2,3-Dibromofuran-5-carboxylic acid Chemical Properties

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 Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2932190090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,3-Dibromofuran-5-carboxylic acid Usage And Synthesis

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

2,3-Dibromofuran-5-carboxylic acid(2434-03-9)Related Product Information

• 2-Furoic acid
• EPA
• ACETONE-D6
• 1,3-Dibromo-5,5-dimethylhydantoin
• Mometasone furoate
• (R)-(+)-2-Tetrahydrofuroic acid
• Ascoric Acid
• 3-Bromofuran
• 2,3-DIBROMOFURAN
• 5-Bromofuroic acid
• 2-Bromofuran
• 5-Bromo-2-furaldehyde
• 4-Bromo-2-furaldehyde
• 4,5-Dibromo-2-furaldehyde
• Methyl-4,5-dibromo-2-furoate
• 2,3-Dibromofuran-5-carboxylic acid
• CARBOXYLIC ACID