METHYL 2-(2-BROMOPHENYL)ACETATE Chemical Properties

Boiling point:

264℃

Density 

1.445

Flash point:

114℃

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

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

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant/Keep Cold

HS Code 

2916399090

METHYL 2-(2-BROMOPHENYL)ACETATE Usage And Synthesis

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

METHYL 2-(2-BROMOPHENYL)ACETATE(57486-69-8)Related Product Information

• METHYL 2-(3-BROMOPHENYL)ACETATE
• METHYL ALPHA-BROMO-2-CHLOROPHENYLACETATE
• Ethyl 2-(2-bromophenyl)acetate
• METHYL 2-(2-BROMOPHENYL)ACETATE
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• METHYL ALPHA-BROMOPHENYLACETATE
• Methyl phenylacetate
• AMINO-(2-BROMO-PHENYL)-ACETIC ACID METHYL ESTER HYDROCHLORIDE
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• AKOS AU36-M258
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