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Chemical Structure| 4841-23-0 Chemical Structure| 4841-23-0

Structure of 4841-23-0

Chemical Structure| 4841-23-0

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Product Details of [ 4841-23-0 ]

CAS No. :4841-23-0
Formula : C9H9BrO3
M.W : 245.07
SMILES Code : O=C(OC)COC1=CC=C(Br)C=C1
MDL No. :MFCD01124700
InChI Key :UDAVOUGCAYAMAU-UHFFFAOYSA-N
Pubchem ID :700580

Safety of [ 4841-23-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 4841-23-0 ]

* 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.

  • Downstream synthetic route of [ 4841-23-0 ]

[ 4841-23-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 67-56-1 ]
  • [ 1878-91-7 ]
  • [ 4841-23-0 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; at 20℃; for 20h;Inert atmosphere; 2-(4-Bromophenoxy)-acetic acid 16 (1.0 g, 4.3 mmol) was added to a 3 M methanolic solution of hydrochloride (3 mL). The mixture was stirred for 20 h at room temperature under inert atmosphere. The solvent was removed under reduced pressure and the residual oil was dissolved in dichloromethane (15 mL) and was washed successively with water (10 mL), a saturated bicarbonate solution (10 mL) and then again with water (10 mL). The organic phase was dried over magnesium sulfate, filtered and then concentrated under reduced pressure to give compound 17a in the form of a colorless oil, which was sufficiently pure to be used in the rest of the synthesis without additional purification (1 g, 95%). 1H NMR (400 MHz, CDCl3) delta: 7.31 (d, J=8.5 Hz, 2H), 6.78 (d, J=8.5 Hz, 2H), 4.55 (s, 2H), 3.80 (s, 3H); 13C NMR (176 MHz, CDCl3) delta: 169.3, 157.1, 132.7, 116.7, 114.3, 65.6, 52.6; HRMS (ESI+) calculated for C9H9O3BrNa [M+Na]+, m/z 266.9633. found: 266.9622; Rf=0.65 (silica; cyclohexane-ethyl acetate 1:1).
  • 2
  • [ 4841-23-0 ]
  • [ 1878-91-7 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide monohydrate; In methanol; water; for 2h;Reflux; General procedure: To a stirred solution of methyl ester (2a-i, 1 mmol) in MeOH-H2O (3 : 1, 4 mL) was added LiOH?H2O (2 mmol), and the resulting mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure, the residue was acidified with 10% HCl aq. The aqueous mixture was extracted with EtOAc (5 mL x 6), and the organic extracts were combined, dried over Na2SO4, and evaporated to give the carboxylic acid. To a stirred solution of amide (3a-n, 3' and 3'', 1 mmol) in CH2Cl2 (5 mL) was added TFA (8 mmol), and the reaction mixture was stirred at room temperature for 24 h. The reaction was quenched with satd. NaHCO2 aq., and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (5 mL x 10), and the organic layer and extracts were combined, dried over K2CO3, and evaporated to give the amine. To a stirred solution of the carboxylic acid prepared above in CH2Cl2 (5 mL) was added CDI (1 mmol), and the reaction mixture was stirred at room temperature for 1 h. To the mixture was added a solution of the amine prepared above in CH2Cl2 (2 mL), and the resulting solution was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (15 g, hexane : acetone = 5 : 1 ~ 3 : 1) to give substituted acetamide.
 

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