| Identification | Back Directory | [Name]
5-Bromoacetyl-2-hydroxybenzaldehyde | [CAS]
115787-50-3 | [Synonyms]
Salbutamol Impurity 18
Salbutamol Impurity 29
5-(Bromoacetyl)salicylaldehyde
5-Bromoacetyl-2-hydroxybenzaldehyde
Benzaldehyde,5-(2-broMoacetyl)-2-hydroxy-
5-Bromoacetyl-2-hydroxybenzaldehyde ISO 9001：2015 REACH
2- Bromo-1 - [4-hydroxy-3 - (hydroxymethyl) phenyl] pento-1-one | [EINECS(EC#)]
1308068-626-2 | [Molecular Formula]
C9H7BrO3 | [MDL Number]
MFCD09833486 | [MOL File]
115787-50-3.mol | [Molecular Weight]
243.054 |
| Chemical Properties | Back Directory | [Melting point ]
117-118 °C(Solv: dichloromethane (75-09-2)) | [Boiling point ]
368.3±32.0 °C(Predicted) | [density ]
1.685±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
5.93±0.20(Predicted) | [color ]
Yellow to Dark Yellow | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C9H7BrO3/c10-4-9(13)6-1-2-8(12)7(3-6)5-11/h1-3,5,12H,4H2 | [InChIKey]
LPSGRBXPXIPMPF-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC(C(CBr)=O)=CC=C1O |
| Hazard Information | Back Directory | [Chemical Properties]
Brown Solid | [Uses]
Intermediate in the preparation of Salmeterol (S090100). | [Synthesis]
To a suspension of aluminum chloride (4 mole equivalents) in dichloromethane (10 volumes), bromoacetyl bromide (1.2 mole equivalents) was added slowly and dropwise at 100 °C, and the temperature of the reaction system was subsequently adjusted to 30 °C. The reaction mixture was stirred continuously for 1 hour, and then 2-hydroxybenzaldehyde (1 mole equivalent) was added dropwise in dichloromethane. The reaction mixture was stirred continuously at this temperature for 1 h. Then a dichloromethane solution of 2-hydroxybenzaldehyde (1 mole equivalent) was added dropwise. The reaction mixture was stirred at 35-40 °C for 12-15 hours, followed by quenching the reaction with water at 0-50 °C. The organic layer (dichloromethane layer) was separated and the solvent was removed by distillation. To the residue n-heptane was added and stirred for 15 minutes. The resulting slurry was filtered and the wet filter cake was washed with n-heptane (2 vol). The wet filter cake was dried to constant weight at 50 °C to give the intermediate 5-bromoacetyl-2-hydroxybenzaldehyde (2a). Yield: 55% (w/w); HPLC purity: 97-99 | [References]
[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 13, p. 4194 - 4198
[2] Angew. Chem., 2016, vol. 128, # 13, p. 4266 - 4270,5
[3] Tetrahedron Asymmetry, 2008, vol. 19, # 15, p. 1824 - 1828
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1548 - 1552
[5] Chemical Communications, 2018, vol. 54, # 25, p. 3106 - 3109 |
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