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| | 2-BROMO-5-HYDROXYBENZALDEHYDE Basic information |
| | 2-BROMO-5-HYDROXYBENZALDEHYDE Chemical Properties |
| Melting point | 130-135 °C | | Boiling point | 286.7±20.0 °C(Predicted) | | density | 1.737±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,2-8°C | | solubility | Soluble in chloroform, dichloromethane and ethyl acetate. | | form | Solid | | pka | 8.67±0.18(Predicted) | | color | White to Gray to Brown | | InChI | InChI=1S/C7H5BrO2/c8-7-2-1-6(10)3-5(7)4-9/h1-4,10H | | InChIKey | SCRQAWQJSSKCFN-UHFFFAOYSA-N | | SMILES | C(=O)C1=CC(O)=CC=C1Br | | CAS DataBase Reference | 2973-80-0(CAS DataBase Reference) |
| Hazard Codes | Xi,N,Xn | | Risk Statements | 36/37/38-50-22 | | Safety Statements | 26-36/37/39-61 | | RIDADR | UN 3077 | | WGK Germany | 3 | | Hazard Note | Irritant | | HazardClass | 9 | | PackingGroup | III | | HS Code | 2909500090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Aquatic Acute 1 |
| | 2-BROMO-5-HYDROXYBENZALDEHYDE Usage And Synthesis |
| Chemical Properties | Pale Grey Solid | | Uses | 2-Bromo-5-hydroxybenzadehyde is a reactant used in the preparation of many pharmaceutical agents: Bcl-XL, PDE4 inhibitors, inhibitors of prostate cancer cell growth and anti-inflamatory agents. | | Uses | 2-Bromo-5-hydroxybenzaldehyde is a useful reactant used in the synthesis of PDE4 inhibitors, BCL-XL and cancel cell growth inhibitors. Also an reactant used in the preparation of many pharmaceutical agents. | | Synthesis | General procedure for the synthesis of 2-bromo-5-hydroxybenzaldehyde from m-hydroxybenzaldehyde: 3-hydroxybenzaldehyde (120 g, 0.98 mol) was suspended in 2400 mL of dichloromethane (CH2Cl2) in a 5 L four-necked, round-bottomed flask fitted with an overhead stirrer, a temperature probe, a dosing funnel, and a condenser tube. The mixture was heated to 35-40 °C to completely dissolve the raw material. Bromine (52 mL, 1.0 mol, 1.02 eq.) was added slowly dropwise through the addition funnel, controlling the rate of dropwise acceleration to maintain the reaction temperature between 35-38°C. After dropwise addition, the reaction mixture was stirred at 35 °C overnight. Subsequently, the mixture was slowly cooled to -5-0 °C over a period of 2 h and stirring was continued for 1 h at this temperature. The precipitated solid was collected by filtration through a Brinell funnel and the filter cake was washed with 400 mL of cold 1:1 n-heptane/dichloromethane mixture. The resulting gray solid was dried under vacuum at room temperature (0.2 mmHg). The yield was 124.3 g in 63% yield. | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 8, p. 955 - 959
[2] Patent: US2004/19018, 2004, A1. Location in patent: Page/Page column Sheet 2
[3] Journal of the Iranian Chemical Society, 2011, vol. 8, # 2, p. 531 - 536
[4] Tetrahedron Letters, 2009, vol. 50, # 9, p. 1007 - 1009
[5] Synthetic Communications, 2007, vol. 37, # 4, p. 581 - 585 |
| | 2-BROMO-5-HYDROXYBENZALDEHYDE Preparation Products And Raw materials |
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