2,6-DIBROMOBENZALDEHYDE Chemical Properties

Melting point:

92-93℃

Boiling point:

279℃

Density 

1.977

Flash point:

109℃

storage temp. 

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

form 

powder to crystal

color 

White to Yellow to Green

InChI

InChI=1S/C7H4Br2O/c8-6-2-1-3-7(9)5(6)4-10/h1-4H

InChIKey

YDYNSAUGVGAOLO-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2913000090

2,6-DIBROMOBENZALDEHYDE Usage And Synthesis

Chemical Properties

Off-white crystalline powder

Uses

2,6-Dibromobenzaldehyde is an important organic synthesis intermediate and can be used to synthesize a variety of other organic compounds, such as 2,6-dibromobenzoic acid, 2,6-dibromophenethanol, etc.

Synthesis

To a tetrahydrofuran (THF, 180 mL) solution of diisopropylamine (iPr2NH, 21.2 mL, 150 mmol) was slowly added n-butyllithium (n-BuLi, 1.6 M, 94 mL, 150 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 30 min and then cooled to -78 °C. Subsequently, a solution of 1,3-dibromobenzene (17.6 g, 74.6 mmol) in THF (80 mL) was slowly added over 20 min. The mixture was continued to be stirred at -78 °C for 30 min and then N,N-dimethylformamide (DMF, 11.6 mL, 150 mmol) was added. The reaction mixture was stirred at -78 °C for 1 h. The reaction was quenched with 2.5 M sulfuric acid (H2SO4, 350 mL) and extracted with a solvent mixture of ethyl acetate/ether (50/50, 3 x 300 mL). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and the filtrate was concentrated to give 2,6-dibromobenzaldehyde (17.6 g, 89% yield). The product was characterized by 1H NMR (250 MHz, CDCl3): δ 10.3 (s, 1H), 7.65 (d, J = 8.0 Hz, 2H), 7.23 (t, J = 8.1 Hz, 1H).

References

[1] Chemical Communications, 2015, vol. 51, # 35, p. 7486 - 7488
[2] Patent: US2016/95858, 2016, A1. Location in patent: Paragraph 2877; 2878
[3] Patent: US2018/72753, 2018, A1. Location in patent: Paragraph 0106-0107
[4] Organic Process Research and Development, 2014, vol. 18, # 1, p. 228 - 238
[5] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5384 - 5387

2,6-DIBROMOBENZALDEHYDE(67713-23-9)Related Product Information

• 3-HYDROXY-2,4,6-TRIBROMOBENZALDEHYDE
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• 2,4,6-TRIBROMOBENZOIC ACID
• 3-Hydroxy-2,4,6-tribromobenzoic acid
• METHYL 2,6-DIBROMOBENZOATE
• TETRABROMOTEREPHTHALIC ACID
• 2,6-dibromo-4-methylbenzaldehyde
• GADOMELITOL
• 3-HYDROXY-2,4,6-TRIBROMOBENZOIC ACID MONOHYDRATE
• 2,6-DIBROMOBENZOIC ACID
• 2,6-DIBROMOBENZALDEHYDE
• 3-AMINO-2,4,6-TRIBROMOBENZOIC ACID
• 2,6-Dibromo-3,5-Dimethylbenzoic Acid
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• RARECHEM AL BF 1488
• AKOS B028925
• RARECHEM AL BI 1488