| Identification | More | [Name]
5-BROMO-2-METHOXYANILINE | [CAS]
6358-77-6 | [Synonyms]
5-BROMO-2-METHOXYANILINE
5-bromo-2-methoxybenzenamine
2-amino-4-bromoanisole
5-bromo-o-anisidine | [Molecular Formula]
C7H8BrNO | [MDL Number]
MFCD04037882 | [Molecular Weight]
202.05 | [MOL File]
6358-77-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
94-96°C | [Boiling point ]
275℃ | [density ]
1.531 | [Fp ]
120℃ | [storage temp. ]
2-8°C | [form ]
powder to crystal | [pka]
3.46±0.10(Predicted) | [color ]
Light yellow to Brown | [Water Solubility ]
Slightly soluble in water. | [InChI]
InChI=1S/C7H8BrNO/c1-10-7-3-2-5(8)4-6(7)9/h2-4H,9H2,1H3 | [InChIKey]
OPGNSNDTPPIYPG-UHFFFAOYSA-N | [SMILES]
C1(N)=CC(Br)=CC=C1OC | [CAS DataBase Reference]
6358-77-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R33:Danger of cumulative effects. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S33:Take precautionary measures against static discharges .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN2811 | [WGK Germany ]
3 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2921490090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white powder | [Uses]
5-Bromo-2-methoxyaniline is used as a pharmaceutical intermediate. | [Synthesis]
General procedure for the synthesis of 5-bromo-2-methoxyaniline from 2-nitro-4-bromoanisole:
1. Preparation of Intermediate 11A: An ethanol (65 mL) solution of 4-bromo-1-methoxy-2-nitrobenzene (2.00 g, 8.62 mmol), zinc powder (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) was stirred for 2 hours at room temperature.
2. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and filtered through diatomaceous earth (CELITE).
3. The filtrate was concentrated by evaporation to give Intermediate 11A (1.74 g, 100% yield) as an off-white solid.
4. Mass spectral analysis (LCMS-ESI) of Intermediate 11A showed m/z 202,204 ([M+H]? , [M+2+H]?) , and a retention time (RT) of 0.70 min (Method J). | [References]
[1] Patent: WO2014/22343, 2014, A1. Location in patent: Paragraph 00169
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1357 - 1366
[3] Journal fuer Praktische Chemie (Leipzig), 1935, vol. <2> 143, p. 18,24
[4] Gazzetta Chimica Italiana, 1932, vol. 62, p. 51,54
[5] Justus Liebigs Annalen der Chemie, 1883, vol. 217, p. 44 |
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