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2-Methyl-2-adamantanol

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2-Methyl-2-adamantanol manufacturers

2-Methyl-2-adamantanol Basic information
Product Name:2-Methyl-2-adamantanol
Synonyms:2-Adamantanol, 2-methyl-;Tricyclo(3.3.1.1(3,7))decan-2-ol, 2-methyl-;AKOS BC-0511;2-METHYL-ADAMANTAN-2-OL;2-HYDROXY-2-METHYLADAMANTANE;2-METHYL-2-ADAMANTANOL;2-METHYL-2-ADAMANTOL;RARECHEM AQ TC 1054
CAS:702-98-7
MF:C11H18O
MW:166.26
EINECS:999-999-2
Product Categories:Stains and Dyes;Stains&Dyes, A to;Adamantane derivatives;Adamantanes;M;Adamantane Derivative
Mol File:702-98-7.mol
2-Methyl-2-adamantanol Structure
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
pka14.99±0.20(Predicted)
color White
Water Solubility insoluble
InChIInChI=1S/C11H18O/c1-11(12)9-3-7-2-8(5-9)6-10(11)4-7/h7-10,12H,2-6H2,1H3
InChIKeyJKOZWMQUOWYZAB-UHFFFAOYSA-N
SMILESC12CC3CC(CC(C3)C1(C)O)C2
CAS DataBase Reference702-98-7(CAS DataBase Reference)
NIST Chemistry Reference2-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 Information
ProviderLanguage
ACROS English
ALFA English
2-Methyl-2-adamantanol Usage And Synthesis
Chemical Propertieswhite crystalline powder
Uses2-Methyl-2-adamantanol is a chemical used in various research applications for the preparation of photoresist compositions.
Synthesis
2-Adamantanone

700-58-3

Methyllithium

917-54-4

2-Methyl-2-adamantanol

702-98-7

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
2-Methyl-2-adamantanol Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->Magnesium-->Methyl bromide-->2-Adamantanone-->Methylmagnesium chloride-->Methyllithium
Preparation Products2-Ethyl-2-adamantyl methacrylate-->AKOS BC-0207
Tag:2-Methyl-2-adamantanol(702-98-7) Related Product Information
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