| Identification | More | [Name]
2,3-Dibromofuran-5-carboxylic acid | [CAS]
2434-03-9 | [Synonyms]
2,3-DIBROMOFURAN-5-CARBOXYLIC ACID
4,5-DIBROMO-2-FUROIC ACID
4,5-Dibromo-2-furoicacid,97%
4,5-dibromofuran-2-carboxylic acid
4,5-Dibromo-2-furancarboxylic acid | [Molecular Formula]
C5H2Br2O3 | [MDL Number]
MFCD00092311 | [Molecular Weight]
269.88 | [MOL File]
2434-03-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
169-173 °C | [Boiling point ]
328.7±42.0 °C(Predicted) | [density ]
2.304±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
solid | [pka]
2.58±0.16(Predicted) | [Appearance]
White to off-white Solid | [BRN ]
129312 | [InChI]
InChI=1S/C5H2Br2O3/c6-2-1-3(5(8)9)10-4(2)7/h1H,(H,8,9) | [InChIKey]
BHUVICYZDBUMIU-UHFFFAOYSA-N | [SMILES]
O1C(Br)=C(Br)C=C1C(O)=O | [CAS DataBase Reference]
2434-03-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
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
| [HS Code ]
2932190090 |
| Hazard Information | Back Directory | [Uses]
Used in a study of the effect of a furanyl halo-substituent on the intramolecular Diels-Alder reaction between the furan ring system and a pendant allylamide. The yield of the cycloaddition is improved with a C-5 bromide vs -chloro or -unsubstituted furan. | [Uses]
2,3-Dibromofuran-5-carboxylic acid is used in a study of the effect of a furanyl halo-substituent on the intramolecular Diels-Alder reaction between the furan ring system and a pendant allylamide. The yield of the cycloaddition is improved with a C-5 bromide vs -chloro or -unsubstituted furan.
| [Synthesis]
Step B: Synthesis of 4,5-dibromo-2-furoic acid. Methyl 4,5-dibromofuran-2-carboxylate (26.19 g, 92.2 mmol) was suspended in THF (60 mL) followed by addition of LiOH (3 M aqueous solution, 60 mL, 180 mmol). The resulting two-phase mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the mixture was slowly poured into 1 N HCl solution and extracted with dichloromethane (DCM, 4 x 60 mL). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 24.59 g (99% yield) of the target product 4,5-dibromo-2-furoic acid as an off-white solid. The product was characterized by 1H NMR (CD3OD): δ 7.30 (s, 1H). | [References]
[1] Patent: WO2008/124518, 2008, A1. Location in patent: Page/Page column 18
[2] Patent: US2006/69286, 2006, A1. Location in patent: Page/Page column 25
[3] Chemical and Pharmaceutical Bulletin, 1997, vol. 45, # 5, p. 799 - 806
[4] European Journal of Organic Chemistry, 1999, # 9, p. 2045 - 2057 |
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Sigma-Aldrich
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