2-(2-Bromophenyl)-2-propanol Chemical Properties

Boiling point:

128-130 °C

Density 

1.403±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

14.08±0.29(Predicted)

form 

liquid

color 

Yellow

InChI

InChI=1S/C9H11BrO/c1-9(2,11)7-5-3-4-6-8(7)10/h3-6,11H,1-2H3

InChIKey

TXQKNSQVEWHJAQ-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1Br)(O)(C)C

Safety Information

HS Code 

2905599890

2-(2-Bromophenyl)-2-propanol Usage And Synthesis

Synthesis

To a solution of 26.50 g (0.14 mol) of ethyl 2-bromobenzoate (4a) dissolved in 35 mL of anhydrous diethyl ether at -5°C was slowly added methylmagnesium iodide Grignard's reagent prepared from 9.1 g (0.37 mol) of magnesium and 53.3 g (0.37 mol) of freshly distilled methyl iodide in 85 mL of anhydrous ether. Upon completion of the reaction, the reaction was quenched by the addition of 38% ammonium chloride solution (58 mL). The ether layer was separated by decantation and the remaining pasty precipitate was extracted with ether (3 x 35 mL). All ether layer extracts were combined and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The product 2-(2-bromophenyl)-2-propanol 19.40 g was obtained in 82% yield and 95% purity (GLC assay). Physical properties of the product: boiling point 99-100 °C (5 mmHg), d420=1.1576, nD20=1.5420; MRD measured value 46.43, calculated value 46.55. Comparison of literature data: melting point 23.7 °C, boiling point 79.2 °C (2.2 mmHg), nD20=1.5416. IR spectra characteristic absorption peaks (ν, cm-1) : 3460, 1175 (OH), 1370, 1385 [C(CH3)2], 690 (C-Cl).1H NMR spectral data (δ, ppm): 1.64s (6H, CH3), 2.46s (1H, OH), 6.9-7.7m (4H, Harom). Elemental analysis measured values (%): C 63.00, H 6.42, Cl 20.71; calculated values (%) for molecular formula C9H11ClO: C 63.35, H 6.50, Cl 20.78.

References

[1] Organic Letters, 2013, vol. 15, # 20, p. 5326 - 5329
[2] Russian Journal of Organic Chemistry, 2016, vol. 52, # 6, p. 806 - 812
[3] Zh. Org. Khim., 2016, vol. 52, # 6, p. 806 - 812,7
[4] Transactions of the Faraday Society, 1936, vol. 32, p. 1327,1328 Anm.

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