| Identification | Back Directory | [Name]
METHYL 2-(2-BROMOPHENYL)ACETATE | [CAS]
57486-69-8 | [Synonyms]
2-broMobenzyl acetate
Methyl 2-(2-bromophenyl)
Methyl o-bromophenylacetate
Methyl 2-bromophenylacetate
(2-BroMophenyl)Methyl acetate
METHYL 2-(2-BROMOPHENYL)ACETATE
Methyl 2-bromophenylacetate 98%
Methyl 2-(2-bromophenyl)acetate 98%
2-Bromobenzeneacetic acid methyl ester
Benzeneacetic acid,2-bromo-, methyl ester
(2-BROMO-PHENYL)-ACETIC ACID METHYL ESTER | [Molecular Formula]
C9H9BrO2 | [MDL Number]
MFCD07779430 | [MOL File]
57486-69-8.mol | [Molecular Weight]
229.07 |
| Chemical Properties | Back Directory | [Boiling point ]
264℃ | [density ]
1.445 | [Fp ]
114℃ | [storage temp. ]
Keep Cold | [form ]
liquid | [color ]
Pale yellow | [InChI]
InChI=1S/C9H9BrO2/c1-12-9(11)6-7-4-2-3-5-8(7)10/h2-5H,6H2,1H3 | [InChIKey]
AMVCFIFDMKEIRE-UHFFFAOYSA-N | [SMILES]
C1(CC(OC)=O)=CC=CC=C1Br |
| Hazard Information | Back Directory | [Uses]
Methyl 2-(2-bromophenyl)acetate is a reagent in the synthesis of 2,3,3a,12b-Tetradehydro Asenapine (T291630). 2,3,3a,12b-Tetradehydro Asenapine is a degredation product of Asenapine (A788000), a combined serotonin (5HT2) and dopamine (D2) receptor antagonist; structurally related to Mianserin. Antipsychotic. | [Synthesis]
General method: o-Bromophenylacetic acid (5.0 g, 18.18 mmol) was dissolved in methanol (50 mL) containing a catalytic amount of concentrated sulfuric acid and the reaction was refluxed for 30 minutes. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated under reduced pressure to remove the solvent. Water (30 mL) was added to the residue, which was subsequently extracted with dichloromethane (3 x 20 mL). The organic layers were combined, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the corresponding methyl 2-(2-bromophenyl)acetate products. The products were: methyl 2-(2-bromo-4,5-dimethoxyphenyl)acetate (S5a, 5.19 g, 99%, brown oil); methyl 2-(2-bromo-5-methoxyphenyl)acetate (S5b, 2.09 g, 99%, brown oil); methyl 2-(2-bromo-4-methoxyphenyl)acetate (S5c, 2.09 g, 99%, brown oil ); methyl 2-(2-bromophenyl)acetate (S5d, 5.27g, 99%, clear oil). | [References]
[1] Journal of the American Chemical Society, 2003, vol. 125, # 11, p. 3268 - 3272
[2] Chemistry - An Asian Journal, 2011, vol. 6, # 8, p. 2040 - 2047
[3] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920
[4] Chemistry - A European Journal, 2016, vol. 22, # 34, p. 12166 - 12175
[5] Tetrahedron Letters, 2003, vol. 44, # 2, p. 331 - 334 |
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