2-Bromo-3-hydroxybenzaldehyde Chemical Properties

Melting point:

147-148℃

Boiling point:

252℃

Density 

1.737

Flash point:

106℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

7.71±0.10(Predicted)

color 

Off-White to Pale Beige

InChI

InChI=1S/C7H5BrO2/c8-7-5(4-9)2-1-3-6(7)10/h1-4,10H

InChIKey

OHXPHMPERMIICA-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=CC(O)=C1Br

Safety Information

Hazard Codes 

Xi

HS Code 

2913000090

2-Bromo-3-hydroxybenzaldehyde Usage And Synthesis

Chemical Properties

Yellow Solid

Uses

2-Bromo-3-hydroxybenzaldehyde is a reactant used in the preparation of a class of benzoxaboroles antimalarial agents.

Synthesis

The general procedure for the synthesis of 2-bromo-3-hydroxybenzaldehyde from m-hydroxybenzaldehyde was as follows: 3-hydroxybenzaldehyde (5 g, 0.04 mol), iron powder (172 mg, 3 mmol), and sodium acetate (6.72 g, 0.08 mol) were suspended in acetic acid (40 mL), warmed until a clarified solution was formed, and subsequently cooled to room temperature. A glacial acetic acid solution of bromine (10 mL) was slowly added dropwise to the mixture over 15 minutes. After the dropwise addition was completed, stirring of the reaction mixture was continued for 2 hours. Upon completion of the reaction, the mixture was poured into ice water and extracted with dichloromethane (3 x 50 mL). The organic phases were combined, dried over anhydrous Na2SO4 and concentrated. The residue was recrystallized by dichloromethane to afford the target product 2-bromo-3-hydroxybenzaldehyde (2.3 g, 28% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 10.30 (s, 1H), 7.54-7.51 (m, 1H), 7.39-7.35 (m, 1H), 7.31-7.27 (m, 1H), 5.90 (s, 1H).

References

[1] European Journal of Organic Chemistry, 2007, # 34, p. 5726 - 5733
[2] Patent: WO2012/33858, 2012, A2. Location in patent: Page/Page column 76
[3] Patent: WO2015/21396, 2015, A2. Location in patent: Paragraph 00121-00122
[4] Organic Letters, 2016, vol. 18, # 21, p. 5656 - 5659

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