| Identification | Back Directory | [Name]
BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER | [CAS]
99548-55-7 | [Synonyms]
4-BROMO-2-METHYL-,METHYL ESTER
Methyl 2-methyl-4-bromobenzoate
4-BroMo-2-Methyl-benzoic acid Methyl ester
2- Methyl-4-broMo benzoic acidMethyl ester
BENZOIC ACID,4-BROMO-2-METHYL-,METHYL ESTER | [Molecular Formula]
C9H9BrO2 | [MDL Number]
MFCD09954957 | [MOL File]
99548-55-7.mol | [Molecular Weight]
229.07 |
| Chemical Properties | Back Directory | [Melting point ]
9 °C | [Boiling point ]
273.6±20.0 °C(Predicted) | [density ]
1.433±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [Appearance]
Colorless to light yellow Liquid | [InChI]
InChI=1S/C9H9BrO2/c1-6-5-7(10)3-4-8(6)9(11)12-2/h3-5H,1-2H3 | [InChIKey]
CYEXEOXALMJXDI-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(Br)C=C1C |
| Hazard Information | Back Directory | [Chemical Properties]
off-white powder | [Uses]
Methyl 4-Bromo-2-methylbenzoate can be used as an organic synthesis intermediate and a pharmaceutical intermediate. | [Synthesis]
Step 1: To a mixed solution of 4-bromo-2-methylbenzoic acid (15.1 g, 0.070 mol) in tetrahydrofuran (180 mL) and methanol (45 mL) was slowly added dropwise (trimethylsilyl) diazomethane in 2.0 M hexane solution (42 mL, 0.084 mol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to afford methyl 4-bromo-2-methylbenzoate (16 g, 100% yield) as a yellow oil. The crude product could be used in the subsequent reaction without further purification. The product was characterized as follows: 1H NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 7.42 (s, 1H), 7.38 (d, 1H), 3.88 (s, 3H), 2.58 (s, 3H). Mass spectrum (EI): m/z 230 ([M+H]+, C9H9BrO2). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 4, p. 999 - 1004
[2] Patent: WO2009/55077, 2009, A1. Location in patent: Page/Page column 430
[3] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2334 - 2356
[4] Patent: US2009/69370, 2009, A1. Location in patent: Page/Page column 17-18
[5] Patent: WO2009/158369, 2009, A1. Location in patent: Page/Page column 38; 39 |
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