| Identification | More | [Name]
4-(TERT-BUTYL)-2-NITROANILINE | [CAS]
6310-19-6 | [Synonyms]
4-(TERT-BUTYL)-2-NITROANILINE
BUTTPARK 52\04-96
2-Nitro-4-tert-butylaniline
4-(1,1-Dimethylethyl)-2-nitrobenzenamine | [EINECS(EC#)]
228-632-4 | [Molecular Formula]
C10H14N2O2 | [MDL Number]
MFCD00066305 | [Molecular Weight]
194.23 | [MOL File]
6310-19-6.mol |
| Safety Data | Back Directory | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
2811 | [HazardClass ]
6.1 | [PackingGroup ]
Ⅱ | [HS Code ]
2921420090 |
| Hazard Information | Back Directory | [Uses]
4-(tert-Butyl)-2-nitroaniline is an organic compound commonly used in organic synthesis, especially as a synthetic intermediate in the pharmaceutical and dye industries. | [Synthesis]
General procedure for the synthesis of 4-tert-butyl-2-nitroaniline from N-(4-tert-butyl-2-nitrophenyl)acetamide: Methanol (13.5 L) and N-(4-tert-butyl-2-nitrophenyl)acetamide (7.0 kg, 29.6 mol) were added to the reactor. The mixture was stirred for 10 min, then a methanol solution of 30% sodium methanol (6.49 L, 35.5 mol) was slowly added at room temperature. The mixture was slowly heated to reflux and held at this temperature for 2 hours. Upon completion of the reaction, the methanol was vacuum distilled to dryness at 50-55°C and the solid was cooled to room temperature. The residue was stirred in water (35 L) for 1 h. The solid was collected by filtration, washed with water (14 L) and dried at 45-50 °C to give 5.3 kg of 4-tert-butyl-2-nitroaniline. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.27 (s, 9H), 5.95 (br s, 2H), 6.76 (d, 1H), 7.43 (d, 1H), 8.08 (s, 1H). | [References]
[1] Journal of the American Chemical Society, 2012, vol. 134, # 3, p. 1528 - 1535
[2] Journal of Organic Chemistry, 1970, vol. 35, p. 917 - 923
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 25, p. 4906 - 4916
[4] Patent: WO2011/47315, 2011, A1. Location in patent: Page/Page column 51
[5] Patent: WO2013/114250, 2013, A1. Location in patent: Page/Page column 181 |
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