4-BROMO-3,5-DIMETHYLANILINE
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4-BROMO-3,5-DIMETHYLANILINE
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CAS No:
59557-90-3
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Formula:
C8H10BrN
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Chemical Name:
4-BROMO-3,5-DIMETHYLANILINE
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Synonyms:
4-Bromo-3,5-dimethylbenzenamine;4-Bromo-3,5-xylidine;5-Amino-2-bromo-m-xylene;BenzenaMine, 4-broMo-3,5-diMethyl-
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CAS No:
Characteristics
26
3.4
1.4±0.1 g/cm3
73-74°C
261°C at 760 mmHg
111.6±25.9 °C
1.597
Room temperature.
4-BROMO-3,5-DIMETHYLANILINE Use and Manufacturing
To a solution of 3, 5-dimethylaniline (3.0 ml, 24 mmol) in ice cold dichloromethane (200 ml) was added trifluoroacetic anhydride (4.18mL, 1.25 equivs). After 30 minutes, bromine (1.2 ml, 0.97 equivs) was slowly added over 5 minutes. After aqueous work-up and drying in vacuo the recovered crude (6.81 g, 96percent) was taken up in dry THF (40 ml). The solution was cooled to -78To a solution of 3, 5-dimethylaniline 1a (80 g, 660 mmol) in 800 mL MeCN was added a solution of NBS (117g, 660mmol) in 400 ml MeCN at ice-bath, stirred at room temperature for 16h. The reaction mixture was concentratedunder reduced pressure. The residue was purified by silica column chromatography (Eluent C) to give title product 4-bromo-3, 5-dimethylaniline 1b (90 g, yellow solid), yield: 68.2percent.MS m/z (ESI): 200 [M+1]First, 3, 5-dimethyl aniline (10.0 g, 82.5 mmol) was dissolved in MeCN. NBS (15.4 g, 86.6 mmol) was added and the reaction mixture was stirred for two days at room temperature.Reference Example 19 [0622] [0623] N-Bromosuccinimide (1.78 g) was added to 3, 5-dimethylaniline (1.21 g) in acetonitrile (50 mL) and the mixture was stirred at room temperature for 8 hours. The reaction solution was concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 19-1 (1.78 g). A mixture of compound 19-1 (100 mg), tris(dibenzylideneacetone)dipalladium (0) (23 mg), 2-dicyclohexylphosphino-2′, 6-dimethoxybiphenyl (41 mg), potassium phosphate (424 mg) and 2-(trifluoromethyl)phenylboronic acid (190 mg) was stirred in toluene (1.0 mL) at 100° C. for 32 hours. After cooling to room temperature, the reaction solution was diluted with ethyl acetate and filtered. The filtrate was concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 19-2 (51 mg). Compound 19-1:
Computed Properties
Molecular Weight:200.08
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:198.99966
Monoisotopic Mass:198.99966
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:104
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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