| Identification | Back Directory | [Name]
N-(TERT-BUTOXYCARBONYL)-2-BROMOANILINE | [CAS]
78839-75-5 | [Synonyms]
N-Boc 2-broMoaniline
tert-Butyl (2-bromophenyl)
ert-butylN-(2-bromophenyl)carbamate
tert-butyl (2-broMophenyl)carbaMate
TERT-BUTYL N-(2-BROMOPHENYL)CARBAMATE
2-Bromo-N-(tert-butoxycarbonyl) aniline
N-(tert-Butoxycarbonyl)-2-bromoaniline 97%
Carbamic acid, N-(2-bromophenyl)-, 1,1-dimethylethyl ester | [Molecular Formula]
C11H14BrNO2 | [MDL Number]
MFCD01006614 | [MOL File]
78839-75-5.mol | [Molecular Weight]
272.14 |
| Chemical Properties | Back Directory | [Boiling point ]
110 °C0.3 mm Hg(lit.) | [density ]
1.342 g/mL at 25 °C(lit.) | [refractive index ]
n20/D 1.54(lit.) | [Fp ]
>230 °F | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
12.93±0.70(Predicted) | [Appearance]
Light yellow to light brown Liquid | [InChI]
1S/C11H14BrNO2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8(9)12/h4-7H,1-3H3,(H,13,14) | [InChIKey]
UQBGKDLSIIHUEZ-UHFFFAOYSA-N | [SMILES]
CC(C)(C)OC(=O)Nc1ccccc1Br |
| Hazard Information | Back Directory | [Uses]
N-(tert-Butoxycarbonyl)-2-bromoaniline may be used in the synthesis of N-boc-protected o-aryl anilines, which undergoes coupling reaction with bromoacetylenes to form the corresponding arene?ynamides. | [General Description]
N-(tert-Butoxycarbonyl)-2-bromoaniline, also known as tert-butyl-N-(2-bromophenyl)carbamate, is an N-Boc-protected o-bromoaniline.1 It reacts with ethyl perfluorooctanoate in the presence of tert-butyllithium to form the corresponding 1-hydroxy-1H-perfluorooctyl compound. | [Synthesis]
The general procedure for the synthesis of N-(tert-butoxycarbonyl)-2-bromoaniline from di-tert-butyl dicarbonate and o-bromoaniline: di-tert-butyl dicarbonate (10.90 g, 50 mmol) was added to a solution of 2-bromoaniline (3.43 g, 20 mmol) in tetrahydrofuran (THF, 40 mL), followed by stirring of the reaction mixture for 3 days under reflux conditions. Upon completion of the reaction, the mixture was diluted by adding ether (50 mL), and the organic phase was washed sequentially with saturated sodium chloride solution (50 mL x 3) and dried with anhydrous magnesium sulfate (MgSO?). The solvent was removed by concentration under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography with the eluent of petroleum ether/ethyl acetate (20:1, v/v), and tert-butyl N-(2-bromophenyl)carbamate (4.73 g, 87% yield) was finally obtained. | [References]
[1] Organic Letters, 2009, vol. 11, # 22, p. 5130 - 5133
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 8, p. 1867 - 1880
[3] Journal of Organic Chemistry, 2008, vol. 73, # 14, p. 5658 - 5661
[4] Heterocycles, 1996, vol. 43, # 12, p. 2741 - 2746
[5] Tetrahedron Letters, 2007, vol. 48, # 47, p. 8318 - 8322 |
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