| Identification | Back Directory | [Name]
Methyl 3-bromo-5-nitrobenzoate | [CAS]
6307-87-5 | [Synonyms]
Methyl 3-bromo-5-nitrobenzoate
Methyl3-bromo-5-nitrobenzoate98%
Methyl 3-bromo-5-nitrobenzoate 98%
3-Bromo-5-nitro-benzoic acid methyl ester
Benzoic acid, 3-bromo-5-nitro-, methyl ester | [Molecular Formula]
C8H6BrNO4 | [MDL Number]
MFCD09258759 | [MOL File]
6307-87-5.mol | [Molecular Weight]
260.042 |
| Chemical Properties | Back Directory | [Melting point ]
70 °C(Solv: ethanol (64-17-5)) | [Boiling point ]
326.0±22.0 °C(Predicted) | [density ]
1.673±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
solid | [color ]
Off-white to light brown | [InChI]
InChI=1S/C8H6BrNO4/c1-14-8(11)5-2-6(9)4-7(3-5)10(12)13/h2-4H,1H3 | [InChIKey]
DDJCZBFPZLYREP-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC([N+]([O-])=O)=CC(Br)=C1 |
| Hazard Information | Back Directory | [Uses]
Methyl 3-bromo-5-nitrobenzoate is a pharmaceutical intermediate. Methyl 3-bromo-5-nitrobenzoate can be used to prepare 3-amidobenzoic acid derivatives such as 3-(4-trifluoromethylbenzoyl)amino-5-(2',6'-(2H)piperidinylphenyl)benzoic acid, which have P2Y receptor antagonist effects. | [Synthesis]
The preparation method is achieved through a two-step reaction: first, at 0°C, 3-nitrobenzoic acid is dissolved in concentrated sulfuric acid, N-bromosuccinimide is added, the reaction is carried out at 65°C for 2 hours, and 3-nitro-5-bromobenzoic acid is obtained after stirring with ice water, suction filtration, and drying, with a yield of 95%. Next, the product is dissolved in methanol, SOCl₂ is added dropwise at 0°C, the reaction is carried out at room temperature for 2 hours, and Methyl 3-bromo-5-nitrobenzoate is finally obtained after treatment with a sodium bicarbonate solution, extraction with ethyl acetate, drying, and column chromatography purification, with a yield of 86.46%. | [References]
[1] Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4764 - 4774
[2] Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17408 - 17416
[3] Patent: WO2014/19685, 2014, A1. Location in patent: Page/Page column 13; 39
[4] Journal of Molecular Structure, 2013, vol. 1036, p. 505 - 509
[5] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3496 - 3505 |
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