2-Chloro-4-bromobenzaldehyde CAS 158435-41-7
2-Chloro-4-bromobenzaldehyde Basic information
| Product Name: | 2-Chloro-4-bromobenzaldehyde |
| Synonyms: | 4-BROMO-2-CHLOROBENZALDEHYDE;2-Chloro-4-bromobenzaldehyde;Chloro-4-bromobenzaldehyde;Benzaldehyde,4-broMo-2-chloro-;2-Chloro-4-broMobenzaldehyde, 95+%;4-Bromo-2-chlorobenzaldehyde >2-Chloro-4-bromobenzaldehyde, 97%min |
| CAS: | 158435-41-7 |
| MF: | C7H4BrClO |
| MW: | 219.46 |
| EINECS: | |
| Product Categories: | Adehydes, Acetals & Ketones;Bromine Compounds;Chlorine Compounds |
| Mol File: | 158435-41-7.mol |
2-Chloro-4-bromobenzaldehyde Chemical Properties
| Melting point | 74-76℃ |
| Boiling point | 271.3±25.0 °C(Predicted) |
| density | 1.698±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,2-8°C |
| solubility | soluble in Methanol |
| form | powder to crystal |
| color | White to Orange to Green |
| Sensitive | Air Sensitive |
| CAS DataBase Reference | 158435-41-7(CAS DataBase Reference) |
Safety Information
| Hazard Codes | C,Xn |
| Risk Statements | 22 |
| Hazard Note | Corrosive |
| HS Code | 2913000090 |
| Chemical Properties | Light yellow crystalline powder |
| Uses | 4-Bromo-2-chlorobenzaldehyde is a useful research chemical for organic synthesis and other chemical processes.4-Bromo-2-chlorobenzaldehyde is used in preparation of Heterocyclic compounds as P2X3 antagonist and its intermediate. |
| Synthesis | 185315-48-4 158435-41-7 General procedure for the synthesis of 2-chloro-4-bromobenzaldehyde from (4-bromo-2-chlorophenyl)methanol: Oxalyl chloride (6.9 g, 54 mmol, 1.3 eq.) was dissolved in dichloromethane (DCM, 153 mL) and the solution was cooled to -78 °C. A solution of DCM (57 mL) in dimethyl sulfoxide (DMSO, 4.72 mL, 66.5 mmol, 1.6 eq.) was slowly added dropwise to the cooled solution at -78 °C and stirred for 15 min. (4-Bromo-2-chlorophenyl)methanol (Compound 43, 9.2 g, 41.5 mmol, 1.0 eq.) was dissolved in DCM (116 mL) and added drop-wise to the above cooled solution, keeping the temperature at -78 °C. Stirring was continued at -78 °C for 2 hours. Subsequently, triethylamine (TEA, 28.7 mL, 207 mmol, 5 eq.) was added to slowly warm the reaction mixture to room temperature. After stirring for 30 min at room temperature, the reaction mixture was diluted with DCM (300 mL), washed sequentially with saturated ammonium chloride (NH4Cl) solution and brine, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated in vacuum to afford 2-chloro-4-bromobenzaldehyde (Compound 44) in 96% yield (8.8 g). |
| References | [1] Patent: WO2008/51826, 2008, A2. Location in patent: Page/Page column 53; 54 [2] Patent: WO2008/103277, 2008, A2. Location in patent: Page/Page column 197 [3] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7820 - 7834 [4] Patent: WO2013/75083, 2013, A1. Location in patent: Paragraph 006309; 00632 [5] Patent: US9206128, 2015, B2. Location in patent: Page/Page column 275; 276; 277 |
2-Chloro-4-bromobenzaldehyde Preparation Products And Raw materials
| Raw materials | 2-Chlorobenzaldehyde-->Benzene, 4-bromo-2-chloro-1-(dibromomethyl)--->(4-Bromo-2-chlorophenyl)methanol-->Benzamide, 4-bromo-2-chloro-N-methoxy-N-methyl--->4-BROMO-2-CHLORO-1-IODOBENZENE-->N,N-Dimethylformamide-->Oxalyl chloride-->Dichloromethane-->Dimethyl sulfoxide-->Triethylamine |
| Preparation Products | 4-BROMO-1-BROMOMETHYL-2-CHLORO-BENZENE-->2-Chloro-4-bromoacetophenone-->Methyl 3-chloro-4-forMylbenzoate |
