4-Bromo-2,3-difluorobenzenamine
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4-Bromo-2,3-difluorobenzenamine
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CAS No:
112279-72-8
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Formula:
C6H4BrF2N
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Chemical Name:
4-Bromo-2,3-difluorobenzenamine
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Synonyms:
Benzenamine,4-bromo-2,3-difluoro-;4-Bromo-2,3-difluorobenzenamine;4-Bromo-2,3-difluoroaniline;(4-Bromo-2,3-difluorophenyl)amine
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CAS No:
Safety Information
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
4-Bromo-2,3-difluorobenzenamine Use and Manufacturing
To a solution of 2, 3-difluoroaniline (G-1) (38.0 ml, 375 mmol) in anhydrous dimethylformamide (20 ml) was added NBS (70.1 g, 394 mmol) with ice-cooling, then the reaction mixture was stirred for 1 hour. To the reaction solution was added water, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to give Compound (G-2) (81.9 g, quant.) as an oil.Compound (G-2);Method C: Rt=1.81 min, 207.65 (ES+)4-Bromo-2, 3-difluoroaniline Step 1: 4-bromo-2, 3-difluoroanilinThe procedure for preparing this compound was based on that described in International Patent Publication No. WO 2010/091272. To a 100 mL round bottom flask, 2, 3-difluoroaniline (1 g, 0.0077 mol) and ACN (30 mL) were added. To the flask was added the solution of tetrabutylammonium tribromide (3.71 g, 0.0077 mol, in 10 mL of ACN). The reaction mixture was stirred at room temperature for 3 h. The reaction mass was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and evaporated under reduced pressure to get the crude product. The crude product was purified by column chromatography using 60-12 silica gel and 30percent ethyl acetate in hexane to get the title compound [0.55 g, 34percent]. The obtained product was immediately taken to the next step.Example 124: Preparation of N-{4-(4-bromo-2, 3-difluoro-phenylamino)-7-[2- (2-dimethylamino-acetylamino)-ethoxy]-quinazolin-6-yl}-acrylamide<124-1> 4-bromo-2, 3-difluoro-phenylamine; 2, 3-difluoro-phenylamine (13.45 g, 104.2 mmol) was diluted with acetic acid (180 mi), bromine (2.6 mi) diluted with acetic acid (5 mi) was slowly added thereto at 0 'C , and the solution was stirred for 5 hours. The resulting solution was distilled under a reduced pressure to remove the solvent, basified by adding 50percent sodium hydroxide solution (250 mi), and extracted with dichloromethane (200 mi) twice. The separated organic layer was dried over magnesium sulfate, filtered and distilled under a reduced pressure to obtain the title compound 6.46 g (yield: 30percent).
Computed Properties
Molecular Weight:208.00
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:206.94952
Monoisotopic Mass:206.94952
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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