4-Bromo-2,6-difluoroaniline
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4-Bromo-2,6-difluoroaniline
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CAS No:
67567-26-4
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Formula:
C6H4BrF2N
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Chemical Name:
4-Bromo-2,6-difluoroaniline
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Synonyms:
4-BROMO-2,6-DIFLUOROANILINE;2,6-DIFLUORO-4-BROMOANILINE;BUTTPARK 22\07-66;4-BROMO-2,6-DIFLUOROANILINE 99%;4-Bromo-2,6-difluoroaniline ,98%;4-Bromo-2,6-difluoro;2,6-difluro-4-broMoaniline;(4-BroMo-2,6-difluorophenyl)aMine
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CAS No:
Description
4-Bromo-2,6-difluoroaniline, brown crystalline powder, density is 1.8±0.1 g/cm3, boiling point is 188.2±35.0 °C at 760 mmHg, melting point is 63-65 °C (lit.), molecular formula is C6H4BrF2N, molecular weight is 208.003, flash point is 67.6±25.9 °C.
Characteristics
26
2.1
Brown Crystalline Powder
1.8±0.1 g/cm3
63-65 °C(lit.)
188.2°C at 760 mmHg
67.6±25.9 °C
1.570
Safety Information
IRRITANT
NONH for all modes of transport
3
20/21/22-36/37/38
26-36-36/37/39-22
Xn,Xi
Irritant
P261-P280-P305 + P351 + P338
H302 + H312 + H332-H315-H319-H335
|Warning|H302 (97.83%): 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|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4-Bromo-2,6-difluoroaniline Use and Manufacturing
b) Preparation of intermediate 2; 2, 6-difluorobenzeneamine (3.0g, 22.56 mmoles) was dissolved in acetic acid (10 ml). Bromine (1.2 ml) was added to the solution. The mixture was stirred for 15 minutes at room temperature. After evaporation of the solvent, the residue was treated with an aqueous solution of sodium carbonate. The aqueous solution was extracted with dichloromethane. The organic extract was dried over MgSC>4 and was evaporated. Yield : 92percent of intermediate 2.1a) 2, 6-Difluoroaniline (20.0 g, 0.15 mol, 1.0 eq) was dissolved in of glacial acetic acid (70 mL). The mixture was cooled with an ice bath and bromine (27.6 g, 0.16 mol, 1.1 eq) dissolved in acetic acid (10 mL) was added dropwise. During the addition the product precipitated. After stirring for 2 h at room temperature Na2SO3-solution (1.3 g Na2SO3 in 400 mL water) was added. The product was filtered off, washed with water and dried to afford a colorless solid (27.7 g, 84percent). TLC [Silica, DCM]: Rf = 0.71. 1H NMR (300 MHz, CDCl3): δ = 7.08-6.89 (m, 2H), 3.73 (s, 2H). 13C NMR (75 MHz, CDCl3): δ = 151.9 (dd, J = 244.1, 8.6 Hz), 123.6 (t, J = 16.2 Hz), 115.1-114.6 (m), 107.2 (t, J = 11.7 Hz). 19F NMR (282 MHz, CDCl3): δ = 131.1 (d, J = 7.1 Hz). LRMS (ESI): m/z 207.9 (calcd. 208.0 for C6H579BrF2N [M+H]To a solution of 2, 6-difluoroaniline (1 g, 7.75 mmol) in 20 mL of dry DCM was added NBS (1.96 g, 9.29mmol). The mixture was stirred at room temperature for 3 hours. The mixture was filtered andconcentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EA = 50/1 to 20/1) to afford the title compound (1.61 g, 80.7percent yield) as a yellow solid. LCMS (ESI) calc’d for C6H4BrF2N [M+H]: 208, found: 208.(i)
4-Bromo-2,6-difluoroaniline was used in synthesis of: 1) ammonium 5-bromo-7-fluorobenzo-2-oxa-1,3-diazole-4-sulphonate, fluorogenic derivatizating reagent for the determination of aminothiols by HPLC 2) olefin tolanes 3) 1-(4-amino-3,5-difluoro)-2-(4-butyloxyphenyl)ethyne 4) 4′′-n-butyloxy-3,5-difluoroterphenyl-4-amine 5) 4 -(3-methylbut-1-yn-3-ol)-2,6-difluoroaniline 6) potent VEGF receptor tyrosine kinase inhibitors.
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:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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