| Identification | More | [Name]
3-Bromo-2-methylaniline | [CAS]
55289-36-6 | [Synonyms]
2-AMINO-6-BROMOTOLUENE
3-BROMO-2-METHYLANILINE
Benzenamine, 3-bromo-2-methyl-
2-Amino-6-bromotoluene~3-Bromo-o-toluidine
3-bromo-o-toluidine
2-AMINO-6-BROMOTOLUENE ( 3-BROMO-2-METHYLANILINE )
2-Bromo-6-Aminotoluene,2-Amino-6-Bromotoluene
2-BROMO-6-AMINOTOLUENE
3-BROMO-2-METHYLANILINE/2-AMINO-6-BROMOTOLUENE
3-BROMO-2-METHYLANILINE, 98+%
3-Bromo-2-methylbenzenamine | [EINECS(EC#)]
259-568-5 | [Molecular Formula]
C7H8BrN | [MDL Number]
MFCD00051579 | [Molecular Weight]
186.05 | [MOL File]
55289-36-6.mol |
| Chemical Properties | Back Directory | [Boiling point ]
248 °C (lit.) | [density ]
1.51 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.619(lit.)
| [Fp ]
230 °F
| [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Liquid | [pka]
3.38±0.10(Predicted) | [color ]
Clear colorless to yellow to pale brown | [Sensitive ]
Light Sensitive | [BRN ]
2354213 | [InChI]
InChI=1S/C7H8BrN/c1-5-6(8)3-2-4-7(5)9/h2-4H,9H2,1H3 | [InChIKey]
IILVSKMKMOJHMA-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=CC(Br)=C1C | [CAS DataBase Reference]
55289-36-6(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Bromo-2-methylaniline(55289-36-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
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:Wear suitable protective clothing . | [RIDADR ]
2810 | [WGK Germany ]
3
| [Hazard Note ]
Harmful/Irritant | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29214300 |
| Questions And Answer | Back Directory | [Application]
3-Bromo-2-methylaniline is a 3-halo-2-methylaniline derivative. 3-bromo-2-methylaniline is an important organic intermediate (building block) to synthetize substituted aniline products. 3-Bromo-2-methylaniline may be used in the preparation of 3,4-dibromo-2-methylaniline, racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Tröger’s base, 4-bromo-1H-indazole, and so on.
|
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to pale brown liquid | [Uses]
3-Bromo-2-methylaniline may be used in the preparation of :
- 3,4-dibromo-2-methylaniline
- racemic 3,9-dibromo-4,10-dimethyl-6H,12H,5,11-methanodibenzodiazocine, a racemic derivative of Tr?ger′s base
- 4-bromo-1H-indazole
| [General Description]
3-Bromo-2-methylaniline is a 3-halo-2-methylaniline derivative. | [Synthesis]
General procedure for the synthesis of 3-bromo-2-methylaniline from 2-bromo-6-nitrotoluene: 2-bromo-6-nitrotoluene (500 mg, 2.32 mmol) and stannous dichloride hydrate (2.62 g, 11.63 mmol) were dissolved in ethanol, and the reaction was stirred for 3 hours at 80°C. After completion of the reaction, ethanol was removed by rotary evaporation. Subsequently, the pH of the reaction mixture was adjusted with saturated aqueous sodium bicarbonate to about 8. The mixture was filtered through diatomaceous earth and the filter cake was washed with ethyl acetate. The filtrates were combined and extracted three times with ethyl acetate. Finally, the combined organic phases were dried by rotary evaporation to give 3-bromo-2-methylaniline (410 mg, 2.20 mmol) in 95% yield. | [References]
[1] Tetrahedron, 2008, vol. 64, # 13, p. 2938 - 2950
[2] Synlett, 2009, # 15, p. 2483 - 2486
[3] Chemical Communications, 2003, # 10, p. 1170 - 1171
[4] Organic Letters, 2011, vol. 13, # 19, p. 5220 - 5223
[5] Patent: EP3412657, 2018, A1. Location in patent: Paragraph 0104; 0108 |
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