| Identification | More | [Name]
Methyl 2,5-dibromobenzoate | [CAS]
57381-43-8 | [Synonyms]
2,5-DIBROMOBENZOIC ACID METHYL ESTER
3,4-DIAMINOBENZOIC ACID METHYL ESTER
METHYL 2,5-DIBROMOBENZOATE
2,5-DIBROMOBENZOIC ACID METHYL ESTER 98+% | [Molecular Formula]
C8H6Br2O2 | [MDL Number]
MFCD00144757 | [Molecular Weight]
293.94 | [MOL File]
57381-43-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
48-51 °C (lit.) | [Boiling point ]
291.3±20.0 °C(Predicted) | [density ]
1.840±0.06 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Orange to Green | [Water Solubility ]
Slightly soluble in water. | [CAS DataBase Reference]
57381-43-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [TSCA ]
N | [HS Code ]
2916399090 |
| Hazard Information | Back Directory | [General Description]
Methyl 2,5-dibromobenzoate, an aromatic ester, can be prepared from 2,5-dibromobenzoic acid via esterification with methanol. It undergoes Ni(0)-catalyzed polymerization to form soluble polyphenylenes. | [Synthesis]
Step 1: A methanol (2L) solution of 2,5-dibromobenzoic acid (250 g, 0.90 mol) and concentrated sulfuric acid (18.4 g, 0.19 mol) were added to a 2L round bottom flask. The reaction mixture was heated to reflux overnight and subsequently cooled to room temperature. The resulting precipitate was collected by filtration, washed with cold methanol and dried under vacuum to give 203.6 g of methyl 2,5-dibromobenzoate as a yellow solid. Step 2: To another 2L round-bottomed flask was added a solution of methyl 2,5-dibromobenzoate (198.2 g, 0.68 mol) in anhydrous DMF (1L). Copper cyanide (122 g, 1.36 mol) and sodium iodide (22.8 g, 0.15 mol) were subsequently added. The mixture was stirred at 130 °C overnight under nitrogen protection. Upon completion of the reaction, extraction was carried out with ethyl acetate (500 mL x 3), the organic layer was washed with water (500 mL), and finally purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5/1) to afford 95.2 g of methyl 2,5-dicyanobenzoate as a brown solid in 75.1% yield. | [References]
[1] Tetrahedron, 2016, vol. 72, # 24, p. 3454 - 3467
[2] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6655 - 6657 |
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