4-Bromo-2-methoxyphenol CAS 7368-78-7
4-Bromo-2-methoxyphenol Basic information
| Product Name: | 4-Bromo-2-methoxyphenol |
| Synonyms: | 4-BROMOGUAIACOL;4-BROMO-2-METHOXYPHENOL;AKOS 225-06;2-Methoxy-4-Bromophenol;4-Bromo-2-methoxyphenol,4-Bromoguaiacol;4-Bromo-2-methoxyphenol 98%;4-Bromoguaiacol, 5-Bromo-2-hydroxyanisole;B**4-Bromoguaiacol |
| CAS: | 7368-78-7 |
| MF: | C7H7BrO2 |
| MW: | 203.03 |
| EINECS: | |
| Product Categories: | Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;blocks;Bromides;Benzene series;Miscellaneous |
| Mol File: | 7368-78-7.mol |
4-Bromo-2-methoxyphenol Chemical Properties
| Melting point | 34-37 °C (lit.) |
| Boiling point | 129-132°C 12mm |
| density | 1.585±0.06 g/cm3(Predicted) |
| Fp | >230 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Chloroform, Methanol |
| pka | 9.40±0.18(Predicted) |
| form | Low Melting Solid or Crystalline Solid |
| color | Colorless to white to pale brown |
| Water Solubility | Slightly soluble in water. |
| BRN | 2045286 |
| InChI | InChI=1S/C7H7BrO2/c1-10-7-4-5(8)2-3-6(7)9/h2-4,9H,1H3 |
| InChIKey | WHSIIJQOEGXWSN-UHFFFAOYSA-N |
| SMILES | C1(O)=CC=C(Br)C=C1OC |
| CAS DataBase Reference | 7368-78-7(CAS DataBase Reference) |
| NIST Chemistry Reference | 4-Bromoguaiacol(7368-78-7) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| HS Code | 29095000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Uses | 4-bromo-2-methoxyphenol is an important organic intermediate (building block) to synthetize substituted phenzyl products, and it can also be used for the synthesis of polyfunctionalized bicyclic systems. |
| Uses | It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. |
| Uses | 4-Bromo-2-methoxyphenol is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.A. Schoenberg; R. F. Heck. Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides. J. Am. Chem. Soc. 1974, 96 (25), 7761-7764.Joel S. Freundlich; Howard E. Landis. An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols. Tetrahedron Letters. 2006, 47(25), 4275-4279. |
| Synthesis | 90-05-1 7368-78-7 General procedure for the synthesis of 4-bromo-2-methoxyphenol from guaiacol: NBu4Br3 (1.0 eq.) was dissolved in CH2Cl2 (ca. 5 mL/mmol NBu4Br3), which was immediately added to a CH2Cl2 solution (ca. 5 mL/mmol guaiacol) of guaiacol (1.0 eq.). The reaction mixture was stirred at 23 °C for 2 hours. Subsequently, the solvent was removed under reduced pressure (12 mbar, 40 °C). Water (5.0 mL) was added to the residue and the aqueous layer was extracted with Et2O (3 x 10 mL). The organic layer was separated and dried with MgSO4. The organic solvent was removed under reduced pressure (14 mbar, 40 °C) to give an oily residue, which was finally purified by silica gel column chromatography (SiO2, CH2Cl2). |
| References | [1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328 [2] Tetrahedron, 2014, vol. 71, # 1, p. 91 - 101 [3] Tetrahedron Letters, 1995, vol. 36, # 10, p. 1705 - 1708 [4] Synlett, 2012, vol. 23, # 7, p. 1082 - 1084 [5] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692 |
4-Bromo-2-methoxyphenol Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Diethyl ether-->N,N-Dimethylformamide-->PETROLEUM ETHER-->N-Bromosuccinimide-->Guaiacol-->Silane, (2-methoxyphenoxy)trimethyl--->Dichloromethane-->Tetrabutylammonium tribromide |
| Preparation Products | 2-METHOXY-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENOL-->4-Hydroxy-3-methoxybenzonitrile-->Phenol, 2-methoxy-4-(methylsulfonyl)--->Carbonochloridic acid, 4-bromo-2-methoxyphenyl ester-->4-bromo-1-hexoxy-2-methoxybenzene-->4-bromo-1-isopropoxy-2-methoxybenzene |
