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| | 5-Bromo-2-chlorobenzoic acid Basic information |
| | 5-Bromo-2-chlorobenzoic acid Chemical Properties |
| Melting point | 154-156 °C (lit.) | | Boiling point | 324.5±27.0 °C(Predicted) | | density | 1.7312 (rough estimate) | | refractive index | 1.5590 (estimate) | | storage temp. | Sealed in dry,Room Temperature | | solubility | 2.63g/l | | pka | 2.49±0.25(Predicted) | | form | Solid | | color | Off white colored powder | | Water Solubility | Soluble in water 2.63 g/L @20°C. | | BRN | 2691432 | | InChI | InChI=1S/C7H4BrClO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11) | | InChIKey | FGERXQWKKIVFQG-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC(Br)=CC=C1Cl | | CAS DataBase Reference | 21739-92-4(CAS DataBase Reference) | | NIST Chemistry Reference | 5-Bromo-2-chlorobenzoic acid(21739-92-4) | | EPA Substance Registry System | Benzoic acid, 5-bromo-2-chloro- (21739-92-4) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29163900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-Bromo-2-chlorobenzoic acid Usage And Synthesis |
| Description | 5-Bromo-2-chlorobenzoic acid (BCBA) is an organic reagent that can be used in electroinduced dehalogenation reactions. Ag/Cu electrodes exhibit high electrocatalytic activity in the dehalogenation reaction of BCBA. The process is characterised by a sequence of halide excretion and hydrogen addition. Since the bond dissociation energy value of C-Br bond is smaller than that of C-Cl bond, Br-w is more easily released from the benzene ring. As C-Br breaks, BCBA gains electrons and hydrogen to form the intermediate 2-chlorobenzoate. C-Cl then breaks in the same way to give the final product benzoate.
 | | Chemical Properties | white to light yellow crystal powder | | Uses | 5-Bromo-2-chlorobenzoic acid was used to evaluate the homogeneity of organic powder. It can be used to produce 2-chloro-5-deuteriobenzoic acid. | | Synthesis | 4.7g (0.03 mol) of 2-chlorobenzoic acid, 40mL of concentrated sulfuric acid and 0.936g (0.012 mol) of sodium sulfide are sequentially added into a 250mL four-mouth bottle, stirred for 20 minutes at 30 ℃ until the solution is clear, then 5.334g N-bromosuccinimide (0.03 mol) is added, the reaction is continued for 10 minutes at 30 ℃, and then the solution is slowly poured into 80mL ice water bath for crystallization to obtain a crude product of the 5-bromo-2-chlorobenzoic acid. Add the filter cake into a 250mL four-mouth bottle, add 24mL methanol and 36mL water, heat to 60 ℃, naturally cool, and stir for crystallization. Filtration, washing with 20mL of 40% volume fraction aqueous methanol, and drying at 55 ℃ for 6 hours gave 6.001g of a white solid, yield: 85.0%. | | References |
[1] Fen Wang . “The Electroreductive Dehalogenation Reaction of 5-Bromo-2-chlorobenzoic Acid on Dendritic Ag/Cu.” International Journal of Electrochemical Science 10 6 (2015): Pages 5101-5111.
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| | 5-Bromo-2-chlorobenzoic acid Preparation Products And Raw materials |
| Raw materials | 2-Chlorobenzoic acid-->5-Bromosalicylic acid-->2-Chlorobenzotrichloride-->5-BROMO-2-CHLORO-BENZOYL CHLORIDE-->Sulfuric acid-->Acetic acid-->Sodium bromide-->Sodium periodate | | Preparation Products | 5'-BROMO-2'-CHLOROACETOPHENONE-->5-BROMO-2-CHLORO-BENZOYL CHLORIDE-->Bexagliflozin-->ETHYL 5-BROMO-2-CHLOROBENZOATE-->4-(5-broMo-2-chlorobenzyl)phenol-->2-(5-Bromo-2-chloro-phenyl)-1H-benzoimidazole-->(5-bromo-2-chlorophenyl)(4-fluorophenyl)methanone-->5-Bromo-2-chloro-N-cyclopropylbenzamide-->[1,1'-Biphenyl]-3-carboxylic acid, 4-chloro-3'-fluoro--->2,5-Bis(2,2,2-trifluoroethoxy)benzoic acid-->(2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-ethoxyphenyl)(methoxy) methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol-->(5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone |
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