| Identification | Back Directory | [Name]
2,6-DIBROMOBENZALDEHYDE | [CAS]
67713-23-9 | [Synonyms]
2,6-DIBROMOBENZALDEHYDE
Benzaldehyde, 2,6-dibroMo-
2,6-Dibromobenzaldehyde 95%
1,3-Dibromo-2-formylbenzene
2,6-Dibromobenzaldehyde >
2,6-Dibromobenzenecarbaldehyde
2,6-Dibromobenzaldehyde≥ 98% (GC) | [Molecular Formula]
C7H4Br2O | [MDL Number]
MFCD11040410 | [MOL File]
67713-23-9.mol | [Molecular Weight]
263.93 |
| Chemical Properties | Back Directory | [Melting point ]
92-93℃ | [Boiling point ]
279℃ | [density ]
1.977 | [Fp ]
109℃ | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
|
|