2-Methyl-2-adamantanol Chemical Properties

Melting point:

214-218 °C

Boiling point:

234.5°C (rough estimate)

Density 

0.8802 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

Crystalline Powder

pka

14.99±0.20(Predicted)

color 

White

Water Solubility 

insoluble

InChI

InChI=1S/C11H18O/c1-11(12)9-3-7-2-8(5-9)6-10(11)4-7/h7-10,12H,2-6H2,1H3

InChIKey

JKOZWMQUOWYZAB-UHFFFAOYSA-N

SMILES

C12CC3CC(CC(C3)C1(C)O)C2

CAS DataBase Reference

702-98-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Methyl-2-adamantanol(702-98-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29029090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Methyl-2-adamantanol Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

2-Methyl-2-adamantanol is a chemical used in various research applications for the preparation of photoresist compositions.

Synthesis

Dissolve 2-adamantanone (1.50 g, 10 mmol) in ether under nitrogen protection and cool to 0°C. Methyl lithium solution (7.5 mL, 1.6 M in ether, 12 mmol) was added slowly and dropwise. The reaction mixture was continued to be stirred at 0 °C for 1 h, then brought to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the addition of saturated ammonium chloride solution and extracted three times with ether. The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: dichloromethane to 5% methanol/dichloromethane) to afford 2-methyl-2-adamantanol (56) as a white solid (1.58 g, 95% yield).1H-NMR (360 MHz, CDCl3) δ 2.20-2.16 (m, 2H), 1.89-1.75 (m, 6H), 1.68 ( br s, 4H), 1.57-1.54 (m, 2H), 1.48 (br s, 1H), 1.35 (s, 3H); 13C-NMR (90 MHz, CDCl3) δ 74.06, 39.30, 38.49, 35.33, 33.16, 27.73, 27.60, 27.22; ESI-MS: C11H18O(M+H)+ calculated value 167.3, measured value 167.3.

References

[1] Patent: WO2011/22191, 2011, A1. Location in patent: Page/Page column 34
[2] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 147 - 150
[3] Zhurnal Obshchei Khimii, 1987, vol. 57, # 1, p. 171 - 174
[4] Journal of the American Chemical Society, 1968, vol. 90, # 18, p. 4929 - 4939
[5] Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 1981, vol. 37, p. 129 - 134

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