3-phenyl-propionamide Step A: Coupling of <strong>[16503-53-0]2-bromo-3-phenyl-propionic acid</strong> to hydroxylamine resin. 4-O-Methylhydroxylamine-phenoxymethyl-copoly(styrene-1%-divinylbenzene)-resin1 (5 g, 1.2 meq/g) was placed in a peptide synthesis vessel and suspended in DMF (40 mL). 2-Bromo-3-phenyl-propionic acid (3.5 g, 3.0 eq.) HOBt (4.4 g, 6.0 eq.) and DIC (3.4 mL, 4.0 eq.) were added. The reaction was shaken on an orbital shaker at room temperature for 2 - 16 hours. The reaction was filtered and washed with DMF (3 x 20 mL). A sample of resin was removed and subjected to the Kaiser test. If the test showed the presence of free amine (resin turned blue) the coupling described above was repeated, otherwise the resin was washed with DCM (3 x 20 mL), MeOH (2 x 20 mL), and DCM (2 x 20 mL). The resin was dried in vacuo at room temperature. | |
With benzotriazol-1-ol; diisopropyl-carbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; | 4-O-Methylhydroxylamine-phenoxymethyl-copoly(styrene-1%-divinylbenzene)-resin1 (5 g, 1.2 meq/g) was placed in a peptide synthesis vessel and suspended in DMF (40 mL). 2-Bromo-3-phenyl-propionic acid (3.5 g, 3.0 eq.) HOBt (4.4 g, 6.0 eq.) and DIC (3.4 mL, 4.10 eq.) were added. The reaction was shaken on an orbital shaker at room temperature for 2-16 hours. The reaction was filtered and washed with DMF (320 mL). A sample of resin was removed and subjected to the Kaiser test. If the test showed the presence of free amine (resin turned blue) the coupling described above was repeated, otherwise the resin was washed with DCM (320 mL), MeOH (220 mL), and DCM (220 mL). The resin was dried in vacuo at room temperature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In benzene; | EXAMPLE 4 The reaction was conducted in the same manner as in Example 1 except that in example 1, 10.50 g (50 mmol) of α-bromo-β-phenylpropionitrile was used instead of α-chloro-β-phenylpropionitrile. After the completion of the reaction, the organic phase and the aqueous phase were separated. To the organic phase, 50 ml of benzene was added, and then organic phase was washed twice with 30 ml of a saturated sodium chloride aqueous solution. The benzene phase was dried over anhydrous sodium sulfate, and then benzene was distilled off, whereby 10.2 g (yield: 89%) of α-bromo-β-phenylpropionic acid was obtained as oily substance. |
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