2-(1-Adamantyl)-4-bromophenol CAS 104224-68-2

Introduction：Basic information about 2-(1-Adamantyl)-4-bromophenol CAS 104224-68-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

2-(1-Adamantyl)-4-bromophenol Basic information

• Product Name: 2-(1-Adamantyl)-4-bromophenol
• Synonyms: 2-(1-Adamantyl)-4-bromophenol (Adapalene);2-(1-Adamantyl)-4-br;4-BROMO-2-ADAMANTYL PHENOL;2-(2-adamantyl)-4-bromophenol;(2-ADAMANTYL)-4-BROMOPHENOL;2-(1-ADAMANTYL)-4-BROMOPHENOL;2-(Adamantan-1-yl)-4-bromophenol;2-ADAMANTANE-4-BROMOANISOLE
• CAS: 104224-68-2
• MF: C16H19BrO
• MW: 307.23
• Product Categories: Adamantane derivatives;Phenol&Thiophenol&Mercaptan;blocks;Bromides;APIs Intermediate
• Mol File: 104224-68-2.mol

2-(1-Adamantyl)-4-bromophenol Chemical Properties

• Melting point: 137-141
• Boiling point: 392.0±35.0 °C(Predicted)
• density: 1.442±0.06 g/cm3(Predicted)
• storage temp.: Inert atmosphere,Room Temperature
• pka: 9.56±0.43(Predicted)
• Appearance: Off-white to light yellow Solid
• InChI: InChI=1S/C16H19BrO/c17-13-1-2-15(18)14(6-13)16-7-10-3-11(8-16)5-12(4-10)9-16/h1-2,6,10-12,18H,3-5,7-9H2
• InChIKey: NYJXKHIVLGWPCF-UHFFFAOYSA-N
• SMILES: C1(O)=CC=C(Br)C=C1C12CC3CC(CC(C3)C1)C2
• CAS DataBase Reference: 104224-68-2(CAS DataBase Reference)

Safety Information

• Hazard Codes: Xi
• Hazard Note: Irritant
• HS Code: 2907290090

2-(1-Adamantyl)-4-bromophenol Usage And Synthesis

Chemical Properties

White powder

Uses

2-(Adamantan-1-yl)-4-bromophenol is an intermediate in the synthesis of Adapalene (A225000), a retinoid selective for retinoic acid receptor (RAR) subtypes β and γ; an antiacne agent.

Synthesis

106-41-2

768-95-6

104224-68-2

Preparation of 2-(1-adamantyl)-4-bromophenol (III): 4-bromophenol (10.0 g, 57.8 mmol) was dissolved in methanesulfonic acid (15 mL) with 1-adamantanol (8.78 g, 57.76 mmol), and the reaction was stirred for 3 hr at 70 °C. After completion of the reaction, the mixture was cooled to room temperature and diluted with deionized water (50 mL). The precipitated white solid was collected by filtration, washed several times with deionized water and subsequently dried to afford the target product 2-(1-adamantyl)-4-bromophenol (III). [Yield: 17 g, Yield: 97%]

References

[1] Bioorganic Chemistry, 2011, vol. 39, # 4, p. 151 - 158
[2] RSC Advances, 2016, vol. 6, # 73, p. 68560 - 68567
[3] Organic Process Research and Development, 2006, vol. 10, # 2, p. 285 - 288
[4] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 227 - 233
[5] Patent: WO2007/125542, 2007, A2. Location in patent: Page/Page column 13-14

2-(1-Adamantyl)-4-bromophenol Preparation Products And Raw materials

• Raw materials: 4-Bromophenol-->1-Adamantanol
• Preparation Products: 1-(5-Bromo-2-methoxy-phenyl)adamantane