2-bromo-3-methyl-phenol CAS 22061-78-5
2-bromo-3-methyl-phenol Basic information
| Product Name: | 2-bromo-3-methyl-phenol |
| Synonyms: | 2-bromo-3-methyl-phenol;2-Bromo-3-hydroxytoluene;Phenol, 2-broMo-3-Methyl-;2-Bromo-3-methylphenol 98%;2-bromo-3-methyl-phenol USP/EP/BP |
| CAS: | 22061-78-5 |
| MF: | C7H7BrO |
| MW: | 187.03 |
| EINECS: | |
| Product Categories: | Halides;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het |
| Mol File: | 22061-78-5.mol |
2-bromo-3-methyl-phenol Chemical Properties
| Melting point | 58.5-59 °C |
| Boiling point | 83-84 °C(Press: 4 Torr) |
| density | 1.554±0.06 g/cm3(Predicted) |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| form | Solid |
| pka | 8.54±0.10(Predicted) |
| color | Light Brown |
Safety Information
| HS Code | 2907199090 |
| Uses | 2-Bromo-3-methylphenol is a reagent used in chemoselective and regioselective oxybromination of phenols with dioxygen |
| Synthesis | 2835-97-4 22061-78-5 Step 1: 2-Amino-3-methylphenol (8a, 5.7 g, 46.3 mmol) was dissolved in a solvent mixture of water (30 mL) and 1,4-dioxane (15 mL). The reaction mixture was heated to reflux followed by slow dropwise addition of hydrobromic acid (48%, 17 mL, 0.31 mol) over 20 min. After the dropwise addition was completed, the reaction was continued at reflux for 15 min. The reaction solution was cooled to 0 °C and an aqueous solution of sodium nitrite (20 mL) was added over 30 min. Stirring was continued at 0 °C for 15 min, after which the reaction mixture was poured at once into a mixture of water (20 mL) and hydrobromic acid (48%, 17 mL, 0.31 mol) of cuprous bromide (I) (7.64 g, 53.2 mmol) that had been pre-cooled to 0 °C and treated to avoid light. After stirring at 0 °C for 15 min, the reaction solution was slowly warmed to 60 °C and stirring was continued for 15 min. It was then cooled to room temperature and stirred overnight. Upon completion of the reaction, the mixture was transferred to a partition funnel and extracted with ethyl acetate (3×). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. Purification by CombiFlash fast chromatography system (eluent: 20% ethyl acetate/hexane) gave the target product 2-bromo-3-methylphenol (8b, 1.46 g, 17% yield) as a reddish brown oil. |
| References | [1] Patent: WO2009/62285, 2009, A1. Location in patent: Page/Page column 60-61 [2] Patent: WO2009/62308, 2009, A1. Location in patent: Page/Page column 70 [3] Patent: WO2009/62288, 2009, A1. Location in patent: Page/Page column 67 [4] Patent: WO2009/62289, 2009, A1. Location in patent: Page/Page column 74 [5] Journal of the Chemical Society, 1925, vol. 127, p. 498 |
2-bromo-3-methyl-phenol Preparation Products And Raw materials
| Raw materials | 2-Amino-3-methylphenol-->Sodium nitrite-->Water-->Hydrogen bromide-->1,4-Dioxane-->Cuprous bromide |
| Preparation Products | 4-Bromo-3-methylphenol-->2-HYDROXY-6-METHYL-BENZONITRILE |
