2-Bromo-6-hydroxybenzaldehyde
2-Bromo-6-hydroxybenzaldehyd · 6-Bromosalicylaldehyde · 3-BroMo-2-forMylphenol · 2-bromo-hydroxybenzaldehyde · 2-Bromo-6-hydroxybenzaldehyde · 6-bromo-2-hydroxybenzaldehyde · 2-hydroxy-6-bromobenzaldehyde · Benzaldehyde,2-broMo-6-hydroxy-
Identifiers & Physical Properties
| CAS No. | 22532-61-2 |
|---|---|
| Molecular formula | C7H5BrO2 |
| Average molar mass | 201.02 g/mol |
| Monoisotopic mass | 199.94729 g/mol |
| SMILES | O=Cc1c(O)cccc1Br |
| InChIKey | LQTXMBDCLHZDAM-UHFFFAOYSA-N |
| PubChem CID | 11954768 |
| EC No. | 696-195-0 |
| DTXSID | DTXSID30474659 |
Chemical & Physical Properties
| XLogP | 2.3 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 127 |
| Melting point | 50-52 °C |
| Boiling point | 243.4±20.0 °C(Predicted) |
| Density | 1.737±0.06 g/cm3(Predicted) |
| Storage conditions | under inert gas (nitrogen or Argon) at 2-8°C |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Physical state | Solid |
| pKa (acidity coefficient) | 7.21±0.10(Predicted) |
| Color | Light Yellow |
| InChI | InChI=1S/C7H5BrO2/c8-6-2-1-3-7(10)5(6)4-9/h1-4,10H |
| InChIKey | LQTXMBDCLHZDAM-UHFFFAOYSA-N |
| SMILES | C(=O)C1=C(O)C=CC=C1Br |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
| Customs code | 2912210000 |
Safety & Regulations
| GHS classification | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (66.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute Tox. 4 (66.7%)Skin Irrit. 2 (33.3%)Eye Irrit. 2 (33.3%)STOT SE 3 (33.3%) |
| Customs code | 2912210000 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| GHS hazard statements | H302-H315-H319-H332-H335 |
| GHS precautionary statements | P261-P280-P305+P351+P338 |
Applications & Uses
Uses
2-Bromo-6-hydroxybenzaldehyde, is a substituted salicylaldehyde used in the synthesis of BIIB042, a γ-secretase modulator.
Preparation & Synthesis
Preparation
Step a: 2,6-Dibromobenzaldehyde, toluene, 1,3-propanediol, and concentrated sulfuric acid are heated to reflux and water is removed. After the reaction is complete, the mixture is cooled to room temperature, neutralized with sodium methoxide, and distilled under reduced pressure to obtain intermediate a;Step b: Intermediate a and tetrahydrofuran are cooled to -10℃ to 5℃, isopropyl Grignard reagent is added, Grignard exchange is completed, then trialkyl borate is added and the reaction is maintained at this temperature; hydrochloric acid is used to quench the reaction, organic solvent is used for extraction and separation, and the mixture is evaporated to dryness to obtain intermediate b;Step c: Intermediate b is added to an alcohol/water mixed solvent and a copper catalyst, and hydrogen peroxide is added for reaction; sodium thiosulfate solution is used to quench the reaction, extraction and separation are performed, organic solvent is added for slurrying, and filtration is used to obtain 2-bromo-6-hydroxybenzaldehyde.