2-Bromo-5-fluorobenzaldehyde CAS 94569-84-3
2-Bromo-5-fluorobenzaldehyde Basic information
| Product Name: | 2-Bromo-5-fluorobenzaldehyde |
| Synonyms: | 2-Bromo-5-fluorobenzaldehyde 96%;2-BROMO-5-FLUOROBENZALDEHYDE;5-Fluoro-2-Bromo benzaldehyde;2-BROMO-5-FLUOROBENZALDHYDE;2-Bromo-5-fluorobenzaldehyde ,98%;2-BroMo-5-fluorobenzaldehyde, 95+%;Benzaldehyde, 2-broMo-5-fluoro-;2-Bromo-5-fluorobenzaldehyde > |
| CAS: | 94569-84-3 |
| MF: | C7H4BrFO |
| MW: | 203.01 |
| EINECS: | 619-047-9 |
| Product Categories: | Ipragliflozin;Aryl Fluorinated Building Blocks;Building Blocks;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Aromatic Aldehydes & Derivatives (substituted);Furans, Benzofurans & Dihydrobenzofurans;Phenyls & Phenyl-Het;Benzaldehyde;API intermediates;Benzaldehyde series;Aldehydes;blocks;FluoroCompounds;Carbonyl Compounds;Adehydes, Acetals & Ketones;Bromine Compounds;Fluorine Compounds;Phenyls & Phenyl-Het;Furans, Benzofurans & Dihydrobenzofurans;C7;Carbonyl Compounds |
| Mol File: | 94569-84-3.mol |
2-Bromo-5-fluorobenzaldehyde Chemical Properties
| Melting point | 51-56 °C (lit.) |
| Boiling point | 225.8±20.0 °C(Predicted) |
| density | 1.670±0.06 g/cm3(Predicted) |
| Fp | 190 °F |
| storage temp. | 2-8°C |
| solubility | Soluble in methanol. |
| form | powder to lump |
| color | White to Orange to Green |
| Sensitive | Air Sensitive |
| InChI | InChI=1S/C7H4BrFO/c8-7-2-1-6(9)3-5(7)4-10/h1-4H |
| InChIKey | CJUCIKJLMFVWIS-UHFFFAOYSA-N |
| SMILES | C(=O)C1=CC(F)=CC=C1Br |
| CAS DataBase Reference | 94569-84-3(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36/37/39-24/25 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29130000 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | White to light yellow solid |
| Uses | 2-Bromo-5-fluorobenzaldehyde is used as a precursor for the synthesis of 5-fluoro-3-substituted benzoxaboroles, which is used in material science as molecular receptors, building block in crystal engineering, as steroid conjugates for molecular imprinting , dyes and biosensors of alpha hydroxyl carboxylic acids. It is also used in the synthesis of 5-arylindazolo[3,2-b]quinazolin-7(5H)-one by reacting with 2-amino-N'-arylbenzohydrazide in the presence of Copper(I) bromide by the Ullmann-type reaction. |
| Uses | 2-Bromo-5-fluorobenzaldehyde may be used in the synthesis of dihydrobenzoxaboroles bearing aryl, heteroaryl or vinyl substituents at the 1-position and 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole. |
| General Description | 2-Bromo-5-fluorobenzaldehyde can be prepared by reacting 2-bromo-5-fluorotoluene with N-bromosuccinimide. Its crystals exhibit monoclinic crystal system and space group P21/c. |
| Synthesis | 202865-66-5 94569-84-3 General procedure for the synthesis of 2-bromo-5-fluorobenzaldehyde from 2-bromo-5-fluorobenzyl alcohol: to a solution of 2-bromo-5-fluorobenzyl alcohol (0.852 g, 4.156 mmol) in dichloromethane (15 mL) was added manganese dioxide (4.254 g, 85%, 41.56 mmol). The reaction mixture was stirred at room temperature for 48 h. The solid was subsequently separated by filtration and washed with dichloromethane. The filtrate was concentrated to give 777 mg of 2-bromo-5-fluorobenzaldehyde (92% yield). Subsequently, the newly prepared 2-bromo-5-fluorobenzaldehyde (0.777 g, 3.828 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) and the solution was cooled to 0 °C. At low temperature, trifluoromethyltrimethylsilane (1.13 mL, 7.656 mmol) and tetrabutylammonium fluoride (0.020 g, 0.076 mmol) were added sequentially. After that, the reaction mixture was slowly warmed up to room temperature and stirring was continued at that temperature for 5 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed sequentially with water and brine and dried with magnesium sulfate. The solvent was removed under reduced pressure to afford 1.1 g (90% purity) of the crude product of 2-bromo-5-fluorophenyl-2,2,2-trifluoroethanol, which could be used in subsequent steps without further purification. |
| References | [1] New Journal of Chemistry, 2017, vol. 41, # 22, p. 13377 - 13381 [2] Patent: US2008/153852, 2008, A1. Location in patent: Page/Page column 23 [3] RSC Advances, 2014, vol. 4, # 25, p. 12834 - 12839 [4] Tetrahedron, 2015, vol. 71, # 38, p. 6744 - 6748 [5] Patent: CN104817441, 2017, B. Location in patent: Paragraph 0050-00053 |
2-Bromo-5-fluorobenzaldehyde Preparation Products And Raw materials
| Raw materials | 2-Bromo-5-fluorobenzyl alcohol-->2-Bromo-5-fluorobenzyl bromide-->Benzaldehyde, 3-fluoro-, O-methyloxime (9CI)-->Manganese dioxide-->Dichloromethane-->2-Bromo-5-fluorotoluene-->Methyl 2-bromo-5-fluorobenzoate-->4-Bromofluorobenzene-->3-Fluorobenzaldehyde |
| Preparation Products | 2-(2-bromo-5-fluorophenyl)acetaldehyde-->2-Bromo-5-fluorobenzoic acid-->6-Fluoro-1-indanone-->2-Bromo-5-fluorobenzenepropanoic acid-->5-fluoro-2-(2-phenylethynyl)benzaldehyde |
