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| | 5-Bromoacetyl-2-hydroxybenzaldehyde Basic information |
| Product Name: | 5-Bromoacetyl-2-hydroxybenzaldehyde | | Synonyms: | 5-Bromoacetyl-2-hydroxybenzaldehyde;Salbutamol Impurity 18;Salbutamol Impurity 29;5-(Bromoacetyl)salicylaldehyde;Benzaldehyde,5-(2-broMoacetyl)-2-hydroxy-;2- Bromo-1 - [4-hydroxy-3 - (hydroxymethyl) phenyl] pento-1-one;5-Bromoacetyl-2-hydroxybenzaldehyde ISO 9001：2015 REACH;5-bromoacetyl-3-hydroxybenzaldehyde | | CAS: | 115787-50-3 | | MF: | C9H7BrO3 | | MW: | 243.05 | | EINECS: | 1308068-626-2 | | Product Categories: | Intermediate;115787-50-3 | | Mol File: | 115787-50-3.mol |  |
| | 5-Bromoacetyl-2-hydroxybenzaldehyde Chemical Properties |
| 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. | under inert gas (nitrogen or Argon) at 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 |
| | 5-Bromoacetyl-2-hydroxybenzaldehyde Usage And Synthesis |
| 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 |
| | 5-Bromoacetyl-2-hydroxybenzaldehyde Preparation Products And Raw materials |
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