| Identification | Back Directory | [Name]
6-BROMO-O-CRESOL | [CAS]
13319-71-6 | [Synonyms]
6-BROMO-O-CRESOL
6-Bromo-o-cresol >
2-Bromo-6-methylphenol
6-Bromo-o-cresol
Phenol,2-broMo-6-Methyl-
2-Bromo-6-methylphenol96%
2-Bromo-6-methylphenol 96%
6-BroMo-o-cresol,2-BroMo-6-Methylphenol
3-Bromo-2-hydroxytoluene, 6-Bromo-o-cresol | [Molecular Formula]
C7H7BrO | [MDL Number]
MFCD09907876 | [MOL File]
13319-71-6.mol | [Molecular Weight]
187.03 |
| Chemical Properties | Back Directory | [Melting point ]
16 °C | [Boiling point ]
208 °C | [density ]
1.51 | [refractive index ]
1.5680-1.5720 | [Fp ]
80° | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
clear liquid | [pka]
8.78±0.10(Predicted) | [color ]
Colorless to Light orange to Yellow | [InChIKey]
YXZPTVOCJLCMRO-UHFFFAOYSA-N | [CAS DataBase Reference]
13319-71-6 |
| Hazard Information | Back Directory | [Uses]
6-Bromo-o-cresol is used as an organic reagent in organic synthesis and scientific research.
| [Hazard]
6-Bromo-o-cresol is harmful if swallowed or inhaled, it causes skin irritation and serious eye irritation.
| [Synthesis]
The general procedure for the synthesis of 2-bromo-6-methylphenol from o-cresol is as follows:
Example 36 Synthesis of 2-bromo-6-methylphenol
To a dichloromethane (500 mL) solution of o-cresol (20.0 g, 0.19 mol) and diisopropylamine (2.63 mL, 18.5 mmol), a dichloromethane (500 mL) solution of N-bromosuccinimide (NBS, 32.9 g, 0.19 mol) was slowly added dropwise, and the dropwise process lasted for 7 hours. After completion of the titration, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was acidified to pH=1 with concentrated hydrochloric acid and subsequently diluted by adding sulfuric acid and water (400 mL). The organic layer was separated, dried with anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent to give 34.6 g of crude product in 97% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.30 (s, 3H), 5.54 (s, 2H), 6.71 (t, J=7.6 Hz, 1H), 7.05 (d, J=7.6 Hz, 1H), 7.28 (d, J=8.0 Hz, 1H). | [References]
[1] Advanced Synthesis and Catalysis, 2008, vol. 350, # 9, p. 1309 - 1315
[2] Patent: US2009/203657, 2009, A1. Location in patent: Page/Page column 51
[3] Patent: US2009/197871, 2009, A1. Location in patent: Page/Page column 54
[4] Chemistry - A European Journal, 2018, vol. 24, # 10, p. 2379 - 2383
[5] Tetrahedron Letters, 1998, vol. 39, # 19, p. 2947 - 2950 |
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