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

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(104224-68-2)Related Product Information

• 3-Bromophenol
• 4-Bromophenol
• Bromophenol Blue
• 1-[2-(Benzyloxy)-5-bromophenyl]adamantane
• 2-Adamantyl-4-bromo-1-(2,2,2-trifluoroethoxy)benzene
• 1-(5-Bromo-2-methoxy-phenyl)adamantane
• 1-Bromo-3-n-hexylbenzene, 97+%
• 1-Phenyladamantane
• 3-tert-butylbromobenzene
• Adapalene
• 4-Bromoanisole
• Adamantane
• bromophenol
• 4-(1-ADAMANTYL)-2-BROMOPHENOL
• 2-(1-Adamantyl)-4-bromophenol