| Identification | More | [Name]
2-BROMO-5-HYDROXYBENZALDEHYDE | [CAS]
2973-80-0 | [Synonyms]
2-BROMO-5-HYDROXYBENZALDEHYDE
4-BROMO-3-FORMYLPHENOL
AKOS B020430
ART-CHEM-BB B020430 | [Molecular Formula]
C7H5BrO2 | [MDL Number]
MFCD03033065 | [Molecular Weight]
201.02 | [MOL File]
2973-80-0.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 3077 | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
2909500090 |
| Hazard Information | Back Directory | [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.
| [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 |
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